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Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction
journal contribution
posted on 2021-09-16, 11:36 authored by Xinru Guo, Fei Gao, Fengbiao Chen, Jiang Zhong, Liang Shen, Cong Lin, Yangju LinHere,
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.
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yne reaction offersyne click reactionyne click chemistrysuperior mechanical propertiespowerful chemical toolmol ), owinglow reactivity towardfewer network defectsresulting vitrimer networkreference vitrimer derivedfaster dynamic exchangedynamic enaminevitrimer fabricationtrans side productpotentially desirableone motifmethyl substituentcis adhesion applicationsacetoacetate condensation