Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction.

Here, we report the fabrication of a dynamic enamine-one bond based vitrimer through amino-yne click chemistry. In contrast to amine-acetoacetate condensation, the amino-yne click reaction yields a dynamic enamine-one motif that is composed of cis/trans (3:1) isomers and has a relatively lower activation energy (35 ± 3 kJ/mol vs 59 ± 6 kJ/mol), owing to the absence of a methyl substituent. The resulting vitrimer network has superior mechanical properties and faster dynamic exchange than that of a reference vitrimer derived from amine-acetoacetate condensation, and they are attributed to the fewer network defects and the less sterically hindered exchange reaction, respectively. Lastly, the efficient amino-yne click reaction is demonstrated to be compatible with the secondary-amine substrate, which has a low reactivity toward the amine-acetoacetate condensation. The efficient and side product-free amino-yne reaction offers a powerful chemical tool for vitrimer fabrication and is potentially desirable for sealing and adhesion applications.

Citation

Xinru Guo, Fei Gao, Fengbiao Chen, Jiang Zhong, Liang Shen, Cong Lin, Yangju Lin. Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction. ACS macro letters. 2021 Oct 19;10(10):1186-1190

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PMID: 35549045

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