Thiol-Anhydride Dynamic Reversible Networks

Angewandte Chemie
Maciej PodgórskiChristopher N Bowman

Abstract

The reaction of thiols and anhydrides to form ring opened thioester/acids is shown to be highly reversible and it is accordingly employed in the fabrication of covalent adaptable networks (CANs) that possess tunable dynamic covalent chemistry. Maleic, succinic, and phthalic anhydride derivatives were used as bifunctional reactants in systems with varied stoichiometries, catalyst, and loadings. Dynamic characteristics such as temperature-dependent stress relaxation, direct reprocessing and recycling abilities of a range of thiol-anhydride elastomers, glasses, composites and photopolymers are discussed. Depending on the catalyst strength, 100 % of externally imposed stresses were relaxed in the order of minutes to 2 hours at mild temperatures (80-120 °C). Pristine properties of the original materials were recovered following up to five cycles of a hot-press reprocessing technique (1 h/100 °C).

References

Mar 2, 2002·Science·Xiangxu ChenFred Wudl
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Mar 23, 2010·Macromolecules·Christopher J KloxinChristopher N Bowman
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Jan 10, 2019·Angewandte Chemie·Progyateg Chakma, Dominik Konkolewicz

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Citations

Oct 29, 2020·Chemical Society Reviews·Filip Van LijsebettenFilip E Du Prez
Dec 29, 2020·ACS Applied Materials & Interfaces·Maciej PodgórskiChristopher N Bowman
May 8, 2021·Macromolecular Rapid Communications·Progyateg ChakmaDominik Konkolewicz
Jun 15, 2021·Journal of the American Chemical Society·Christian TaplanFilip E Du Prez
May 13, 2021·Angewandte Chemie·Dong ZhaoXuzhou Yan
Dec 12, 2020·ACS Applied Materials & Interfaces·Xiaming Feng, Guoqiang Li
Aug 27, 2021·ACS Applied Materials & Interfaces·Mohand O SaedEugene M Terentjev
Sep 16, 2021·Journal of the American Chemical Society·Filip Van LijsebettenFilip E Du Prez

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