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Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers.

Publication ,  Journal Article
Petersen, SR; Prydderch, H; Worch, JC; Stubbs, CJ; Wang, Z; Yu, J; Arno, MC; Dobrynin, AV; Becker, ML; Dove, AP
Published in: Angewandte Chemie (International ed. in English)
April 2022

The remarkable elasticity and tensile strength found in natural elastomers are challenging to mimic. Synthetic elastomers typically feature covalently cross-linked networks (rubbers), but this hinders their reprocessability. Physical cross-linking 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.

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Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

April 2022

Volume

61

Issue

17

Start / End Page

e202115904

Related Subject Headings

  • Organic Chemistry
  • Isosorbide
  • Hydrogen Bonding
  • Elastomers
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Petersen, S. R., Prydderch, H., Worch, J. C., Stubbs, C. J., Wang, Z., Yu, J., … Dove, A. P. (2022). Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers. Angewandte Chemie (International Ed. in English), 61(17), e202115904. https://doi.org/10.1002/anie.202115904
Petersen, Shannon R., Hannah Prydderch, Joshua C. Worch, Connor J. Stubbs, Zilu Wang, Jiayi Yu, Maria C. Arno, Andrey V. Dobrynin, Matthew L. Becker, and Andrew P. Dove. “Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers.Angewandte Chemie (International Ed. in English) 61, no. 17 (April 2022): e202115904. https://doi.org/10.1002/anie.202115904.
Petersen SR, Prydderch H, Worch JC, Stubbs CJ, Wang Z, Yu J, et al. Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers. Angewandte Chemie (International ed in English). 2022 Apr;61(17):e202115904.
Petersen, Shannon R., et al. “Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers.Angewandte Chemie (International Ed. in English), vol. 61, no. 17, Apr. 2022, p. e202115904. Epmc, doi:10.1002/anie.202115904.
Petersen SR, Prydderch H, Worch JC, Stubbs CJ, Wang Z, Yu J, Arno MC, Dobrynin AV, Becker ML, Dove AP. Ultra-Tough Elastomers from Stereochemistry-Directed Hydrogen Bonding in Isosorbide-Based Polymers. Angewandte Chemie (International ed in English). 2022 Apr;61(17):e202115904.
Journal cover image

Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

April 2022

Volume

61

Issue

17

Start / End Page

e202115904

Related Subject Headings

  • Organic Chemistry
  • Isosorbide
  • Hydrogen Bonding
  • Elastomers
  • 34 Chemical sciences
  • 03 Chemical Sciences