Adjustable chromophore compounds and materials incorporating such compounds

Abstract

The present invention is directed to adjustable chromophore compounds and materials (e.g., ophthalmic lens materials) incorporating those compounds. The adjustable chromophore compounds include a chemical moiety that structurally changes upon exposure to predetermined electromagnetic radiation (e.g., two photon radiation) as well as lens materials, particularly intraocular lens materials that incorporate those compounds.

1 . An adjustable chromophore comprising:
 a compound of the formula:
     B—X;    
   wherein:   v) B is a base chromophore compound; and   vi) X is an adjustable chemical moiety that forms a remaining chemical moiety (C) upon exposure to predetermined electromagnetic radiation thereby forming the compound:
     B—C;    
   vii) the compound B—C provided greater light absorption than the compound B—X; and   viii) the remaining chemical moiety (C) includes a conjugated double bond.   
     
     
         2 . A chromophore as in  claim 1  wherein the base chromophore compound is selected from the group consisting of benzotriazoles, benzophenones, azo dyes and cinnamate esters. 
     
     
         3 . A chromophore as in  claim 2  wherein the base chromophore compound is a benzotriazole. 
     
     
         4 . A chromophore as in  claim 1  wherein the compound B—C absorbs a significant amount of UV light, blue light or both. 
     
     
         5 . A chromophore as in  claim 3  wherein the compound B—C absorbs a significant amount of blue light. 
     
     
         6 . A chromophore as in  claim 1  wherein the adjustable chemical moiety X is a cyclic moiety. 
     
     
         7 . A chromophore as in  claim 1  wherein the adjustable chemical moiety X is dicyclopentadiene. 
     
     
         8 . A lens comprising:
 a polymeric material; and   the adjustable chromophore compound of  claim 1  distributed within the polymeric material;   wherein the material can absorb light at progressively greater wavelengths as greater amounts of the compound B—C are formed from the adjustable compound B—X.   
     
     
         9 . A method of adjusting a lens in vivo or in vitro comprising:
 directing the predetermined electromagnetic radiation at the polymeric material of  claim 8  to form the compound B—C either prior to or after implantation of the lens in the eye.   
     
     
         10 . An adjustable chromophore system, comprising:
 a compound of the formula:
     B—X or B—C    
   as part of the reactive system:
     B—X⇄B—C    
   wherein:   i) B is a base chromophore compound;   ii) X is an adjustable chemical moiety that forms remaining chemical moiety (C) upon exposure to first predetermined electromagnetic radiation thereby forming the compound B—C;   iii) the compound B—C provides greater light absorption than the compound B—X;   iv) the remaining chemical moiety (C) includes a conjugated double bond; and   v) optionally, the compound B—C forms the compound B—X upon exposure to second predetermined electromagnetic radiation either with or without the aid of a separable group (S).   
     
     
         11 . A system as in  claim 10  wherein the base chromophore compound is selected from the group consisting of benzotriazoles, benzophenones, azo dyes and cinnamate esters. 
     
     
         12 . A system as in  claim 11  wherein the base chromophore compound is a benzotriazole. 
     
     
         13 . A system as in  claim 10  wherein the compound B—C absorbs a significant amount of UV light, blue light or both. 
     
     
         14 . A system as in  claim 10  wherein the compound B—C absorbs a significant amount of blue light. 
     
     
         15 . A system as in  claim 10  wherein the adjustable chemical moiety X is a cyclic moiety. 
     
     
         16 . A system as in  claim 10  wherein the adjustable chemical moiety X is dicyclopentadiene. 
     
     
         17 . A lens comprising:
 a polymeric material; and   the adjustable chromophore system of  claim 10  distributed within the polymeric material.   
     
     
         18 . A method of adjusting a lens in vivo or in vitro comprising:
 directing the predetermined first or second electromagnetic radiation at the lens of  claim 17  to form the compound B—C or B—X either prior to or after implantation of the lens in the eye.   
     
     
         19 . An adjustable chromophore system, comprising:
 a compound of the formula:
     B—X or B—C    
   as part of the reactive system:
     B—X⇄B—C    
   wherein:   i) B is a base chromophore compound;   ii) X is an adjustable chemical moiety that forms remaining chemical moiety (C) upon exposure to first predetermined electromagnetic radiation thereby forming the compound B—C;   iii) the compound B—C provides greater light absorption than the compound B—X;   iv) the remaining chemical moiety (C) includes a conjugated double bond;   v) the compound B—C forms the compound B—X upon exposure to second predetermined electromagnetic radiation either with or without the aid of a separable group (S);   vi) the base chromophore compound is selected from the group consisting of benzotriazoles, benzophenones, azo dyes and cinnamate esters;   vii) the compound B—C absorbs a significant amount of UV light, blue light or both; and   viii) the adjustable chemical moiety X is a cyclic moiety.   
     
     
         20 . A lens comprising:
 a polymeric material; and   the adjustable chromophore system of  claim 19  distributed within the polymeric material.   
     
     
         21 . A method of adjusting a lens in vivo or in vitro comprising:
 directing the predetermined first or second electromagnetic radiation at the lens of  claim 20  to form the compound B—C or B—X either prior to or after implantation of the lens in the eye.