Catalyst‐Free Multicomponent Cyclopolymerizations of Diisocyanides, Activated Alkynes, and 1,4‐Dibromo‐2,3‐Butanedione: a Facile Strategy toward Functional Polyiminofurans Containing Bromomethyl Groups,Macromolecular Rapid Communications

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Catalyst‐Free Multicomponent Cyclopolymerizations of Diisocyanides, Activated Alkynes, and 1,4‐Dibromo‐2,3‐Butanedione: a Facile Strategy toward Functional Polyiminofurans Containing Bromomethyl Groups
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2020-09-28 , DOI: 10.1002/marc.202000463
Guinan Zhu ₁ , Weiqiang Fu ₁ , Binru Han ₁ , Jianbing Shi ₁ , Bin Tong ₁ , Zhengxu Cai ₁ , Junge Zhi ₂ , Yuping Dong ₁

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Polymers containing iminofuran (PIFs) are rarely reported due to the lack of simple and effective synthesis methods. In this work, a novel multicomponent cyclopolymerization (MCCP) of diisocyanides, activated alkynes, and 1,4‐dibromo‐2,3‐butanedione using catalyst‐free one‐pot reactions under mild conditions to prepare PIFs containing bromomethyl groups is reported. PIFs with good solubility and thermal stability are obtained with high M_ws (up to 19 600) and good yields (up to 89.5%) under optimized polymerization conditions. The structure of the PIFs is characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, and gel permeation chromatography. The photophysical properties indicate that polymers P1a2b3 and P1c2b3 have cluster‐triggered emission characteristics. Thin films made from PIFs quickly degrade under UV irradiation. Moreover, the obtained polymers are decorated with bromomethyl and carboxylate groups in the side chain, which can be postfunctionalized to prepare multifunctional materials, such as star branched polymers and biomedical carrier materials. Thus, this work not only enriches the field of polymerization based on isocyanates and activated alkynes but also provides a facile strategy toward functional iminofuran polymers.

中文翻译：

二异氰酸酯，活化的炔烃和1,4-二溴-2,3-丁二酮的无催化剂多组分环聚合：制备含有溴甲基基团的功能性聚亚氨基呋喃的简便策略

由于缺乏简单有效的合成方法，很少报道含亚氨基呋喃（PIF）的聚合物。在这项工作中，报道了在温和条件下使用无催化剂一锅法反应制备含溴甲基的PIF的新型二异氰酸酯，活化炔烃和1,4-二溴-2,3-丁二酮的多组分环聚合（MCCP）。在优化的聚合条件下，具有较高的M _w s（最高19 600）和良好的收率（最高89.5％），可获得具有良好溶解性和热稳定性的PIF 。PIF的结构以核磁共振，傅立叶变换红外光谱和凝胶渗透色谱为特征。光物理性质表明聚合物P1a2b3和P1c2b3具有簇触发的发射特性。由PIF制成的薄膜在紫外线照射下会迅速降解。此外，所获得的聚合物在侧链上装饰有溴甲基和羧酸酯基团，可以对其进行后官能化以制备多功能材料，例如星形支化聚合物和生物医学载体材料。因此，这项工作不仅丰富了基于异氰酸酯和活化炔烃的聚合领域，而且为功能性亚氨基呋喃聚合物提供了一种简便的策略。

更新日期：2020-09-28

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