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Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides

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Abstract

Azide-alkyne click polymerization has become a powerful tool for polymer synthesis. However, the click polymerization between internal alkynes and azides is rarely utilized to prepare functional polymers. In this work, the polymerization reactions of activated internal alkyne monomers of tris(2-butynoate)s (1) with tetraphenylethene-containing diazides (2) were performed in dimethylformamide (DMF) under simple heating, affording four hyperbranched poly(methyltriazolylcarboxylate)s (hb-PMTCs) with high molecular weights (Mw up to 2.4 × 104) and regioregularities (up to 83.9%) in good yields. The hb-PMTCs are soluble in common organic solvents, and thermally stable with 5% weight loss temperatures up to 400 °C. They are non-emissive in dilute solution, but become highly emissive in aggregated state, exhibiting aggregation-induced emission characteristics. The polymers can generate fluorescent photopatterns with high resolution, and can work as fluorescent sensors to detect nitroaromatic explosive with high sensitivity.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 21875152 and 21404077), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 17KJB150034), the Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Guangzhou 510640, China (South China University of Technology) (No. 2019B030301003), and the Priority Academic Program Development of Jiangsu High Education Institutions (PAPD). M. N. L. and Q. Z. Z. thank the financial support from Undergraduate Training Program for Innovation and Entrepreneurship, Soochow University (No. 2018xj032). H. K. L. acknowledges the supports from Jiangsu Planned Projects for Postdoctoral Research Funds (No. 1501023B) and China Postdoctoral Science Foundation (No. 2016M591906).

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Authors and Affiliations

  1. State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Laboratory of Advanced Optoelectronic Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China

    Mu-Ning Lang, Wei-Wen Chi, Qing-Zhen Zhao, Hong-Kun Li & Yong-Fang Li

  2. State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou, 510640, China

    Hong-Kun Li & Ben Zhong Tang

  3. 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, China

    Ting Han & Ben Zhong Tang

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  1. Mu-Ning Lang
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  2. Wei-Wen Chi
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  4. Qing-Zhen Zhao
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  5. Hong-Kun Li
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  7. Yong-Fang Li
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Correspondence to Hong-Kun Li.

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10118_2020_2421_MOESM1_ESM.pdf

Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides

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Lang, MN., Chi, WW., Han, T. et al. Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides. Chin J Polym Sci 38, 1171–1177 (2020). https://doi.org/10.1007/s10118-020-2421-y

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