Vapor deposited electro-optic films self-assembled through hydrogen bonding

Abstract

The present invention introduces a novel route toward microstructural orientation into organic films, using multiple hydrogen-bonding to self-assemble chromophore molecules into electro-optic films in a net polar orientation. High-quality, thick films (up to micrometers) with molecular net dipole orientations can be fabricated under vacuum in hours. The film microstructure is intrinsically acentric; and the orientation is robust.

1 . A method of using hydrogen-bonding for acentric chromophore orientation, said method comprising:
 providing a substrate comprising one of a hydrogen bond-forming hydrogen donor moiety and a hydrogen bond-forming hydrogen acceptor moiety;   contacting said substrate with a vapor phase chromophore compound having a first terminal moiety comprising a plurality of hydrogen bond-forming hydrogen donor groups, and a second terminal moiety comprising a plurality of hydrogen bond-forming hydrogen acceptor groups; and   contacting said first chromophore compound with a second said vapor phase chromophore compound, wherein said first and second chromophore compounds are of a formula
   D-Ar 1   x X═X n Ar 2   y -A 
   
       wherein D is a moiety comprising a plurality of hydrogen bond-forming hydrogen donor groups; A is a moiety comprising a plurality of hydrogen bond-forming hydrogen acceptor groups; (—X═X—) is a π-bonded component comprising at least one of carbon and a heteroatom; n, x and y are independently ≧0; and x+y is ≧1. 
     
     
         2 . The method of  claim 1  wherein said first terminal moiety is selected from 
       
         
           
           
               
               
           
         
       
       wherein R 1 -R 3  are independently selected from hydrogen, electron-donating substituents and electron-withdrawing substituents. 
     
     
         3 . The method of  claim 1  wherein said second terminal moiety is selected from 
       
         
           
           
               
               
           
         
       
       wherein R 7  is selected from hydrogen, electron-donating substituents and electron-withdrawing substituents. 
     
     
         4 . The method of  claim 1  comprising providing a substrate comprising hydroxy moieties, reacting said moieties with an aminoalkyltrialkoxysilane, and reacting said hydroxy-silane reaction product with a melamine moiety, for hydrogen-bonding with said chromophore.