Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from D- and L-Xylose

Antoine Buchard, Thomas McGuire, Jessica Bowles, Edward Deane, Elliot Farrar, Matthew Grayson

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
4 Downloads (Pure)

Abstract

Manipulating the stereochemistry of polymers is a powerful method to alter their physical properties. Despite the chirality of monosaccharides, reports on the impact of stereochemistry in natural polysaccharides and synthetic carbohydrate polymers remain absent. Herein, we report the cocrystallization of regio‐ and stereoregular polyethers derived from D- and L-xylose, leading to enhanced thermal properties compared to the enantiopure polymers. To the best of our knowledge, this is the first example of a stereocomplex between carbohydrate polymers of opposite chirality. In contrast, atactic polymers obtained from a racemic mixture of monomers are amorphous. We also show that the polymers hydroxyl groups are amenable to post-polymerization functionalization. These strategies afford a family of carbohydrate polyethers, the physical and chemical properties of which can both be controlled, and which opens new possibilities for polysaccharide mimics in biomedical applications or as advanced materials.
Original languageEnglish
Pages (from-to)4524 –4528
Number of pages5
JournalAngewandte Chemie-International Edition
Volume60
Issue number0
Early online date22 Nov 2020
DOIs
Publication statusPublished - 23 Feb 2021

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