Synthesis of poly(vinyl acetate) with fluorescence via a combination of RAFT/MADIX and click chemistry

A novel w-azido-functionalized RAFT reagent, O-(2-azido-ethyl) S-benzyl dithiocarbonate (AEBDC) was synthesized and subsequently employed to mediate the reversible addition-fragmentation chain transfer (RAFT) polymerization of vinyl acetate (VAc) to prepare end-functionalized polymers. The polymerization results showed that the RAFT polymerizations of VAc could be well controlled using AEBDC as the RAFT agent. Number-average molecular weights (M(nGPC)) increased linearly with monomer conversion, and molecular weight distributions were relatively narrow. (1)H NMR spectrum of the poly(vinyl acetate) (PVAc) confirmed the existence of functional azido group at the end of the polymers chains. The omega-azido-terminated polymers were coupled by click chemistry with a fluorescent alkyne, 7-propinyloxy coumarin, to prepare fluorescent PVAc. The fluorescence properties of the PVAc homopolymers before and after coupling with 7-propinyloxy coumarin in CH(2)Cl(2) solution were investigated. (C) 2008 Elsevier Ltd. All rights reserved.