Issue 29, 2021

Polymers from sugars and CS2: ring opening copolymerisation of a d-xylose anhydrosugar oxetane

Abstract

A D-xylose anhydro sugar derivative (1) has been applied in the ring-opening copolymerisation (ROCOP) with CS2 to form a polythiocarbonate (poly(CS2-co-1)) with high head-head/tail-tail regioselectivity towards alternating thiono- and trithiocarbonate linkages (up to 95%). Through variation of the reaction parameters (e.g. temperature and CS2 stoichiometry), some control over the regioselectivity (head-head/tail-tail linkages 57–95%) and the nature of the polymer linkages is possible. Conditions can also be tailored to enable the facile isolation of a polymerisable cyclic xanthate, 2. Kinetic experiments suggest that across the range of temperatures studied, the formation of poly(CS2-co-1) proceeds at least partially by direct copolymerisation of 1 and CS2, without necessarily going through the ring-opening polymerisation (ROP) of 2. Poly(CS2-co-1) exhibits partial chemical recyclability into cyclic monomer 2 (up to 45% after 20 h at 110 °C with [poly(CS2-co-1)]0 = 1.34 mol L−L). Finally, rapid degradation (<1 h) of poly(CS2-co-1) is possible under UV radiation (λ = 365 nm) and is accelerated in the presence of tris(trimethylsilyl)silane (TTMSS).

Graphical abstract: Polymers from sugars and CS2: ring opening copolymerisation of a d-xylose anhydrosugar oxetane

Supplementary files

Article information

Article type
Paper
Submitted
04 Jun 2021
Accepted
06 Jul 2021
First published
06 Jul 2021
This article is Open Access
Creative Commons BY license

Polym. Chem., 2021,12, 4253-4261

Polymers from sugars and CS2: ring opening copolymerisation of a D-xylose anhydrosugar oxetane

T. M. McGuire and A. Buchard, Polym. Chem., 2021, 12, 4253 DOI: 10.1039/D1PY00753J

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