Synthesis of amino acid-functionalized polymers (biohybrids) by anionic polymerization and hydrosilation chemistry

POLY 551

Roderic Quirk, quirk@polymer.uakron.edu and Sumana Roy Chowdhury, rc_sumana@hotmail.com. Maurice Morton Institute of Polymer Science, University of Akron, Akron, OH 44325
A versatile method for the anionic synthesis of well-defined polymer biohybrids has been developed. In the first step, a copolymer of styrene and (4-vinylphenyl)dimethylsilane (Mn=8600 g/mol) was prepared using alkyllithium-initiated anionic polymerization in benzene at room temperature. Subsequent hydrosilation reactions were carried out using the silyl-hydride groups on the polymer chain and allyl amine in the presence of Karstedt's catalyst. The final step was a condensation reaction between the amine functionality on the copolymer chain and the free carboxyl group in (N-carbobenzyloxy)-L-phenylalanine. This method provides a simple method to synthesize well-defined polymer biohybrids, utilizing anionic polymerization, followed by two, simple high yield steps, i.e. hydrosilation and condensation reactions. The polymeric products were characterized using SEC,carbon and proton NMR,FTIR and TLC analyses.