Citation: Shitao Fu, Ronghui Dou, Xin Li, Yina Guo, Yuping Zhang, Hui Xiong, Xiaoli Gao, Xin Xu, Long Wang. Triazole-based Fluorescent Probe for Zinc Ion Synthesized by CuAAC Click Chemistry[J]. University Chemistry, ;2023, 38(4): 151-159. doi: 10.3866/PKU.DXHX202211092 shu

Triazole-based Fluorescent Probe for Zinc Ion Synthesized by CuAAC Click Chemistry

School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China

Corresponding author: Long Wang, wanglo@hust.edu.cn
Received Date: 29 November 2022

Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) click chemistry and fluorescent probe are hot research topics of organic chemistry. Introducing it into undergraduate laboratory could help to cultivate creativity of students. However, how to avoid the use of azides is a great challenge to promote CuAAC click chemistry in undergraduate education. Herein, we report a modified CuAAC click reaction experiment for undergraduate laboratory teaching, featuring improved safety and interestingness. 5,7-dimethyltetrazolo[1,5-a]pyrimidine can be tautomerized into azide form in solution. Elegantly using this property could achieve the CuAAC reaction between 5,7-dimethyltetrazolo[1,5-a]pyrimidine and 4-acetylene anisole for the generation of triazole compound 5, avoiding the toxicity and explosive risk from the operation of azide compound. The synthesized compound 5 could selectively recognize zinc ions as a fluorescent probe. It is potentially useful for quantitative analysis of zinc ion concentration.
- Click chemistry,
- CuAAC,
- Fluorescent probe,
- Azide,
- Zinc ion
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