Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

Joshua C. Worch, Andrew C. Weems, Jiayi Yu, Maria C. Arno, Thomas R. Wilks, Robert T. R. Huckstepp, Rachel K. O'Reilly, Matthew L. Becker, Andrew P. Dove

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)
237 Downloads (Pure)


Biocompatible polymers are widely used in tissue engineering and biomedical device applications. However, few biomaterials are suitable for use as long-term implants and these examples usually possess limited property scope, can be difficult to process, and are non-responsive to external stimuli. Here, we report a class of easily processable polyamides with stereocontrolled mechanical properties and high-fidelity shape memory behaviour. We synthesise these materials using the efficient nucleophilic thiol-yne reaction between a dipropiolamide and dithiol to yield an α,β - unsaturated carbonyl moiety along the polymer backbone. By rationally exploiting reaction conditions, the alkene stereochemistry is modulated between 35-82% cis content and the stereochemistry dictates the bulk material properties such as tensile strength, modulus, and glass transition. Further access to materials possessing a broader range of thermal and mechanical properties is accomplished by polymerising a variety of commercially available dithiols with the dipropiolamide monomer.

Original languageEnglish
Article number3250
Number of pages11
JournalNature Communications
Issue number1
Early online date26 Jun 2020
Publication statusPublished - Dec 2020

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Physics and Astronomy(all)


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