CA2531088A1 - Photochromic compounds - Google Patents

Photochromic compounds Download PDF

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CA2531088A1
CA2531088A1 CA002531088A CA2531088A CA2531088A1 CA 2531088 A1 CA2531088 A1 CA 2531088A1 CA 002531088 A CA002531088 A CA 002531088A CA 2531088 A CA2531088 A CA 2531088A CA 2531088 A1 CA2531088 A1 CA 2531088A1
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alkyl
chosen
phenyl
substituted
alkoxy
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CA2531088C (en
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Anil Kumar
Meng He
Terry A. Ii Kellar
Forrest R. Blackburn
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Transitions Optical Inc
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Transitions Optical, Inc.
Anil Kumar
Meng He
Terry A. Ii Kellar
Forrest R. Blackburn
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    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

Various non-limiting embodiments disclosed herein relate generally to photochromic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. Other non-limiting embodiments relate to photochromic-dichroic compounds, which may be thermally reversible or non-thermally reversible, and articles made therefrom. For example, one non-limiting embodiment provides a thermally reversible, photochromic compound adapted to have at least a first state and a second state, wherein the thermally reversible, photochromic compound has an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD.
Another non-limiting embodiment provides a photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by the formula -[S1]c -[Q1-[S2]d ]d~-[Q2 -[S3]e~]e~ -[Q3 - [S4]f ]f -S5-P, which is described herein.

Claims (93)

We claim:
1. A thermally reversible photochromic compound adapted to have at least a first state and a second state, wherein the thermally reversible photochromic compound has an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD.
2. The thermally reversible photochromic compound of claim 1 wherein the first state is an activated state, and the thermally reversible photochromic compound has an average absorption ratio greater than 2.3 in the activated state as determined according to CELL
METHOD.
3. The thermally reversible photochromic compound of claim 2 wherein the thermally reversible, photochromic compound has an average absorption ratio ranging from 2.5 to 50 in the activated state as determined according to CELL METHOD.
4. The thermally reversible photochromic compound of claim 2 wherein the thermally reversible photochromic compound has an average absorption ratio ranging from 3 to 30 in the activated state as determined according to CELL METHOD.
5. The thermally reversible photochromic compound of claim 2 wherein the thermally reversible photochromic compound has an average absorption ranging from 4. to 20 in the activated state as determined according to CELL METHOD.
6. A thermally reversible photochromic compound that is free of oxazines adapted to have at least a first state and a second state, wherein the thermally reversible photochromic compound has an average absorption ratio of at least 1.5 in at least one state as determined according to CELL METHOD.
7. The thermally reversible photochromic compound of claim 6 wherein the thermally reversible photochromic compound has an average absorption ratio ranging from 1.5 to 50.
8. A photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide;
and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c-[Q1-[S2]d]d'-[S3]e]e'-[Q3-[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T
is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;

provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 3.
9. A photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c-[Q1-[S2]d]d'-[Q2-[S3]e]e'-[Q3-[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C16 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(S) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S6 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
10. The photochromic compound of claim 9, wherein at least one of Q1, Q2, and Q3 is a unsubstituted or a substituted heterocyclic group chosen from: isosorbitol, dibenzofuro, dibenzothieno, benzofuro, benzothieno, thieno, furo, dioxino, carbazolo, anthranilyl, azepinyl, benzoxazolyl, diazepinyl, dioazlyl, imidazolidinyl, imidazolyl, imidazolinyl, indazolyl, indoleninyl, indolinyl, indolizinyl, indolyl, indoxazinyl, isobenzazolyl, isoindolyl, isooxazolyl, isooxazyl, isopyrroyl, isoquinolyl, isothiazolyl, morpholino, morpholinyl, oxadiazolyl, oxathiazolyl, oxathiazyl, oxathiolyl, oxatriazolyl, oxazolyl, piperazinyl, piperazyl, piperidyl, purinyl, pyranopyrrolyl, pyrazinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, pyrazyl, pyridazinyl, pyridazyl, pyridyl, pyrimidinyl, pyrimidyl, pyridenyl, pyrrolidinyl, pyrrolinyl, pyrroyl, quinolizinyl, quinuclidinyl, quinolyl, thiazolyl, triazolyl, triazyl, N-arylpiperazino, aziridino, arylpiperidino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, unsubstituted, mono- or di- substituted C4-C18 spirobicyclic amines, and unsubstituted, mono- or di- substituted C4-C18 spirotricyclic amines.
11. The photochromic compound of claim 9, wherein at least one of Q1, Q2, and Q3 is a unsubstituted or a substituted alicyclic group chosen from: cyclohexyl, cyclopropyl, norbornenyl, decalinyl, adamantanyl, bicyclooctane, per-hydrofluorene, and cubanyl.
12. The photochromic compound of claim 9, further comprising at least one R1 group attached to the at least one photochromic group, wherein each R1 group is independently chosen for each occurrence from:
(a) hydrogen, C1-C12 alkyl, C2-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C12 alkyl and C1-C12 alkoxy;

(b) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C7 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C4 alkyl substituted phenylene, mono-or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material;
(c) -CH(CN)2 and -CH(COOX1)2, wherein X1 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C12)alkyl that is mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(d) -CH(X2)(X3), wherein:
(i) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy; and (ii) X3 is chosen from at least one of -COOX1, -COX4, -COX4, and -CH2OX5, wherein:
(A) X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C12 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C12alkyl or C1-C12 alkoxy; and (B) X5 is chosen from a lengthening agent L, hydrogen, -C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(e) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, and fluorenyl; wherein each substituent is independently chosen for each occurrence from:
(i) a lengthening agent L;
(ii) -C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12alkyl or C1-C12 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(iii) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12alkoxy;
(iv) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di- (C1-C12)alkylaryl(C1-C12)alkyl, mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12alkyl;
(v) C1-C12 alkoxy, C3-C7 cycloalkoxy; cycloalkyloxy(C1-C12)alkoxy; aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di- (C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di- (C1-C12)alkyoxyaryl(C1-C12)alkoxy;
(vi) amido, amino, mono- or di-alkylamino, diarylamino, piperazino, N-(C1-C12)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(iii) -OX7 or -N(X7)2, wherein X7 is chosen from:
(A) a lengthening agent L, hydrogen, C1-C12 alkyl, C1-C12 aryl, phenyl(C1-C12)alkyl, mono(C1-C12)alkyl substituted phenyl(C1-C12)alkyl, mono(C1-C12)alkoxy substituted phenyl(C1-C12)alkyl; C1-C12 alkoxy(C1-C12)alkyl; C3-C7 cycloalkyl; mono(C1-C12)alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C12 alkyl, and C1-C12 alkoxy;
(B) -CH(X8)X9, wherein X8 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl; and X9 is chosen from a lengthening agent L, -CN, -CF3, or -COOX10, wherein X10 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl;
(C) -C(O)X6; or (D) tri(C1-C12)alkylsilyl, tri(C1-C12)alkoxysilyl, di(C1-C12)alkyl(C1-C12alkoxy)silyl, or di(C1-C12)alkoxy(C1-C12 alkyl)silyl;
(viii) SX11, wherein X11 is chosen from a lengthening agent L, C1-C12alkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C12 alkyl, C1-C12alkoxy, or halogen;
(ix) a nitrogen containing ring represented by Formula i:
wherein (A) n is an integer chosen from 0, 1, 2, and 3, provided that if n is 0, U' is U, and each U is independently chosen for each occurrence from -CH2-, -CH(X12)-2, -C(X12)2-, -CH(X13)2-, -C(X13)2-, and -C(X12)(X13)-, wherein X12 is chosen from a lengthening agent L represented by Formula I above and C1-C12 alkyl, and X13 is chosen from a lengthening agent L represented by Formula I above, phenyl and naphthyl, and (B) U' is chosen from U, -O-, -S-, -S(O)-, -NH-,-N(X12)- or-N(X13)-, and m is an integer chosen from 1, 2, and 3, and (x) a group represented by Formula ii or iii:
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 5 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(f) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, phenyl, hydroxy, amino or halogen;

