CuAAC点击化学法合成三氮唑结构锌离子探针

doi:10.3866/PKU.DXHX202211092

Abstract

Abstract:

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.

Key words: Click chemistry, CuAAC, Fluorescent probe, Azide, Zinc ion

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.

Figures/Tables 13

References 21

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试剂	CAS号	试剂公司	纯度	试剂	CAS号	试剂公司	纯度
乙酰丙酮^*	123-54-6	安耐吉(上海)医药化学有限公司	99%	四水合醋酸锰	6156-78-1	安耐吉(上海)医药化学有限公司	99%
一水5-氨基-1H-四氮唑^*	15454-54-3	上海迈瑞尔生化科技有限公司	99%	四水合氯化亚铁	13478-10-9	上海迈瑞尔生化科技有限公司	98%
4-乙炔基苯甲醚^*	758-60-5	安耐吉(上海)医药化学有限公司	97%	无水三氯化铁	7705-08-0	安耐吉(上海)医药化学有限公司	98%
无水氯化铜^*	7447-39-4	上海阿拉丁生化科技股份有限公司	98%	氯化钴	7646-79-9	上海泰坦科技股份有限公司	98%
L-抗坏血酸钠^*	134-03-2	上海泰坦科技股份有限公司	99%	氯化镍	7718-54-9	上海泰坦科技股份有限公司	99%
噻吩-2-甲酸亚铜^*	68686-76-5	北京百灵威科技有限公司	96%	氯化亚铜	7758-89-6	国药集团化学试剂有限公司(上海沪试)	98%
氯化锌^*	7646-65-7	上海麦克林生化科技股份有限公司	98%	氯化钠	7647-14-5	上海泰坦科技股份有限公司	99%
氘代氯仿^*	865-49-6	上海泰坦科技股份有限公司	99%	氯化钙	10043-52-4	上海泰坦科技股份有限公司	96%
氘代二甲亚砜	2206-27-1	安耐吉(上海)医药化学有限公司	99%

仪器	公司	型号	仪器	公司	型号
熔点仪	仪电物光上海仪分科学仪器有限公司	WRS-1C	荧光光谱仪	Shimadzu, Japan	RF-5301PC
红外光谱仪	赛默飞世尔科技(中国)有限公司	Nicolet iS5	暗箱式紫外分析仪	上海锦岐仪器设备有限公司	ZD-20D
分析天平	上海舜宇恒平科学仪器有限公司	AE224	移液枪	大龙兴创实验仪器(北京)股份公司	0.5–10，20–200 μL
电磁加热搅拌器	上海司乐仪器有限公司	B13-3	旋转蒸发仪	郑州长城科工贸有限公司	R-1001VN
核磁共振仪	Bruker Corporation, Switzerland	AVANCE III 400 MHz

学时安排	合成化合物3	合成化合物5	化合物表征	荧光定性实验	荧光滴定实验
8学时课堂	3.5学时	1.5学时	1学时	1学时	1学时
4学时课堂	–	2学时	1学时	1学时	–

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

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