State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou, 510640, China.
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, Department of Chemical and Biological Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China.
Macromol Rapid Commun. 2020 Jun;41(12):e2000179. doi: 10.1002/marc.202000179. Epub 2020 May 28.
As an important nitrogen source, isocyanides have been involved in numerous organic reactions. As a result, many complicated compounds have been successfully synthesized through isocyanide chemistry. However, compared with its popular research in organic reactions, the application of isocyanides in polymerization is less investigated. In this work, a new polymerization based on isocyanide monomers is established. By simply mixing diisocyanoacetates and dialdehydes in the presence of a catalytic system of CuCl/PPh /organobase in dichloromethane at room temperature readily produces soluble and thermally stable oxazoline-containing polymers with moderate weight-averaged molecular weights (M up to 11 200) in excellent yields (up to 97%) after 6 h. Furthermore, introducing the tetraphenylethene moiety into the main chains endows the resultant polymers with aggregation-induced emission, which can function as fluorescent probes for Fe ion detection with high sensitivity and selectivity. This work not only enriches the family of isocyanide-based polymerizations but also provides an efficient tool for the preparation of functional heterocycle-containing polymers.
作为一种重要的氮源，异氰化物已广泛应用于多种有机反应。因此，通过异氰化物化学可以成功合成许多复杂的化合物。然而，与在有机反应中的广泛研究相比，异氰化物在聚合反应中的应用研究较少。在这项工作中，建立了一种基于异氰化物单体的新聚合方法。通过简单地将二异氰酸酯和二醛混合，在室温下的催化体系（CuCl/PPh3/有机碱）存在下，在二氯甲烷中很容易得到可溶性和热稳定的含恶唑啉聚合物，产率高达 97%（6 小时后），数均分子量（Mw）高达 11200。此外，将四苯乙烯部分引入主链，赋予所得聚合物聚集诱导发光，可作为 Fe 离子检测的荧光探针，具有高灵敏度和选择性。这项工作不仅丰富了基于异氰化物的聚合方法，而且为制备功能性含杂环聚合物提供了一种有效工具。