(g) a group represented by Formula iv or v:
wherein (i) V' is independently chosen in each formula from -O-, -CH-, C1-C6 alkylene, and C3-C7 cycloalkylene, (ii) V is independently chosen in each formula from -O- or-N(X21)-, wherein X21 is from a lengthening agent L represented by Formula I above, hydrogen, C1-C12 alkyl, and C2-C12 acyl, provided that if V is -N(X21)-, V' is -CH2-, (iii) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (iv) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, hydroxy and halogen;
(h) a group represented by Formula vi:
(i) X22 is chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (ii) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C12 alkyl, C1-C12 alkoxy, and halogen;
(i) -C(O)X24, wherein X24 is chosen from a lengthening agent L, hydroxy, C1-alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C12 alkyl or C1-C12alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C12 alkyl, phenyl, benzyl, and naphthyl;
(j) -OX7 and -N(X7)2;
(k) -SX11;
(l) the nitrogen containing ring represented by Formula i;
(m) the group represented by one of Formula ii or iii; or (n) immediately adjacent R1 groups together form at a group represented by Formula vii, viii, or ix:

wherein (i) W and W' are independently chosen for each occurrence from -O-, -N(X7)-, -C(X14)-, -C(X17)-, (ii) X14, X15 and X17 are as set forth above, and (iii) q is an integer chosen from 0, 1, 2, 3, and 4.
13. The photochromic compound of claim 9 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
14. The photochromic compound of claim 9 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 3 to 30 in an activated state as determined according to CELL METHOD.
15. The photochromic compound of claim 9 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 4 to 20 in an activated state as determined according to CELL METHOD.
16. The photochromic compound of claim 9 wherein the at least one photochromic group is a photochromic pyran group chosen from benzopyrans, naphthopyrans, phenanthropyrans, quinopyrans, fluoroanthenopyrans, and spiropyrans.
17. The photochromic compound of claim 16 wherein the photochromic pyran group is a napththopyran group chosen from naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, indeno-fused naphthopyrans, and heterocyclic-fused naphthopyrans.
18. The photochromic compound of claim 16 wherein the photochromic pyran group is a spiropyran group chosen from spiro-9-fluoreno[1,2-b]pyrans, spiro(benzindoline)naphthopyrans, spiro(indoline)benzopyrans, spiro(indoline)naphthopyrans, spiro(indoline)quinopyrans and spiro(indoline)pyrans.
19. The photochromic compound of claim 9 wherein the at least one photochromic group is a photochromic oxazine group chosen from benzoxazines, naphthoxazines, and spiro-oxazines.
20. The photochromic compound of claim 19 wherein photochromic oxazine group is a spiro-oxazine group chosen form, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(benzindoline)pyridobenzoxazines, spiro(benzindoline)naphthoxazines, spiro(indoline)benzoxazines, spiro(indoline)fluoranthenoxazine, and spiro(indoline)quinoxazine.
21. The photochromic compound of claim 9 wherein the at least one photochromic group is chosen from indeno-fused naphthopyrans, naphtho[1, 2-b]pyrans, naphtho[2,1-b]pyrans, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazine, and spiro(indoline)quinoxazine.
22. The photochromic compound of claim 9 wherein at least one L comprises a main-chain or side-chain liquid crystal polymer.
23. The photochromic compound of claim 9 wherein at least one L comprises a liquid crystal mesogen.
24. A photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide;
and (b) at least one lengthening agent attached to the at least one photochromic group, wherein the at least one lengthening agent is chosen from:
(1) 4-[4-(4-butyl-cyclohexyl)-phenyl]-cyclohexyloxy;
(2) 4"-butyl-[1,1';4',1"]tercyclohexan-4-yloxy;
(3) 4-[4-(4-butyl-phenyl)-cyclohexyloxycarbonyl]-phenoxy;
(4) 4'-(4-butyl-benzoyloxy)-biphenyl-4-carbonyloxy;
(5) 4-(4-pentyl-phenylazo)-phenylcarbamoyl;
(6) 4-(4-dimethylamino-phenylazo)-phenylcarbamoyl;
(7) {4-[5-(4-propyl-benzoyloxy)-pyrimidin-2-yl]-phenyl} ester;
(8) {4-[2-(4'-methyl-biphenyl-4-carbonyloxy)-1,2-diphenyl-ethoxycarbonyl]-phenyl} ester;
(9) [4-(1,2-diphenyl-2-{3-[4-(4-propyl-benzoyloxy)-phenyl]-acryloyloxy}-ethoxycarbonyl)-phenyl] ester;

(10) {4-[4-(4-{4-[3-(6-{4-[4-(4-nonyl-benzoyloxy)-phenoxycarbonyl]-phenoxy}-hexyloxycarbonyl)-propionyloxy]-benzoyloxy}-benzoyloxy)-phenyl]-piperazin-1-yl;
(11) {4-[4-(4-{4-[4-(4-nonyl-benzoyloxy)-benzoyloxy]-benzoyloxy}-benzoyloxy)-phenyl]-piperazin-1-yl};
(12) 4-(4'-propyl-biphenyl-4-ylethynyl)-phenyl;
(13) 4-(4-fluoro-phenoxycarbonyloxy)-piperidin-1-yl;
(14) 2-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-indan-5-yl;
(15) 4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl;
(16) 4-(biphenyl-4-carbonyloxy)-piperidin-1-yl;
(17) 4-(naphthalene-2-carbonyloxy)-piperidin-1-yl;
(18) 4-hydroxy-piperidin-1-yl;
(19) 4-(4-phenylcarbamoyl-phenylcarbamoyl)-piperidin-1-yl;
(20) 4-(4-(4-phenylpiperidin-1-yl)-benzoyloxy)-piperidin-1-yl;
(21) 4-butyl-[1,1';4',1"]terphenyl-4-yl;
(22) 4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy;
(23) 4-(3-piperidin-4-yl-propyl)-piperidin-1-yl;
(24) 4-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-benzoyloxy}-phenoxycarbonyl)-phenoxymethyl;
(25) 4-[4-(4-cyclohexyl-phenylcarbamoyl)-benzyloxy]-piperidin-1-yl;
(26) 4-[4-(4-cyclohexyl-phenylcarbamoyl)-benzoyloxy]-piperidin-1-yl;
(27) N-{4-[(4-pentyl-benzylidene)-amino]-phenyl}-acetamidyl (28) 4-(3-piperidin-4-yl-propyl)-piperidin-1-yl;
(29) 4-(4-hexyloxy-benzoyloxy)-piperidin-1-yl;
(30) 4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl;
(31) 4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl;
(32) biphenyl-4,4'-dicarboxylic acid bis-[1-Name of PC]-piperidin-4-yl] ester (33) 4-(4-(9-(4-butylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undec-3-yl)phenyl)piperazin-1-yl;
(34) 4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl;

