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无金属催化的活性叠氮化物与炔烃的多环加成反应制备多功能聚三唑:聚集诱导发光、爆炸物检测、荧光图案化及光折射

Metal-Free Poly-Cycloaddition of Activated Azide and Alkynes toward Multifunctional Polytriazoles: Aggregation-Induced Emission, Explosive Detection, Fluorescent Patterning, and Light Refraction.

作者信息

Wu Yongwei, He Benzhao, Quan Changyun, Zheng Chao, Deng Haiqin, Hu Rongrong, Zhao Zujin, Huang Fei, Qin Anjun, Tang Ben Zhong

机构信息

State Key Laboratory of Luminescent Materials and Devices, 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, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong.

出版信息

Macromol Rapid Commun. 2017 Sep;38(18). doi: 10.1002/marc.201700070. Epub 2017 May 11.

DOI:10.1002/marc.201700070
PMID:28493513
Abstract

The metal-free click polymerization (MFCP) of activated alkynes and azides or activated azide and alkynes have been developed into powerful techniques for the construction of polytriazoles without the obsession of metallic catalyst residues problem. However, the MFCP of activated azides and alkynes is rarely applied in preparation of functional polytriazoles. In this paper, soluble multifunctional polytriazoles (PIa and PIb) with high weight-average molecular weights (M up to 32 000) are prepared via the developed metal-free poly-cycloaddition of activated azide and alkynes in high yields (up to 90%). The resultant PIa and PIb are thermally stable, and show aggregation-induced emission characteristics, enabling their aggregates to detect explosives with superamplification effect. Moreover, thanks to their containing aromatic rings and polar moieties, PIa and PIb exhibit high refractive indices. In addition, they can also be cross-linked upon UV irradiation to generate 2D fluorescent patterning due to their remaining azide groups and containing ester groups. Thus, these multifunctional polytriazoles are potentially applicable in the optoelectronic and sensing fields.

摘要

活化炔烃与叠氮化物或活化叠氮化物与炔烃之间的无金属点击聚合(MFCP)已发展成为构建聚三唑的强大技术,无需担心金属催化剂残留问题。然而,活化叠氮化物与炔烃的MFCP很少应用于功能性聚三唑的制备。本文通过开发的活化叠氮化物与炔烃的无金属多环加成反应,高产率(高达90%)制备了具有高重均分子量(M高达32000)的可溶性多功能聚三唑(PIa和PIb)。所得的PIa和PIb具有热稳定性,并表现出聚集诱导发光特性,使其聚集体能够以超放大效应检测爆炸物。此外,由于PIa和PIb含有芳香环和极性基团,它们具有高折射率。此外,由于它们剩余的叠氮基团和含有酯基,在紫外线照射下它们还可以交联以产生二维荧光图案。因此,这些多功能聚三唑在光电和传感领域具有潜在的应用价值。

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