Boron containing perylene monoimides, a process for their production, their use as building blocks for the production of perylene monoimide derivatives, monoimide derivatives and their use in dye-sensitized solar cells

Abstract

Boron-comprising perylene monoimides and a process for producing the boron-comprising perylene monoimides are provided. The boron-comprising perylene monoimides are useful as building blocks for producing perylene monoimide derivatives and monoimide derivatives. The boron-comprising perylene monoimides are also useful for preparing dye-sensitized solar cells.

1 - 12 . (canceled) 
     
     
         13 . A process for the preparation of compounds of general formula IV 
       
         
           
           
               
               
           
         
         wherein the variables have the following meaning 
         R 13 , R 14  independently of each other aryl or hetaryl, 
         m 0 or 1, where in the case of in equal 1 R 14  is bound either to the 8 or 9 position of the perylene skeleton, 
         R 3  identical or different radicals hydrogen, alkyl, cycloalkyl, aryl, hetaryl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, diarylamino or dialkylamino, 
         n 0, 1, 2, 3 or 4 
         Y oxygen or NR 12 ,
 and 
 
         R 2  hydrogen, alkyl, cycloalkyl, aryl or hetaryl,
 or 
 a moiety of formula —Z-A, wherein 
 A is —COOM, —SO 3 M or —PO 3 M, 
 M hydrogen, alkali metal cation or [NR′] 4+ , 
 R′ hydrogen or alkyl, where the radicals R′ may be identical or different, 
 
         Z C 1 -C 6 -alkylene or 1,4-phenylene, where the phenylene radical may be substituted by one or more substituents alkyl, nitro, cyano and/or halogen, 
         comprising 
         reacting a compound of general formula I 
       
       
         
           
           
               
               
           
         
         
           wherein the variables have the following meaning 
         
         E 1 , E 2  a moiety of formula Ia 
       
       
         
           
           
               
               
           
         
         m 0 or 1, where in the case of m equal 1 E 2  is bound either to the 8 or 9 position of the perylene skeleton and is identical to E 1 , 
         W a bridging C 2  or C 3  moiety which may be substituted by one or more alkyl, 
         and the remaining variables R 3 , n and Y have the meaning as defined above with compounds of general formula Lg-R 13  and Lg-R 14  in the presence of a palladium containing catalyst under the conditions of the Suzuki coupling reaction. 
       
     
     
         14 . A process according to  claim 13  wherein in general formula IV the variables have the following meaning
 R 13 , R 14  independently of each other moieties of formulae IVa or IVb 
 
       
         
           
           
               
               
           
         
         R 15  hydrogen, alkyl, aryl, alkoxy, alkylthio or —NR 16 R 17 , where in case of two or more substituents (q equal or greater than 2) these may be identical or different, 
         q 0, 1, 2, 3, 4 or 5, 
         X C(R 18 R 19 ) 2 , NR 20 , oxygen or sulfur, 
         R 16  to R 20  hydrogen, alkyl, aryl or hetaryl. 
       
     
     
         15 . A process according to  claim 13  wherein in general formula IV
 Lg chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate or triflate. 
 
     
     
         16 . Compounds of general formula IV according to  claim 13 . 
     
     
         17 . A method of preparing a dye-sensitized solar cell comprising dying an electrode with compounds of general formula IV prepared according to  claim 13 . 
     
     
         18 . A dye-sensitized solar cell comprising compounds of general formula IV prepared according to  claim 13 .