Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition
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The copper-catalyzed and metal-free azide-alkyne click polymerizations have become efficient tools for polymer synthesis. However, the 1,3-dipolar polycycloadditions between internal alkynes and azides are rarely employed to construct functional polymers. Herein, the polycycloadditions of dibutynoate (1) and tetraphenylethene-containing diazides (2) were carried out at 100 °C for 12 h under solvent- and catalyst-free conditions, producing soluble poly(methyltriazolylcarboxylate)s (PMTCs) with high molecular weights in high yields. The resultant polymers were thermally stable with 5% weight loss temperatures up to 377 °C. The PMTCs showed aggregation-induced emission (AIE) properties. They could work as fluorescent sensors for detecting explosive with high sensitivity, and generate two-dimensional fluorescent photopatterns with high resolution. Furthermore, their triazolium salts could be utilized for cell-imaging applications.
KeywordsSolvent- and catalyst-free polycycloaddition Aggregation-induced emission Photopattern Cell imaging
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This work was partially 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), and the Priority Academic Program Development of Jiangsu High Education Institutions (PAPD). H. K. Li acknowledges the financial supports from Jiangsu Planned Projects for Postdoctoral Research Funds (No. 1501023B) and China Postdoctoral Science Foundation (No. 2016M591906).
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