(35) 1-{4-[5-(4-butyl-phenyl)-[1,3]dioxan-2-yl]-phenyl}-4-methyl-piperazin-1-yl;
(36) 4-(7-(4-propylphenylcarbonyloxy)bicyclo[3.3.0]oct-2-yl)oxycarbonyl)phenyl;
and (37) 4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy.
25. A photochromic compound represented by Formula II:
wherein:
(a) A is chosen from naphtho, benzo, phenanthro, fluorantheno, antheno, quinolino, thieno, furo, indolo, indolino, indeno, benzofuro, benzothieno, thiopheno, indeno-fused naphtho, heterocyclic-fused naphtho, and heterocyclic-fused benzo;
(b) B and B' are each independently chosen from:
(i) hydrogen, C1-C12 alkyl, C2-C12 alkylidene, C2-C12alkylidyne, vinyl, C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C12 alkyl and C1-C12 alkoxy;
(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C7 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C4 alkyl substituted phenylene, mono-or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material;
(iii) -CH(CN)2 and -CH(COOX1)2, wherein X1 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C12)alkyl that is mono-substituted with C1-C12 alkyl or C1-C12alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12alkyl and C1-C12 alkoxy;
(iv) -CH(X2)(X3), wherein:
(A) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy; and (B) X3 is chosen from at least one of -COOX1, -COX1, -COX4, and -CH2OX5, wherein:
(1) X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C12 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C12 alkyl or C1-C12 alkoxy; and (2) X5 is chosen from a lengthening agent L, hydrogen, -C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(v) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each substituent is independently chosen for each occurrence from:
(A) a lengthening agent L;
(B) -C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(C) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(D) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di- (C1-C12)alkylaryl(C1-C12)alkyl, mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12)alkyl;

(E) C1-C12 alkoxy, C3-C7 cycloalkoxy, cycloalkyloxy(C1-C12)alkoxy, aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di- (C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkoxy;
(F) amido, amino, mono- or di-alkylamino, diarylamino, piperazino, N-(C1-C12)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(G) -OX7 or -N(X7)2, wherein X7 is chosen from:
(1) a lengthening agent L, hydrogen, C1-C12 alkyl, C1-C12 acyl, phenyl(C1-C12)alkyl, mono(C1-C12)alkyl substituted phenyl(C1-C12)alkyl, mono(C1-C12)alkoxy substituted phenyl(C1-C12)alkyl; C1-C12 alkoxy(C1-C12)alkyl; C3-C7 cycloalkyl; mono(C1-C12)alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C12 alkyl, and C1-C12 alkoxy;
(2) -CH(X8)X9, wherein X8 is chosen from a lengthening agent, hydrogen or C1-C12 alkyl; and X9 is chosen from a lengthening agent L, -CN,-CF3, or -COOX10, wherein X10 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl:
(3) -C(O)X6; or (4) tri(C1-C12)alkylsilyl, tri(C1-C12)alkoxysilyl, di(C1-C12)alkyl(C1-C12alkoxy)silyl, or di(C1-C12)alkoxy(C1-C12alkyl)silyl;
(H) -SX11, wherein X11 is chosen from a lengthening agent L, C1-C12 alkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C12 alkyl, C1-C12alkoxy, or halogen;
(I) a nitrogen containing ring represented by Formula i:
wherein (1) n is an integer chosen from 0, 1, 2, and 3, provided that if n is 0, U' is U, and each U is independently chosen for each occurrence from CH2-, -CH(X12)-, -C(X12)2-, -CH(X13)-, -C(X13)2-, and -C(X12)(X13)-, wherein X12 is chosen from a lengthening agent L represented by Formula I above and C1-C12 alkyl, and X13 is chosen from a lengthening agent L represented by Formula I above, phenyl and naphthyl, and (2) U' is chosen from U, -O-, -S-, -S(O)-, -NH-,-N(X12)- or -N(X13)-, and m is an integer chosen from 1, 2, and 3, and (J) a group represented by Formula ii or iii:
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(vi) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, phenyl, hydroxy, amino or halogen;
(vii) a group represented by Formula iv or v:
wherein (A) V' is independently chosen in each formula from -O-, -CH-, C1-C6 alkylene, and C3-C7 cycloalkylene, (B) V is independently chosen in each formula from -O- or-N(X21)-, wherein X21 is from a lengthening agent L represented by Formula I above, hydrogen, C1-C12 alkyl, and C2-C12 acyl, provided that if V is -N(X21)-, V' is -CH2-, (C) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (D) k is chosen from 0, 1, and 2, and each X2o is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, hydroxy and halogen;
(viii) a group represented by Formula vi:
wherein (A) X22 is chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (B) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C12 alkyl, C1-C12 alkoxy, and halogen; and (ix) B and B' together form fluoren-9-ylidene, mono- or di-substituted fluoren-ylidene, or a saturated C3-C12 spiro-monocyclic hydrocarbon ring, saturated C7-C12 spiro-bicyclic hydrocarbon rings, saturated C7-C12 spiro-tricyclic hydrocarbon rings; and (c) i is an integer chosen from 0 to the total available positions on A, and each R2 is independently chosen for each occurrence from:
(i) a group represented by B;
(ii) -C(O)X24, wherein X24 is chosen from a lengthening agent L, hydroxy, C1-alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C12 alkyl or C1-X12 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C12 alkyl, phenyl, benzyl, and naphthyl;
(iii) -OX7 and -N(X7)2;
(iv) -SX11;
(v) the nitrogen containing ring represented by Formula i;
(vi) the group represented by Formula ii or iii;
(vii) immediately adjacent R2 groups together form at a group represented by Formula vii, viii, or ix:
wherein (A) W and W' are independently chosen for each occurrence from -O-, -N(X7)-, -C(X14)-, -C(X17)-, (B) X14, X15 and X17, and (C) q is an integer chosen from 0, 1, 2, 3, and 4;
(viii) a lengthening agent L;
provided that the photochromic compound comprises at least one lengthening agent L
and each lengthening agent L is independently chosen for each occurrence from a compound represented by Formula I:
-[S1]c-[Q1-[S2]d]d'-[Q2-[S3]e]e'-[Q3-[S4]f]f'-S5-P I
wherein:
(a) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from:
a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(b) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(i) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(ii) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (iii) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(c) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (d) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 2.
26. The photochromic compound of claim 25 wherein A is naphtho, and the photochromic compound is represented by Formula III:
wherein at least one of B, B' or at least one R2 comprises a lengthening agent L.
27. The photochromic compound of claim 26 wherein the photochromic compound is represented by Formula IV:

wherein:
(a) at least one of an R2 substituent in the 6-position, an R2 substituent in the 8-position, B or B' comprises a lengthening agent L;
(b) the R2 substituent in the 6-position together with the R2 substituent in the 5-position forms a group represented by one of Formula x to Formula xiv:
wherein K is chosen from -O-, -S-, -N(X7)-; and an unsubstituted C or a C
substituted with alkyl, hydroxy, alkoxy, oxo, or aryl; K' is -C-,-O-, or -N(X7)-; K" is chosen from -O- or -N(X7)-; X25 is a group represented by R2; X26 can be chosen from hydrogen, alkyl, aryl, or two adjacent X26 together form benzo or naphtho;
and each X27 is chosen from alkyl and aryl or together are oxo; provided that at least one of: the R2 substituent in the 8-position, X25, K, K', K", B or B' comprises a lengthening agent L; or (c) the R2 substituent in the 6-position together with an R2 substituent in the 7-position from an aromatic group chosen from benzeno and naphtho, provided that at least one of an R2 substituent in the 8-position, B or B' comprises a lengthening agent L.
119 23. The photochromic compound of claim 27, wherein an R2 substituent in the 5-position and an R2 substituent in the 6-position together form an indeno group, and photochromic compound is represented by Formula V:
wherein wherein K is chosen from -O-, -S-, -N(X7)-; and an unsubstituted C or a C
substituted with alkyl, hydroxy, alkoxy, oxo, or aryl, and at least one of an R2 substituent in the 11-position, an R2 substituent in the 7-position, or K comprises a lengthening agent L.
29. The photochromic compound of claim 25 wherein A, is naphtho, and the photochromic compound is represented by Formula VI:
wherein at least one of B, B' or at least one R2 comprises a lengthening agent L.
30. The photochromic compound of claim 29 wherein the photochromic compound is represented by Formula VII:
wherein at least one of an R2 substituent in the 6-position or an R2 substituent in the 7-position comprises a lengthening agent L.
31. The photochromic compound of claim 25 wherein A is benzo, and the photochromic compound is represented by Formula VIII:
wherein at least one of B, B' or at least one R2 comprises a lengthening agent L.
32. The photochromic compound of claim 31 wherein the photochromic compound is represented by Formula IX:
wherein:
(a) at least one of: an R2 substituent in the 5-position, an R2 substituent in the 7-position, B or B' comprises a lengthening agent L; or (b) at least one of: the R2 substituent in the 5-position or the R2 substituent in the 7-position, together with an immediately adjacent R2 substituent, forms a group represented by at least one of Formula x to xiv:

