Thiol-substituted copolylactide: synthesis, characterization and post-polymerization modification using thiol–ene chemistry

Abstract

The synthesis of a copolylactide that is substituted with pendent thiol side chains is described. The copolymer is prepared by the ring-opening copolymerization of a new monomer, 3,6-bis(4-methoxybenzylthiomethyl)-1,4-dioxane-2,5-dione, with L-lactide to afford poly(lactide-co-(4-methoxybenzylthio)methylglycolide) (MBT-PL). Debenzylation of MBT-PL affords poly(lactide-co-mercaptomethylglycolide), thiol-PL. We demonstrate the modification of thiol-PL by addition to a variety of electron-deficient alkenes: N-phenylmaleimide, N-phenyl acrylate and acrylonitrile.