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Issue 8, 2018
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Thiol-substituted copolylactide: synthesis, characterization and post-polymerization modification using thiol–ene chemistry

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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.

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

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Publication details

The article was received on 17 Nov 2017, accepted on 30 Jan 2018 and first published on 07 Feb 2018


Article type: Paper
DOI: 10.1039/C7PY01930K
Citation: Polym. Chem., 2018,9, 1022-1031
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    Thiol-substituted copolylactide: synthesis, characterization and post-polymerization modification using thiol–ene chemistry

    P. P. Kalelkar and D. M. Collard, Polym. Chem., 2018, 9, 1022
    DOI: 10.1039/C7PY01930K

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