wherein K is chosen from -O-, -S-, -N(X7)-; and an unsubstituted C or a C
substituted with alkyl, hydroxy, alkoxy, oxo, or aryl; K' is -C-,-O-, or -N(X7)-; K" is chosen from -O- or -N(X7)-; X25 is a group represented by R2; X26 can be chosen from hydrogen, alkyl, aryl, or two adjacent X~6 together form benzo or naphtho;
and each X27 is chosen from alkyl and aryl or together are oxo; provided that at least one of: the R2 substituent in the 3-position, X25, K, K', K", B or B' comprises a lengthening agent L.
33. The photochromic compound of claim 25 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
34. The photochromic compound of claim 25 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 3 to 30 in an activated state as determined according to CELL METHOD.
35. The photochromic compound of claim 25 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 4 to 20 in an activated state as determined according to CELL METHOD.
36. A photochromic compound represented by Formula XII:

wherein:
(a) A is chosen from naphtho, benzo, phenanthro, fluorantheno, antheno, quinolino, thieno, furo, indolo, indolino, indeno, benzofuro, benzothieno, thiopheno, indeno-fused naphtho, heterocyclic-fused naphtho, and heterocyclic-fused benzo;
(b) Y is C or N;
(c) SP is a spiro-group chosen from indolino and benzindolino; and (d) i is an integer chosen from 0 to the total number of available positions on A, r is an integer chosen from 0 to the total number available positions on SP, provided that the sum of i + r is at least one, and each R3 is independently chosen for each occurrence from:
(i) hydrogen, C1-C12 alkyl, C2-C12 alkylidene, C2-C12 alkylidyne, vinyl, C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C12 alkyl and C1-C12 alkoxy;
(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C7 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C4 alkyl substituted phenylene, mono-or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material;
(iii) -CH(CN)2 and -CH(COOX1)2, wherein X1 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C12)alkyl that is mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(iv) -CH(X2)(X3), wherein:
(A) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy; and (B) X3 is chosen from at least one of -COOX1, -COX1, -COX4, and -CH2OX5, wherein:
(1) X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C12 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C12 alkyl or C1-C12 alkoxy; and (2) X5 is chosen from a lengthening agent L, hydrogen, -C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(v) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each substituent is independently chosen for each occurrence from:
(A) a lengthening agent L;
(B) -C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(C) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(D) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di- (C1-C12)alkylaryl(C1-C12)alkyl, mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12)alkyl;
(E) C1-C12 alkoxy, C3-C7 cycloalkoxy, cycloalkyloxy(C1-C12)alkoxy, aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di- (C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkoxy;

(F) amido, amino, mono- or di-alkylamino, diarylamino, piperazino, N-(C1-C12)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(G) -OX7 and -N(X7)2, wherein X7 is chosen from:
(1) a lengthening agent L, hydrogen, C1-C12 alkyl, C1-C12 aryl, phenyl(C1-C12 )alkyl, mono(C1-C12 )akyl substituted phenyl(C1-C12 )alkyl, mono(C1-C12 )alkoxy substituted phenyl(C1-C12 )alkyl; C1-C12 alkoxy(C1-C12 )alkyl; C3-C7 cycloalkyl; mono(C1-C12 )alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C12 alkyl, and C1-C12 alkoxy;
(2) -CH(X8)X9, wherein X7 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl; and X9 is chosen from a lengthening agent L, -CN, -CF3, or -COOX10, wherein X1o is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl;
(3) -C(O)X6;
(4) tri(C1-C12)alkylsilyl, tri(C1-C12)alkoxysilyl, di(C1-C12)alkyl(C1-C12alkoxy)silyl, or di(C1-C12)alkoxy(C1-C12 alkyl)silyl;
(H) -SX11, wherein X11 is chosen from a lengthening agent L, C1-C12 alkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(I) a nitrogen containing ring represented by Formula i:
wherein (1) n is an integer chosen from 0, 1, 2, and 3, provided that if n is 0, U' is U, and each U is independently chosen for each occurrence from CH2-, -CH(X12)-, -(X12)2-, -CH(X13)-, -C(X13)2-, and -C(X12)(X13)-, wherein X12 is chosen from a lengthening agent L represented by Formula I above and C1-C12 alkyl, and X13 is chosen from a lengthening agent L represented by Formula I above, phenyl and naphthyl, and (2) U' is chosen from U, -O-, -S-, -S(O)-, -NH-,-N(X12)- or-N(X13)-, and m is an integer chosen from 1, 2, and 3, and (J) a group represented by Formula ii or iii:
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(vi) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, phenyl, hydroxy, amino or halogen;
(vii) a group represented by Formula iv or v:
wherein (A) V' is independently chosen in each formula from -O-, -CH-, C1-C6 alkylene, and C3-C7 cycloalkylene, (B) V is independently chosen in each formula from -O- or -N(X21)-, wherein X21 is from a lengthening agent L represented by Formula I above, hydrogen, C1-C12 alkyl, and C2-C12 acyl, provided that if V is -N(X21)-, V' is -CH2-, (C) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (D) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, hydroxy and halogen;

(viii) a group represented by Formula vi:
wherein (A) X22 is chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (B) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C1~ alkyl, C1-C12 alkoxy, and halogen;
(ix) -C(O)X24, wherein X24 is chosen from a lengthening agent L, hydroxy, C1-alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C12 alkyl, phenyl, benzyl, and naphthyl;
(x) -OX7 and -N(X7)2;
(xi) -SX11;
(xii) the nitrogen containing ring represented by Formula i;
(xiii) the group represented by Formula ii or iii; or (xiv) immediately adjacent R3 groups together form at a group represented by Formula vii, viii, or ix:
wherein (A) W and W' are independently chosen for each occurrence from -O-, -N(X7)-, -C(X14)-, -C(X17)-, (B) X14, X15 and X17, and (C) q is an integer chosen from 0, 1, 2, 3, and 4; and (xv) a lengthening agent L;
provided that the photochromic compound comprises at least one lengthening agent L
and each lengthening agent L is independently chosen for each occurrence from a compound represented by Formula I:
-[S1]c-[Q1-[S2]d]d'-[Q2-[S3]e]e'-[Q3-[S4]f]f'-S5-P I
wherein:

