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

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 efficien...

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Veröffentlicht in:Journal of the American Chemical Society 2024-08, Vol.146 (31), p.21612-21622
Hauptverfasser: Zheng, Jie, Feng, Hongzhi, Zhang, Xinglong, Zheng, Jianwei, Ng, Jeffrey Kang Wai, Wang, Sheng, Hadjichristidis, Nikos, Li, Zibiao
Format: Artikel
Sprache:eng
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Zusammenfassung: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 reprocessability 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 cross-linked 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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.4c05346