Chemically Triggered Click and Declick Reactions: Application in Synthesis and Degradation of Thermosetting Plastics,ACS Macro Letters

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Chemically Triggered Click and Declick Reactions: Application in Synthesis and Degradation of Thermosetting Plastics
ACS Macro Letters ( IF 5.1 ) Pub Date : 2021-08-31 , DOI: 10.1021/acsmacrolett.1c00548
Tianhong Wu ₁ , Tianyu Liang _{1,

2} , Wei Hu _{1,

2} , Meiqing Du ₁ , Sijia Zhang ₃ , Yanfeng Zhang ₃ , Eric V Anslyn ₄ , Xiaolong Sun ₁

Affiliation

In this Letter, we report that two amines can be coupled together rapidly and quantitatively through amine–thiol scrambling using a bisvinylogous thioester conjugate acceptor under mild conditions. The resulting bisvinylogous amide conjugate acceptors can be decoupled via an ethylene diamine-induced cyclization. Four representative conjugate acceptors have been utilized in the couple–decouple reactions, which were monitored and characterized by nuclear magnetic resonance, high-resolution mass spectrometry, and UV–vis spectroscopy. Further, we applied these small-molecule-based “click–declick” reactions to polymer synthesis and degradation. Highly cross-linked polymers, i.e., plastics, were quantitatively synthesized by simple reactions between commercial tris(2-aminoethyl)amine and the conjugate acceptors without solvent and any initiator or catalyst through ball milling within 60 min. Significantly, these thermosetting plastics can be degraded within 3–24 h via addition of ethylene diamine. The multiple architectures, application to plastics synthesis, and chemically triggered clean degradation to the thermosets at mild conditions with little input of energy herald a new generation of “intelligent” materials.

中文翻译：

化学触发点击和点击反应：在热固性塑料合成和降解中的应用

在这封信中，我们报道了两种胺可以通过胺-硫醇加扰在温和条件下使用双乙烯基硫酯共轭受体快速定量地偶联在一起。所得双乙烯基酰胺共轭受体可通过乙二胺诱导的环化作用解偶联。四种具有代表性的共轭受体已用于偶合-解偶反应，通过核磁共振、高分辨率质谱和紫外-可见光谱对其进行监测和表征。此外，我们将这些基于小分子的“click-declick”反应应用于聚合物合成和降解。高度交联的聚合物，即塑料，通过商业三（2-氨基乙基）胺与共轭受体之间的简单反应定量合成，无需溶剂和任何引发剂或催化剂，通过球磨在 60 分钟内完成。值得注意的是，这些热固性塑料可以通过添加乙二胺在 3-24 小时内降解。多种体系结构、塑料合成应用以及在温和条件下以化学方式引发热固性材料的清洁降解，几乎没有能量输入，预示着新一代“智能”材料的出现。

更新日期：2021-09-21

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