Advancing Recyclable Thermosets through C═C/C═N Dynamic Covalent Metathesis Chemistry

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Advancing Recyclable Thermosets through C═C/C═N Dynamic Covalent Metathesis Chemistry
Title:
Advancing Recyclable Thermosets through C═C/C═N Dynamic Covalent Metathesis Chemistry
Journal Title:
Journal of the American Chemical Society
Keywords:
Publication Date:
24 July 2024
Citation:
Zheng, J., Feng, H., Zhang, X., Zheng, J., Ng, J. K. W., Wang, S., Hadjichristidis, N., & Li, Z. (2024). Advancing Recyclable Thermosets through C═C/C═N Dynamic Covalent Metathesis Chemistry. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.4c05346
Abstract:
Thermoset polymers have become integral to our daily lives due to their exceptional durability, making them feasible for a myriad of applications; however, this ubiquity also raises serious environmental concerns. Covalent adaptable networks (CANs) with dynamic covalent linkages that impart efficient reprocessibility and recyclability to thermosets have garnered increasing attention. While various dynamic exchange reactions have been explored in CANs, many rely on the stimuli of active nucleophilic groups and/or catalysts, introducing performance instability and escalating the initial investment. Herein, we propose a new direct and catalyst-free C=C/C=N metathesis reaction between α-cyanocinnamate and aldimine as a novel dynamic covalent motif for constructing recyclable thermosets. This chemistry offers mild reaction conditions (room temperature and catalyst-free), ensuring high yields and simple isolation procedures. By incorporating dynamic C=C/C=N linkages into covalently crosslinked polymer networks, we obtained dynamic thermosets that exhibit both malleability and reconfigurability. The resulting tunable dynamic properties, coupled with the high thermal stability and recyclability of the C=C/C=N linkage-based networks, enrich the toolbox of dynamic covalent chemistry.
License type:
Publisher Copyright
Funding Info:
This research / project is supported by the Agency for Science, Technology and Research - RIE2025 Manufacturing, Trade and Connectivity (MTC) Programmatic Fund
Grant Reference no. : M22K9b0049

This research / project is supported by the Agency for Science, Technology and Research - Career Development Fund
Grant Reference no. : C210812008
Description:
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see 10.1021/jacs.4c05346.
ISSN:
0002-7863
1520-5126
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