Ultra-tough elastomers from stereochemistry-directed hydrogen bonding in isosorbide-based polymers

Shannon Petersen, Hannah Prydderch, Josh Worch, Connor Stubbs, Zilu Wang, Jiayi Yu, Maria Chiara Arno, Andrey Dobrynin, Matthew L Becker, Andrew Dove

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The remarkable elasticity and tensile strength found in natural elastomers are challenging to mimic. Synthetic elastomers typically feature covalently crosslinked networks (rubbers), but this hinders their reprocessability. Physical crosslinking via hydrogen bonding or ordered crystallite domains can afford reprocessable elastomers, but often at the cost of performance. Herein, we report the synthesis of ultra-tough, reprocessable elastomers based on linear alternating polymers. The incorporation of a rigid isohexide adjacent to urethane moieties affords elastomers with exceptional strain hardening, strain rate dependent behavior, and high optical clarity. Distinct differences were observed between isomannide and isosorbide-based elastomers where the latter displays superior tensile strength and strain recovery. These phenomena are attributed to the regiochemical irregularities in the polymers arising from their distinct stereochemistry and respective inter-chain hydrogen bonding.
Original languageEnglish
Article numbere202115904
JournalAngewandte Chemie (International Edition)
Issue number17
Early online date15 Feb 2022
Publication statusE-pub ahead of print - 15 Feb 2022

Bibliographical note

Funding Information:
The authors gratefully acknowledge financial support from Duke University and the National Science Foundation under the grant DMR1535412 (A.V.D.) and DMR‐1507420 (M.L.B.). J.C.W. acknowledges funding from the European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska‐Curie grant agreement Nos 751150. A.P.D., M.C.A. and C.J.S. thank the European Research Council (Grant Number 681559) for funding. H.P. acknowledges funding from the Leverhulme Trust (RPG‐2015‐120).

Publisher Copyright:
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH


  • Elastomers
  • Isomannide
  • Isosorbide
  • Polyurethane
  • Stereochemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)


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