(a) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from:
a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group represented by one of the following formulae:-M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(b) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(i) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(ii) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (iii) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(c) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein at least one substituent is chosen from an alkyl having an optically active group, an alkoxy, amino, cycloalkyl, alkylalkoxy, a fluoroalkyl, a cyanoalkyl, a cyanoalkoxy, and mixtures thereof; and (d) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 2.
37. The photochromic compound of claim 36 wherein SP is indolino, and the photochromic compound comprises is represented by Formula XIII:
wherein:
(a) each R" is independently chosen for each occurrence from hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, arylalkyl, or together form cycloalkyl that is substituted or unsubstituted;
(b) R"' is chosen from an alkyl, aryl or arylalkyl group that is unsubstituted or substituted with:
(i) -CH(CN)2 or CH(COOX1)2, (ii) -CH(X2)(X3), (iii) -C(O)X24, or (iv) halogen, hydroxy, ester, or amine; and (c) at least one of i and r is at least 1, and at least one R3 comprises a lengthening agent L.
38. The photochromic compound of claim 36 wherein the photochromic compound is represented by Formula XIV:
wherein at least one R3 comprises a lengthening agent L.
39. The photochromic compound of claim 38 wherein the photochromic compound is represented by Formula XV:
wherein at least one R3 comprises a lengthening agent L.
40. The photochromic compound of claim 36 wherein A is naphtho, Y is N, and the photochromic compound is represented by Formula XVI or VII:
wherein, for each formula, at least one of i and r is at least 1, and at least one R3 comprises a lengthening agent L.
41. The photochromic compound of claim 40 wherein the photochromic compound is represented by Formula XVIII or XIX:
wherein, for each formula, at least one R3 comprises a lengthening agent L.
42. The photochromic compound of claim 36 wherein A is benzo, Y is N, and the photochromic compound is represented by Formula XX:
wherein at least one of i or r is at least 1, and at least one R3 comprises a lengthening agent L.
43. The photochromic compound of claim 42 wherein i is 1 and the photochromic compound is represented by Formula XXI:
wherein at least one R3 comprises a lengthening agent L.
44. The photochromic compound of claim 36 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
45. The photochromic compound of claim 36 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 3 to 30 in an activated state as determined according to CELL METHOD.
46. The photochromic compound of claim 36 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 4 to 20 in an activated state as determined according to CELL METHOD.
47. A photochromic compound represented by one of Formula XXII or Formula XYV:
wherein for each formula:
(a) A is chosen from naphtho, benzo, phenanthro, fluorantheno, antheno, quinolino, thieno, furo, indolo, indolino, indeno, benzofuro, benzothieno, thiopheno, indeno-fused naphtho, heterocyclic-fused naphtho, and heterocyclic-fused benzo;
(b) J is a spiro-alicyclic ring;
(c) each D is independently chosen from O, N(Z), C(X4), C(CN)2,wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl;
(d) G is group chosen from alkyl, cycloalkyl, and aryl, which can be unsubstituted or substituted with at least one substituent R4;
(e) E is -O- or -N(R5)-, wherein R5 is chosen from:

(i) hydrogen, C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, vinyl, C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C12 alkyl and C1-C12 alkoxy;
(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C7 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C4 alkyl substituted phenylene, mono-or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C10)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material;
(iii) -CH(CN)2 and -CH(COOX1)2, wherein X1 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C12)alkyl that is mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(iv) -CH(X2)(X3), wherein:
(A) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy; and (B) X3 is chosen from at least one of -COOX1, -COX1, -COX4, and -CH2OX5, wherein:
(1) X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C12 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C12 alkyl or C1-C12 alkoxy; and (2) X5 is chosen from a lengthening agent L, hydrogen, -C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(v) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each substituent is independently chosen for each occurrence from:
(A) a lengthening agent L;
(B) -C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(C) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(D) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di- (C1-C12)alkylaryl(C1-C12)alkyl, mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12)alkyl;
(E) C1-C12 alkoxy, C3-C7 cycloalkoxy, cycloalkyloxy(C1-C12)alkoxy, aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di- (C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkoxy;
(F) amido, amino, mono- or di-alkylamino, diarylamino, piperazino, N-(C1-C12)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(G) -OX7 and -N(X7)2, wherein X7 is chosen from:
(1) a lengthening agent L, hydrogen, C1-C12 alkyl, C1-C12 acyl, phenyl(C1-C12)alkyl, mono(C1-C12)akyl substituted phenyl(C1-C12)alkyl, mono(C1-C12)alkoxy substituted phenyl(C1-C12)alkyl; C1-C12 alkoxy(C1-C12)alkyl; C3-C7 cycloalkyl; mono(C1-C12)alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C12 alkyl, and C1-C12 alkoxy;
(2) -CH(X8)X9, wherein X8 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl; and X9 is chosen from a lengthening agent L, -CN, -CF3, or -COOX10, wherein X10 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl;
(3) -C(O)X6; or (4) tri(C1-C12)alkylsilyl, tri(C1-C12)alkoxysilyl, di(C1-C12)alkyl(C1-C12alkoxy)silyl, or di(C1-C12)alkoxy(C1-C12 alkyl)silyl;
(H) -SX11, wherein X11 is chosen from a lengthening agent L, C1-C12 alkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C12 alkyl, C1-C12alkoxy, or halogen;
(I) a nitrogen containing ring represented by Formula i:
wherein (1) n is an integer chosen from 0, 1, 2, and 3, provided that if n is 0, U' is U, and each U is independently chosen for each occurrence from -CH2-, -CH(X12)-, -(X12)2-, -CH(X13)-, -C(X13)2-, and -C(X12)(X13)-, wherein X12 is chosen from a lengthening agent L represented by Formula I above and C1-C12 alkyl, and X13 is chosen from a lengthening agent L represented by Formula I above, phenyl and naphthyl, and (2) U' is chosen from U, -O-, -S-, -S(O)-, -NH-,-N(X12)- or-N(X13)-, and m is an integer chosen from 1, 2, and 3, and (J) a group represented by one of Formula ii or iii:
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(vi) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, phenyl, hydroxy, amino or halogen;
(vii) a group represented by one of Formula iv or v:

wherein (A) V' is independently chosen in each formula from -O-, -CH-, C1-C6 alkylene, and C3-C7 cycloalkylene, (B) V is independently chosen in each formula from -O- or-N(X21)-, wherein X21 is from a lengthening agent L represented by Formula I above, hydrogen, C1-C12 alkyl, and C2-C12 acyl, provided that if V is -N(X21)-, V' is -CH2-, (C) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (D) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, hydroxy and halogen;
(viii) a group represented by Formula vi:

wherein (A) X22 is chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (B) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C12 alkyl, C1-C12 alkoxy, and halogen; and (ix) a lengthening agent L; and (f) i is an integer chosen from 0 to the total available positions on A, and each R4 is independently chosen for each occurrence from:
(i) a group represented by R5;
(ii) -C(O)X24, wherein X24 is chosen from a lengthening agent L, hydroxy, C1-alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C12 alkyl, phenyl, benzyl, and naphthyl;
(iii) -OX7 and -N(X7)2;
(iv) -SX11;
(v) the nitrogen containing ring represented by Formula i;
(vi) the group represented by one of Formula ii or iii; or (vii) immediately adjacent R4 groups together form at a group represented by one of Formula vii, viii, or ix:
wherein (A) W and W' are independently chosen for each occurrence from -O-, -N(X7)-, -C(X14)-, -C(X17)-, (B) X14, X15 and X17, and (C) q is an integer chosen from 0, 1, 2, 3, and 4;
provided that the photochromic compound comprises at least one lengthening agent L
and each lengthening agent L is independently chosen for each occurrence from a compound represented by Formula I:
-[S1]c-[Q1-[S2]d]d'-[Q2-[S3]e]e'-[Q3-[S4]f]f'-S5-P I
wherein:
(a) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from:
a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group represented by one of the following formulae:-M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(b) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(i) -(CH2)g , -(CF2)n-, -Si(CH2)g-, -(Si[(CH3)2]O)n-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(ii) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (iii) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(c) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (d) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d'+ e'+f'is at least 2.
48. The photochromic compound of 47 wherein A is thiophene, E is -N(R5)-, each D is O, and the photochromic compound is represented by Formula XXIII:
wherein at least one of G, R5 or at least one R4 comprises a lengthening agent L.
49. The photochromic compound of claim 47 wherein the photochromic compound is represented by Formula XXIV:
wherein at least one of R4, R5 or G comprises a lengthening agent L.
50. The photochromic compound of claim 47 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
51. The photochromic compound of claim 47 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 3 to 30 in an activated state as determined according to CELL METHOD.
52. The photochromic compound of claim 47 wherein the photochromic compound is a photochromic-dichroic compound having an average absorption ratio ranging from 4 to 20 in an activated state as determined according to CELL METHOD.
53. A photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide;
and (b) at least one lengthening agent L2 attached to the at least one photochromic group, the at least one lengthening agent L2 represented by:

