Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction,ACS Macro Letters

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Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction
ACS Macro Letters ( IF 5.1 ) Pub Date : 2021-09-16 , DOI: 10.1021/acsmacrolett.1c00550
Xinru Guo ₁ , Fei Gao ₁ , Fengbiao Chen ₁ , Jiang Zhong ₁ , Liang Shen ₁ , Cong Lin ₁ , Yangju Lin ₂

Affiliation

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.

中文翻译：

基于氨基炔点击反应的动态烯胺一键 Vitrimer

在这里，我们报告了通过氨基-炔点击化学制备基于动态烯胺-单键的玻璃体。与胺-乙酰乙酸缩合相反，氨基-炔点击反应产生由顺式/反式组成的动态烯胺-单基序(3:1) 异构体并具有相对较低的活化能（35 ± 3 kJ/mol 对 59 ± 6 kJ/mol），因为没有甲基取代基。与源自胺-乙酰乙酸缩合的参考 vitrimer 相比，所得的 vitrimer 网络具有优异的机械性能和更快的动态交换，它们分别归因于较少的网络缺陷和较少的空间位阻交换反应。最后，证明了高效的氨基-炔点击反应与仲胺底物相容，仲胺底物对胺-乙酰乙酸缩合反应的反应性较低。高效且无副产物的氨基炔反应为玻璃体制造提供了强大的化学工具，并且可能是密封和粘合应用的理想选择。

更新日期：2021-10-19

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