摘要
铜(I)催化的叠氮-炔烃环加成(CuAAC)点击化学与荧光探针是有机化学科研领域的重要前沿方向,开展相关的教学实验有助于学生创新能力的培养。然而,如何避免使用有毒、有爆炸风险的叠氮类化合物,是本科教学中推广CuAAC点击化学面临的巨大挑战。本文报道了一个改进的适合本科教学的CuAAC点击反应,提高了安全性与趣味性。通过巧妙利用5,7-二甲基四氮唑[1,5-a]嘧啶在溶液中可以互变异构为叠氮化合物的性质,使之与4-乙炔基苯甲醚反应生成三氮唑化合物5,实验中避免了操作叠氮化合物带来的中毒和爆炸风险。实验合成的化合物5可以选择性识别锌离子并作为锌离子荧光探针,具有定量测定锌离子含量的潜力。
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.
作者
付世涛
窦容慧
李馨
郭义娜
张玉苹
熊辉
高晓莉
徐鑫
王龙
Shitao Fu;Ronghui Dou;Xin Li;Yina Guo;Yuping Zhang;Hui Xiong;Xiaoli Gao;Xin Xu;Long Wang(School of Chemistry and Chemical Engineering,Huazhong University of Science and Technology,Wuhan 430074,China)
出处
《大学化学》
CAS
2023年第4期151-159,共9页
University Chemistry
基金
华中科技大学校级教学研究项目(2019028)
华中科技大学自主创新基金(2019kfyXJJS069)
国家自然科学基金(21901079)。
