Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers,Macromolecules

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Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers
Macromolecules ( IF 5.1 ) Pub Date : 2020-03-17 , DOI: 10.1021/acs.macromol.9b02747
Xu Chen ₁ , Tianwen Bai ₂ , Rong Hu ₁ , Bo Song ₁ , Lin Lu ₁ , Jun Ling ₂ , Anjun Qin ₁ , Ben Zhong Tang _{1,

3}

Affiliation

Synthesis of nitrogen-containing polymers has always been a hot research topic for their broad applications as functional materials. In this work, we established new, spontaneous, and atom-economic amino-yne click polymerization for the construction of regio-/stereoregular nitrogen-containing polymers. Aroylacetylenes, which could be facilely prepared without using water-sensitive ethynylmagnesium bromide and harsh reaction conditions, could be polymerized with amines in the absence of any catalyst under ambient conditions, and poly(β-enaminone)s with high weight-average molecular weights (M_w of up to 49 400) could be produced in excellent yields (up to 99%). Moreover, sole E-isomer-containing polymers could be obtained efficiently from the click polymerization of aroylacetylenes and secondary amines, whereas absolute Z-configuration products were prepared when using primary amines. In addition, poly(β-enaminone)s could be degraded upon the addition of Lewis acid and primary amines in aqueous solution and definite compounds could be generated, proving their wide application prospects as degradable nitrogen-containing polymers.

中文翻译：

芳基乙炔基氨基-Click点击聚合成含氮聚合物

含氮聚合物的合成一直作为功能材料的广泛应用一直是研究的热点。在这项工作中，我们建立了新的，自发的，原子经济的氨基炔单击聚合技术，用于构建区域/立体不规则的含氮聚合物。可以不使用对水敏感的乙炔基溴化镁和苛刻的反应条件而容易地制备的芳酰基乙炔，可以在环境条件下在不存在任何催化剂的情况下与胺聚合，并且可以使用重均分子量高的聚（β-烯胺酮）（可以以极高的产率（高达99％）生产高达₄₉₄₀₀的Mw。此外，鞋底E可以通过芳酰基乙炔和仲胺的点击聚合有效地获得含β-异构体的聚合物，而当使用伯胺时，制备了绝对的Z-构型产物。此外，在水溶液中加入路易斯酸和伯胺后，聚（β-烯胺酮）可能会降解，并且可以生成确定的化合物，证明了其作为可降解含氮聚合物的广阔应用前景。

更新日期：2020-04-24

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