Suzuki coupling of aryl organics on diamond

Abstract

We demonstrate a facile method for the Suzuki coupling of aryl molecules on the diamond surface. This is a more versatile alternative compared to previous coupling methods based on alkene linkers because it opens up possibilities for the application of diamond in molecular electronics and photovoltaics. The diamond surface is premodified with aryldiazonium salt in order to functionalize it with aryl halide or aryl boronic acid, and these are then used as synthons in the subsequent Suzuki coupling to aryl molecules. This method is highly specific and can be used for the uninterrupted molecular conjugation of diamond to a large class of organic molecules. As a proof of concept, we also demonstrate a diamond-fullerene photocurrent converter by using Suzuki coupled oligothiophene as the conjugated linker between diamond (electron donor) and fullerene (electron acceptor). © 2008 American Chemical Society.