-[S]s'-P' wherein:
(i) P' is a group chosen from steroid radicals, terpenoid radicals, alkaloid radicals, and liquid crystal mesogens; and (ii) s'is chosen from 0 to 20, and each S is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g -, -(CF2)n-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C=C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other.
54. A non-thermally reversible photochromic compound represented by one of Formula X and Formula XI:
wherein:

(a) A is chosen from naphtho, benzo, phenanthro, fluorantheno, antheno, quinolino, thieno, furo, indolo, indolino, indeno, benzofuro, benzothieno, thiopheno, indeno-fused naphtho, heterocyclic-fused naphtho, and heterocyclic-fused benzo;
(b) AA is a group represented by one of Formula xv and xvi:
wherein X29 is independently chosen from each occurrence form -C(R")(R")-,-O-, -S-, and -N(R"')-, wherein R" is independently chosen for each occurrence from hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, arylalkyl, or together form cycloalkyl that is substituted or unsubstituted; R"' is independently chosen for each occurrence from an alkyl, aryl or arylalkyl group that is unsubstituted or substituted with at least one of:
(i) -CH(CN)2 or-CH(COOX1)2 wherein X1 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C12)alkyl that is mono-substituted with C1-C12 alkyl or C1-C12 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(ii) -CH(X2)(X3) wherein (A) X2 is chosen from at least one of a lengthening agent L, hydrogen, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy; and (B) X3 is chosen from at least one of -COOX1, -COX1, -COX4, and -CH2OX5, wherein:
(1) X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di- substituted with C1-C12 alkyl, and an unsubstituted, mono or di- substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C12 alkyl or C1-C12 alkoxy; and (2) X5 is chosen from a lengthening agent L, hydrogen, -C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C12 alkyl and C1-C12 alkoxy;
(iii) -C(O)X24; wherein X24 is chosen from a lengthening agent L, hydroxy, C1-alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C12 alkyl or C1-C12alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C12 alkyl, phenyl, benzyl, and naphthyl; or (iv) halogen, hydroxy, ester, or amine;
(c) Y' is chosen from: -(Y1)C=C(Y2)-, -O-,-S-,-S(O)(O)-, and -N(X7)-, wherein Y1 and Y2 together form benzo, naphtho, phenanthro, furo, thieno, benzofuro, benzothieno and indolo, and X7 is chosen from:
(i) a lengthening agent L, hydrogen, C1-C12alkyl, C1-C12acyl, phenyl(C1-C12 )alkyl, mono(C1-C12)akyl substituted phenyl(C1-C12)alkyl, mono(C1-C12 )alkoxy substituted phenyl(C1-C12)alkyl; C1-C12 alkoxy(C1-C12)alkyl; C3-C7 cycloalkyl; mono(C1-C12)alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C12 alkyl, and C1-C12 alkoxy;
(ii) -CH(X8)X9, wherein X8 is chosen from a lengthening agent L, hydrogen or C12 alkyl; and X9 is chosen from a lengthening agent L, -CN, -CF3, or -COOX10, wherein X10 is chosen from a lengthening agent L, hydrogen or C1-C12 alkyl;
(iii) -C(O)X6, wherein X6 is chosen from at least one of: a lengthening agent L, hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;
(iv) tri(C1-C12)alkylsilyl, tri(C1-C12)alkoxysilyl, di(C1-C12)alkyl(C1-C12alkoxy)silyl, or di(C1-C12)alkoxy(C1-C12 alkyl)silyl;
(d) B is chosen from:
(i) hydrogen, C1-C12 alkyl, C2-C12 alkylidene, C2-C12alkylidyne, vinyl, C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C12 alkyl and C1-C12 alkoxy;
(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C7 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C4 alkyl substituted phenylene, mono-or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono-or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material;
(iii) -CH(CN)2 and -CH(COOX1)2;
(iv) -CH(X2)(X3);
(v) an unsubstituted, mono-, di-, or tri- substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each substituent is independently chosen for each occurrence from:
(A) a lengthening agent L;
(B) -C(O)X6;
(C) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12alkoxy;
(D) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di- (C1-C12)alkylaryl(C1-C12)alkyl, mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12)alkyl;
(E) C1-C12 alkoxy, C3-C7 cycloalkoxy, cycloalkyloxy(C1-C12)alkoxy, aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di- (C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di- (C1-C12)alkoxyaryl(C1-C12)alkoxy;
(F) amido, amino, mono- or di-alkylamino, diarylamino, piperidino, N-(C1-C12)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(G) -OX7 or -N(X7)2;
(H) -SX11, wherein X11 is chosen from a lengthening agent L, C1-C12 alkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(I) a nitrogen containing ring represented by Formula i:

wherein (1) n is an integer chosen from 0, 1, 2, and 3, provided that if n is 0, U' is U, and each U is independently chosen for each occurrence from -CH2-, -CH(X12)-, -C(X12)2-, -CH(X13)-, -C(X13)2-, and -C(X12)(X13)-, wherein X12 is chosen from a lengthening agent L represented by Formula I above and C1-C12 alkyl, and X13 is chosen from a lengthening agent L represented by Formula I above, phenyl and naphthyl, and (2) U' is chosen from U, -O-, -S-, -S(O)-, -NH-,-N(X12)- or-N(X13)-, and m is an integer chosen from 1, 2, and 3, and (J) a group represented by Formula ii or iii:
wherein X14, X15, and X16 are independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;
(vi) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, phenyl, hydroxy, amino or halogen;
(vii) a group represented by Formula iv or v:
(A) V' is independently chosen in each formula from -O-, -CH-, C1-C6 alkylene, and C3-C7 cycloalkylene, (B) V is independently chosen in each formula from -O- or-N(X21)-, wherein X21 is from a lengthening agent L represented by Formula I above, hydrogen, C1-C12 alkyl, and C2-C12 acyl, provided that if V is -N(X21)-, V' is -CH2-, (C) X18 and X19 are each independently chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (D) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, hydroxy and halogen; and (viii) a group represented by Formula vi:
wherein (A) X22 is chosen from a lengthening agent L, hydrogen and C1-C12 alkyl, and (B) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C12 alkyl, C1-C12 alkoxy, and halogen; and (e) i is an integer chosen from 0 to 4, and each R2 is independently chosen for each occurrence from:
(i) a group represented by B;
(ii) - C(O)X24;
(iii) -OX7 and -N(X7)2;
(iv) -SX11;
(v) the nitrogen containing ring represented by Formula i;
(vi) the group represented by Formula ii or iii;
(vii) immediately adjacent R2 groups together form at a group represented by Formula vii, viii, or ix:
wherein (A) W and W' are independently chosen for each occurrence from -O-, -N(X7)-, -C(X14)-, -C(X17)-, B14, X15 and X17, and (C) q is an integer chosen from 0, 1, 2, 3, and 4; and (viii) a lengthening agent L;
provided that the non-thermally reversible photochromic compound comprises at least one lengthening agent L and each lengthening agent L is independently chosen for each occurrence from a compound represented by Formula I:
-[S1]c-[Q1 -[S2]d]d' -[Q2 -[S3]e]e' -[Q3 -[S4]f]f -S5-P I
wherein:
(a) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from:
a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group represented by one of the following formulae:-M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(b) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(i) -(CH2)g , -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)n-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(ii) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (iii) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(c) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (d) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
55. A photochromic compound chosen form:
(a) 3-phenyl-3-(4-(4-piperidinopiperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(b) 3-phenyl-3-(4-(4-benzylpiperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(c) 3-phenyl-3-(4-(4-(3-piperidin-4-yl-propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]-naphtho[1,2-b]pyran;
(d) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran (e) 3-phenyl-3-(4-(4-phenylpiperazine)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;

