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

James R. Runge; Bethan Davies; Antoine Buchard

doi:10.1039/d4py00540f

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

James R. Runge, Bethan Davies, Antoine Buchard

York University

Research output: Contribution to journal › Article › peer-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 language	English
Journal	Polymer Chemistry
Early online date	15 Jul 2024
DOIs	https://doi.org/10.1039/d4py00540f
Publication status	E-pub ahead of print - 15 Jul 2024

Data Availability Statement

The data supporting this article have been included as part of the ESI

Funding

Analytical facilities were provided through the Material and Chemical Characterisation Facility (MC) at the University of Bath. Research funding from the UK Engineering and Physical Sciences Research Council (DTP studentship to JRR), and the Royal Society (UF160021 and URF\\R\\221027: fellowship to A B) is also acknowledged.

Funders	Funder number
Engineering and Physical Sciences Research Council
Royal Society	UF160021, URF\R\221027

ASJC Scopus subject areas

Bioengineering
Biochemistry
Polymers and Plastics
Organic Chemistry

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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.",

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N2 - 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.

AB - 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.

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JO - Polymer Chemistry

JF - Polymer Chemistry

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

Abstract

Data Availability Statement

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ASJC Scopus subject areas

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