Well-controlled polymerization of 2-azidoethyl methacrylate at near room temperature and click functionalization

A functional monomer with a pendant azide moiety, 2-azidoethyl methacrylate (AzMA), was polymerized via reversible addition-fragmentation chain transfer (RAFT) polymerization with excellent control over the molecular weight distribution (PDI = 1.05-1.15). The subsequent copper-catalyzed Huisgen 1,3-dipolar cycloadditions of phenyl acetylene with polyAzMA was achieved at room temperature with high conversion. The resulting functional polymer exhibited identical H-1 NMR and IR spectra with the polymer of the same molecular structure but prepared by a pre-functionalization approach, confirming the retention of the azide side chains during the RAFT polymerization of AzMA. (c) 2007 Wiley Periodicals, Inc.