(f) 3-phenyl-3-(4-(4-benzylpiperazine)phenyl)- 13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(g) 3-phenyl-3-(4-(4-hexyloxymethyl piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(h) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl) phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(i) 3-phenyl-3-(4-pyrrolidin-1-yl-phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(j) 3-phenyl-3-(4-pyrrolidin-1-yl-phenyl)-13,13-dimethyl-6-methoxy-7-([1,4']bipiperidinyl-1"-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(k) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-([1,4']bipiperidinyl-1'-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(l) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-benzylpiperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(m) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-(piperadin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(n) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(o) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(p) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexyloxy-benzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(q) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(r) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(s) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(t) 3-phenyl-3-(4-(4-pyrrolidinylphenyl)- 13,13-dimethyl-6-methoxy-7-(-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}indeno[2',3':3,4]naphtho[1,2-b]pyran;

(u) 3-phenyl-3-(4-(1-hydroxypiperidin-1-yl)-phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(v) 3-phenyl-3-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a] phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(w) 3-phenyl-3-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(x) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(y) 3-phenyl-3-(4-(4-(biphenyl-4-carbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-4-(4-(biphenyl-4-carbonyloxy)-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(z) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-[17-(1,5-dimefihyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl]-piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(aa) 3-phenyl-3-(4-(4-hexylbenzoyloxy)-piperadin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(bb) 3-phenyl-3-(4-(4-fluorobenzoyloxy)-piperadin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(cc) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-3-hydroxy-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(dd) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-hexylbenzoyloxy-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ee) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;

(ff) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl]-piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(gg) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-phenyl-piperazin-1-yl)-4-oxo-butanoyl)-piperazine-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(hh) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-fluorobenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ii) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-biphenylcarbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(jj) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(kk) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexyloxyphenylcarbonyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ll) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-(4-[17-(1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-phenyl)-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(mm) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)-phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(nn) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(oo) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(2-fluorobenzoyloxy)benzoyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(pp) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-fluorobenzoyloxy)benzoyloxy)-phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(qq) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;

(rr) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)-benzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(ss) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-hexylbenzoyloxy)-indeno[2',3':3,4] naphtho[1,2-b]pyran;
(tt) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(uu) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)benzoyloxy)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(w) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)- benzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ww) 3-phenyl-3-(4-(4-methoxyphenyl)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(3-phenylprop-2-ynoyloxy)phenyl)piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(xx) 3-phenyl-3-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-13,13-dimethyl-6-methoxy-7-(4-phenylpiperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(yy) 3-phenyl-3-(4-(4'-octyloxybiphenyl-4-carbonyloxy)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7-(4-(phenyl)-piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(zz) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7-(3-(4-hexylbenzoyloxyphenyl)piperazin-1-yl)-indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(aaa) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(bbb) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ccc) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,3, 9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(ddd) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl}-13,13-dimethyl-6-methoxy-indeno[2',3':3,4]naphtho[1,2-b]pyran-7-yl)-piperadin-1-yl)oxycarbonyl)phenyl)phenyl)cabonyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(eee) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl)-3-phenyl-7-methoxycarbonyl-3H-naphtho[2,1-b]pyran;
(fff) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-hydroxycarbonyl-3H-naphtho[2,1-b]pyran;
(ggg) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(4-phenyl-(phen-1-oxy)carbonyl)-3H-naphtho[2,1-b]pyran;
(hhh) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(N-(4-((4-dimethylamino)phenyl)diazenyl)phenyl)carbamoyl-3H-naphtho[2,1-b]pyran;
(iii) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzofuro[3',2':7,8]
benzo[b]pyran;
(jjj) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzothieno[3',2':7,8] benzo[b]pyran;
(kkk) 7-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}-2-phenyl-2-(4-pyrrolidin-1-yl-phenyl)-6-methoxycarbonyl-2H-benzo[b]pyran;
(lll) 2-phenyl-2-(4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-methoxycarbonyl-2H-naphtho[1,2-b]pyran;
(mmm) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-butyl-phenyl))carbamoyl-2H-naphtho[1,2-b]pyran;
(nnn) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(ooo) 1,3,3-trimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(ppp) 1,3,3-trimethyl-6'-(4-[N-(4-butylphenyl)carbamoyl]-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(qqq) 1,3,3-trimethyl-6'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(rrr) 1,3,3-trimethyl-6'-(4-(4-hydroxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];

(sss) 1,3,3,5,6-pentamethyl-7'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(ttt) 1,3-diethyl-3-methyl-5-methoxy-6'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(uuu) 1,3-diethyl-3-methyl-5-[4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy]-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(vvv) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(www) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-fluoantheno[1,2-b]pyran;
(xxx) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-11-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-2H-fluoantheno[1,2-b]pyran;
(yyy) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(zzz) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-7'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(aaaa) 1,3-diethyl-3-methyl-5-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(bbbb) 1-butyl-3-ethyl-3-methyl-5-methoxy-7-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(cccc) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-methoxycarbonyl-6-methyl-2H-9-(4-(4-propylphenyl)carbonyloxy)phenyl)(1,2-dihydro-9H-dioxolano[4',5':6,7] naphtho[1,2-b]pyran;
(dddd) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-(4-(4-propylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":6,7]][indeno[2',3':3,4]]naphtho[1,2-b]pyran;

(eeee) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-(4-(4-hexylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":5,6]][indeno[2',3':3,4]] naphtho[1,2-b]pyran;
(ffff) 4-(4-((4-cyclohexylidene-1-ethyl-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(gggg) 4-(4-((4-adamantan-2-ylidene-1-(4-(4-hexylphenyl)carbonyloxy)phenyl)-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(hhhh) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl (4-propyl)benzoate;
(iiii) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(jjjj) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,3,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(kkkk) 4-(4-methyl-5,7-dioxo-6-(4-(4-(4-propylphenyl)piperazinyl)phenyl)spiro[8,7a-dihydrothiapheno[4,5-f]isoindole-3,2'-adamentane]-2-yl)phenyl (4-propyl) phenyl benzoate;
(llll) N-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,3,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl -6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(mmmm) N-cyanomethyl-6,7-dihydro-2-(4-(4-(4-propylphenyl)piperazinyl)phenyl)-4 methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(nnnn) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1 yl)phenyl-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(oooo) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1 yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]thiophenedicarboxyimide-7,2 tricyclo[3.3.1.1] decane);
(pppp) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]furodicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);

(qqqq) N-cyanomethyl-6,7-dihydro-4-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(rrrr) N-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,3,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl -6,7-dihydro-2-(4-methoxyphenyl)phenyl-4-methylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(ssss) N-cyanomethyl-2-(4-(6-(4-butylphenyl)carbonyloxy-(4,3-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl -6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]
thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(tttt) 6,7-dihydro-N-methoxycarbonylmethyl-4-(4-(6-(4-butylphenyl)carbonyloxy-(4,3-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(uuuu) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-(4-(4-(4-(4-(6-(4-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)benzoyloxy)phen yl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(vvvv) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)benzoyloxy)phen yl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran; and (wwww) 3-phenyl-3-(4-pyrrolidinylphenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran.
56. A photochromic article comprising an organic host material and a photochromic amount of a thermally reversible photochromic compound connected to at least a portion of the organic host material, wherein the thermally reversible photochromic compound is adapted to have an first state, a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD.
57. A photochromic article comprising an organic host material and a photochromic amount of a photochromic compound connected to at least a portion of the organic host material, the photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide;
and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c -[Q1 -[S2]d]d' -[Q2 -[S3]e]e' -[Q3 -[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substitiuted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T
is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;

provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 3.
55. A photochromic article comprising an organic host material and a photochromic amount of a photochromic compound connected to at least a portion of the organic host material, the photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
- [S1]c -[Q1 -[S2]d]d' -[Q2 -[S3]e' -[Q3 -[S4]f'- S5 -P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T
is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstitufied, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
59. The photochromic article of claim 55 wherein the organic host material is chosen from polyacrylates, polymethacrylates, poly(C1 -C12) alkyl methacrylates, polyoxy(alkylene methacrylates), poly (alkoxylated phenol methacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), poly(vinylpyrrolidone), poly((meth)acrylamide), poly(dimethyl acrylamide), poly(hydroxyethyl methacrylate), poly((meth)acrylic acid), thermoplastic polycarbonates, polyesters, polyurethanes, polythiourethanes, poly(ethylene terephthalate), polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral and polymers of members of the group consisting of polyol(allyl carbonate)monomers, mono-functional acrylate monomers, mono-functional methacrylate monomers, polyfunctional acrylate monomers, polyfunctional methacrylate monomers, diethylene glycol dimethacrylate monomers, diisopropenyl benzene monomers, alkoxylated polyhydric alcohol monomers and diallylidene pentaerythritol monomers.
60. The photochromic article of claim 59 wherein the organic host material is a homopolymer or copolymer of monomer(s) chosen from acrylates, methacrylates, methyl methacrylate, ethylene glycol bis methacrylate, ethoxylated bisphenol A
dimethacrylate, vinyl acetate, vinylbutyral, urethane, thiourethane, diethylene glycol bis(allyl carbonate), diethylene glycol dimethacrylate, diisopropenyl benzene, and ethoxylated trimethylol propane triacrylate.
61. The photochromic article of claim 60 wherein said organic host material is an optical element.
62. The photochromic article of claim 61 wherein said optical element is an ophthalmic lens.
63. The photochromic article of claim 58 further comprising at least one other organic photochromic compound having at least one activated absorption maxima within the range of 300 nm to 1000 nm, inclusive.
64. A photochromic article comprising:
a substrate; and an at least partial coating of a coating composition connected to at least a portion of at least one surface of the substrate, said coating composition comprising a photochromic amount of a thermally reversible photochromic compound, wherein the thermally reversible photochromic compound is adapted to have an first state, a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD.
65. A photochromic article comprising:
a substrate; and an at least partial coating of a coating composition connected to at least a portion of at least one surface of the substrate, said coating composition comprising a photochromic amount of a photochromic compound, the photochromic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
- [S1]c -[Q1 -[S2]d]d' -[Q2 -[S3]e]e' -[Q3 -[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(S) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
66. The photochromic article of claim 65 wherein the at least partial coating is at least parfiially set.
67. The photochromic article of claim 65 wherein the coating composition is chosen from a polymeric coating composition, a paint, and an ink.
63. The photochromic article of claim 65 wherein the substrate is chosen from the group consisting of glass, masonry, textiles, ceramics, metals, wood, paper and polymeric organic materials.
69. The photochromic article of claim 65 further comprising at least one other organic photochromic compound having at least one activated absorption maxima with in the range of 300 nm to 1000 nm, inclusive.
70. An optical element comprising:
a substrate; and an at least partial coating connected to at least a portion of the substrate, the at least partial coating comprising at least one thermally reversible photochromic compound adapted to have an first state, a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD.
71. An optical element comprising:
a substrate; and an at least partial coating connected to at least a portion of the substrate, the at least partial coating comprising at least one photochromic compound, wherein the photochromic compound comprises:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c -[Q1 -[S2]d]d' -[Q2 -[S3]e]e' -[Q3 -[S4]f]f'- 5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(g) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC
and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 3.
72. An optical element comprising:
a substrate; and an at least partial coating connected to at least a portion of the substrate, the at least partial coating comprising at least one photochromic compound, wherein the photochromic compound comprises:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
- [S1]c-[Q1 -[S2]d'-[Q2 -[S3]e']e' -[Q3 -[S4]f-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:

(A) -(CH2)9 , -(CF2)h-, -Si(CH2)g, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
73. The optical element of claim 72 wherein the optical element is chosen from ophthalmic elements, display elements, windows, and mirrors.
74. The optical element of claim 72 wherein the optical element is an ophthalmic element and the substrate is an ophthalmic substrate chosen from corrective and non-corrective lenses, partially formed lenses, and lens blanks.
75. The optical element of claim 72 wherein the optical element is a display element chosen from screens, monitors, and security elements.
76. The optical element of claim 75 wherein the security elements are variable, linearly polarizing, optical security elements.
77. The optical element of claim 72 wherein the substrate is chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, ellipticlly polarizing substrates, and reflective substrates.
78. The optical element of claim 72 wherein the at least one photochromic compound has an average absorption ratio greater than 2.3 as determined according to CELL
METHOD.
79. The optical element of claim 72 wherein the at least partial coating further comprises at least one other organic photochromic compound having at least one activated absorption maxima within the range of 300 nm to 1000 nm, inclusive.
80. An optical element comprising:
a substrate; and a polymeric sheet connected to at least a portion of the substrate, the polymeric sheet comprising at least one thermally reversible photochromic compound adapted to have an first state, a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL
METHOD .
81. An optical element comprising:
a substrate; and a polymeric sheet connected to at least a portion of the substrate, said polymeric sheet comprising at least one photochromic compound, wherein the photochromic compound comprises:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c-[Q1 -[S2]d ]d'-[Q2 -[S3]e ]e'-[Q3 -[S4]f]f' -S5 -P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:

(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24.
alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
82. The optical element of claim 81 wherein the at least one photochromic compound has an average absorption ratio greater than 2.3 as determined according to CELL
METHOD.
83. A display element comprising:
a first substrate having a first surface;
a second substrate having a second surface, wherein the second surface of the second substrate is opposite and spaced apart from the first surface of the first substrate so as to define an open region; and a fluid material comprising at least one thermally reversible photochromic compound positioned within the open region defined by the first surface of the first substrate and the second surface of the second substrate, wherein the thermally reversible photochromic compound is adapted to have at least a first state and a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD
84. A display element comprising:
a first substrate having a first surface;
a second substrate having a second surface, wherein the second surface of the second substrate is opposite and spaced apart from the first surface of the first substrate so as to define an open region; and a fluid material comprising at least one photochromic compound positioned within the open region defined by the first surface of the first substrate and the second surface of the second substrate, wherein the photochromic compound comprises:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
- [S1]c -[Q1 -[S2]d]d' -[Q2 -[S3]e]e' -[Q3 -[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
85. The display element of claim 84 wherein the display element is chosen from screens, monitors, and security elements.
86. The display element of claim 85 wherein the security elements are variable, linearly polarizing, optical security elements.
87. The display element of claim 84 wherein the first substrate and the second substrate are independently chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, ellitpically polarizing substrates, and reflective substrates.
88. The display element of claim 84 wherein the at least one photochromic compound has an average absorption ratio greater than 2.3 as determined according to CELL
METHOD.
89. The display element of claim 84 wherein the fluid material further comprises at least one other organic photochromic compound having at least one activated absorption maxima within the range of 300 nm to 1000 nm, inclusive.
90. A security element comprising:
a substrate; and at least one thermally reversible photochromic compound connected to at least a portion of the substrate, the thermally reversible photochromic compound being adapted to have an first state, a second state, and an average absorption ratio greater than 2.3 in at least one state as determined according to CELL METHOD
91. A security element comprising:
a substrate; and at least one photochromic compound connected to at least a portion of the substrate, wherein the at least one photochromic compound comprises:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a non-thermally reversible fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by:
-[S1]c -[Q1 -[S2]d]d'-[Q2 -[S3]e]e'-[Q3 -[S4]f]f' -S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C1-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 1 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)g-, -(CH2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, C(O)-,C.ident.C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d' + e' + f' is at least 1.
92. The security element of claim 91 wherein the at least one photochromic compound has an average absorption ratio greater than 2.3 as determined according to CELL
METHOD.
93. The security element of claim 91 wherein the substrate is chosen from access cards and passes; negotiable instruments and non-negotiable instruments; government documents; consumer goods; credit cards; and merchandise tags, labels and packaging.
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