Novel substituted-polyaryl chromophoric compounds

Abstract

The invention provides for novel substituted-polyaryl chromophoric compounds which desirably comprise a single diazo group, and optimally include a plurality of diazo groups. Preferably the chromophores exhibit optical nonlinear second-order properties and have unique absorption maximum and other chromophoric properties that make them useful for, among other things, multifunctional optical switches or waveguides.

1 .- 8 . (canceled)  
   
   
       9 . A compound of the formula:  
     
       
         
         
             
             
         
       
       wherein Ar 1  is selected from the group consisting of:  
       
         
           
           
               
               
           
         
         Ar 2  is selected from the group consisting of:  
         
           
             
             
                 
                 
             
           
         
       
       and if m=1; R 1  is an electron donating group selected from the group consisting of hydrogen, hydroxy, amino, and C 1-12 alkoxy (optionally substituted with hydroxyl or amino), C 1-12 dialkylamino (substituted with hydroxyl or amino), C 1-12 alkylarylamino (optionally substituted with hydroxyl or amino), and diarylamino (optionally substituted with hydroxyl or amino); R 2  is hydrogen, C 1-12 alkyl, carboxy, hydroxy, C 1-12 alkoxy, or halo; and at least one of the groups R 3 , R 4  and R 5  is an electron withdrawing group selected from the group consisting of hydrogen, cyano, COR 2 , C 1-12 mono- or polyhaloalkyl, C 1-12 alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C 1-12 alkylsulfonyl (optionally substituted) and arylsulfonyl (optionally substituted); while the other of the groups R 3 , R 4  and R 5  are, independently, C 1-12 alkyl, hydroxy, C 1-12 alkoxy, amino, C 1-12 alkylarylamino (optionally substituted with hydroxyl or amino), diarylamino (optionally substituted with hydroxyl or amino), hydrogen, cyano, COR2, C 1-12 mono- or polyhaloalkyl, C 1-12 alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C 1-12 alkylsulfonyl (optionally substituted), or arylsulfonyl (optionally substituted); and  
       if m=2-9; R 1  is an electron donating group selected from the group consisting of hydrogen, hydroxy, amino, C 1-12 alkoxy (optionally substituted with hydroxyl or amino), C 1-12 dialkylamino (optionally substituted with hydroxyl or amino), C 1-12 alkylarylamino (optionally substituted with hydroxyl or amino), and diarylamino (optionally substituted with hydroxyl or amino); R 2  is hydrogen, C 1-12 alkyl, carboxy, hydroxy, C 1-12 alkoxy, or halo; and at least one of the groups R 3 , R 4  and R 5  is an electron withdrawing group selected from the group consisting of hydrogen, cyano, COR 2 , C 1-12 mono- or polyhaloalkyl, C 1-12 alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C 1-12 alkylsulfonyl (optionally substituted), and arylsulfonyl (optionally substituted); while the other of the groups R 3 , R 4  and R 5  are, independently, C 1-12 alkyl, hydroxy, C 1-12 alkoxy, amino, C 1-12 alkylarylamino (optionally substituted with hydroxyl or amino), diarylamino (optionally substituted with hydroxyl or amino), hydrogen, cyano, COR 2 , C 1-12 mono- or polyhaloalkyl, C 1-12 alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C 1-12 alkylsulfonyl (optionally substituted), or arylsulfonyl (optionally substituted).  
     
   
   
       10 . The compound in accordance with  claim 9  wherein R 2  is hydrogen, methyl, or methoxy; R 3 , R 4  and R 5  are, independently, hydrogen, methylsulfonyl, or nitro; and m=2-9.  
   
   
       11 . The compound in accordance with  claim 10  wherein R 3 , R 4  and R 5  are, independently, hydrogen or nitro; and m=2-9.  
   
   
       12 . The compound in accordance with  claim 9  wherein R 3 , R 4  and R 5  are, independently, hydrogen or methylsulfonyl; and m=2-9.  
   
   
       13 . A composition comprising an effective amount of the compound in accordance with  claim 9  in admixture with a optically acceptable polymer.  
   
   
       14 . A composition comprising an effective amount of the compound in accordance with  claim 9  attached to a optically acceptable polymer with a C0-30 spacer.  
   
   
       15 . A use of a compound in accordance with  claim 9  in an optical waveguide or an optical switch.  
   
   
       16 . A use of a compound in accordance with  claim 9  in an optical waveguide or an optical switch.