Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1463-1473.DOI: 10.6023/cjoc202111013 Previous Articles     Next Articles



文乙评a,b, 解正峰a,b,*(), 史天柱a,c, 褚义成a, 周荣贵a, 陶奕杉a, 梁焕敏a, 邱海燕a, 赵云辉d,*()   

  1. a 西南石油大学化学化工学院 油气田应用化学四川省重点实验室 成都 610500
    b 西南石油大学 工业危废处置与资源化利用研究院 成都 610500
    c 茅台学院酿酒工程系 贵州仁怀 564500
    d 湖南科技大学化学化工学院 湖南湘潭 411201
  • 收稿日期:2021-11-15 修回日期:2022-01-12 发布日期:2022-01-27
  • 通讯作者: 解正峰, 赵云辉
  • 基金资助:
    四川省青年科技创新研究团队(2020JDTD0018); 贵州省遵义市科学技术局及茅台学院市校联合科技合作资金(遵市科合HZ字[2021]333号资助项目)

Synthesis of Triazole Functionalized Triphenylamine Cu2+ Fluorescent Probe and Its Application in Detection and HeLa Cells

Yiping Wena,b, Zhengfeng Xiea,b(), Tianzhu Shia,c, Yicheng Chua, Ronggui Zhoua, Yishan Taoa, Huanmin Lianga, Haiyan Qiua, Yunhui Zhaod()   

  1. a Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500
    b Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization, Southwest Petroleum University, Chengdu 610500
    c Department of Brewing Engineering, Moutai Institute, Renhuai, Guizhou 564500
    d School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
  • Received:2021-11-15 Revised:2022-01-12 Published:2022-01-27
  • Contact: Zhengfeng Xie, Yunhui Zhao
  • Supported by:
    Sichuan Youth Science and Technology Innovation Research Team Project(2020JDTD0018); Zunyi Science and Technology Bureau of Guizhou Province and the Maotai Institute Joint Science and Technology Cooperation Fund Project(Zunyi Kehe HZ [2021]333)

A novel fluorescence probe N'-((2-(4'-(diphenyl)-[1,1'-biphenyl]-4-yl)-2H-1,2,3-triazole-4-yl)methylene) hydrazine- 1-thioamide (DBTMC) was designed and synthesized from (4-(diphenylamino)-phenyl)boronic acid, (4-bromophenyl)- 2H-[1,2,3]-triazole-4-carbaldehyde and thiosemicarbazide. DBTMC possessed excellent solvent effect and aggregation effect, and exhibited high selectivity, high sensitivity and rapid response to Cu2+ with detection limit of 4.48×10–8 mol/L. The possible response mechanism was explored through job’s curve, 1H NMR titration, HRMS and density functional theory (DFT) calculations. The test strip prepared with the probe DBTMC solution could be used for quick recognition of Cu2+. DBTMC was applied to HeLa cells to detect Cu2+ and excellent results were achieved, possessing potential application.

Key words: fluorescent probe, copper ion, solvent effect, aggregation effect, HeLa cells