Selective bromination of perylene diimides and derivatives thereof under mild conditions

Abstract

The present invention is directed to novel process for the preparation of regioselective perylenediimides derivatives, specifically mono and dibrominated derivatives.

What is claimed is: 
     
         1 . A perylene-diimide compound represented by the structure of formula 4: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are the same or different comprising substituted or unsubstituted linear or branched alkyl group, substituted or unsubstituted saturated carbocyclic or heterocyclic ring or aryl; 
         R 3  is saturated or unsaturated heterocyclic ring; saturated or unsaturated carbocyclic ring, alkyl, alkylene or Z-perylene; and 
         Z is 1,4 phenyl, aryl, cycloalkyl, heterocycle, olefin, azo, amide, C═N, N═C, carbonyl, 1,4 divinylbenzene, piperidine; and 
         optionally a metal or a metal ion is coordinated to said perylene diimide compound forming a metal complex with said compound. 
       
     
     
         2 . The compound of  claim 1 , wherein said metal or metal ion comprises Pd, Pt, Fe, Cu, Ag, Rh, Ir, Ru or Os. 
     
     
         3 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 5: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 6: 
       
         
           
           
               
               
           
         
       
     
     
         8 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 9: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 10: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 13: 
       
         
           
           
               
               
           
         
       
     
     
         11 . The compound of  claim 1 , wherein said compound is represented by the structure of compound 16: