Xylose-derived thionocarbamates as a synthetic handle towards a functional platform of sugar-based polymers

James R. Runge, Bethan Davies, Antoine Buchard*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The derivatisation of d-xylose with potassium thiocyanate is presented as a versatile synthetic handle towards functional synthetic carbohydrate polymers. The reactivity of the resulting 1,3-oxazolidine-2-thione (OZT) group with alkyl bromides is ubiquitous and, herein, has been exploited to synthesise seven bio-derived monomers with different pendant functionalities. These monomers were polymerised with dithiols to yield functional poly(ester-thioethers) with a broad spectrum of properties. From a single non-functionalised OZT-polymer, a variety of post-polymerisation modification approaches are possible to functionalise the materials with different pendant groups. These results present a novel simple methodology to tailor the properties of synthetic carbohydrate polymers to different applications.

Original languageEnglish
Pages (from-to)3149-3156
Number of pages8
JournalPolymer Chemistry
Volume15
Issue number31
DOIs
Publication statusPublished - 15 Jul 2024

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