Citation: Wei-Wen Chi, Rong-Yuan Zhang, Ting Han, Jian Du, Hong-Kun Li, Wei-Jie Zhang, Yong-Fang Li, Ben Zhong Tang. Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition[J]. Chinese Journal of Polymer Science, ;2020, 38(1): 17-23. doi: 10.1007/s10118-019-2316-y shu

Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition

a.
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
b.
Department of Urology, The First Affiliated Hospital of Soochow University, Suzhou 215006, China
c.
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

Corresponding author: Hong-Kun Li, hkli@suda.edu.cn Wei-Jie Zhang, wj539@163.com Ben Zhong Tang, tangbenz@ust.hk
Received Date: 17 April 2019
Revised Date: 6 June 2019
Available Online: 3 September 2019

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.
- Solvent- and catalyst-free polycycloaddition,
- Aggregation-induced emission,
- Photopattern,
- Cell imaging
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