Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1013-1022.DOI: 10.6023/cjoc201809025 Previous Articles     Next Articles

Special Issue: 荧光探针-生物传感合辑 有机超分子化学合辑



李英俊a, 赵月a, 靳焜b, 刘季红c, 周晓霞a, 杨凯栋a   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 大连理工大学精细化工国家重点实验室 大连 116012;
    c 大连理工大学化学分析测试中心 大连 116023
  • 收稿日期:2018-09-20 修回日期:2018-12-03 发布日期:2018-12-21
  • 通讯作者: 李英俊
  • 基金资助:


A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F and AcO

Li Yingjuna, Zhao Yuea, Jin Kunb, Liu Jihongc, Zhou Xiaoxiaa, Yang Kaidonga   

  1. a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012;
    c Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian 116023
  • Received:2018-09-20 Revised:2018-12-03 Published:2018-12-21
  • Contact: 10.6023/cjoc201809025
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No.20102126).

A novel benzimidazole-hydrazone derivative,N'-(2-hydroxy-1-naphthyl)methylene-2-[2-(4-methylphenylsulfonyl-methyl)-1H-benzoimidazol-1-yl]acetohydrazide (L), was synthesized and characterized by IR, 1H NMR, 13C NMR, HRMS and elemental analysis. The recognition properties of L for anions were studied by naked eye, ultraviolet-vis and fluorescence spectroscopy. The results showed that the color of the solution changes from colorless to bright yellow upon addition of F-, AcO- and H2PO4- to the CH3CN solution of compound L. The solution of L emitted yellow fluorescence after the addition of F- and AcO- under the UV lamp (λ=365 nm). It indicated that compound L can be used as a probe for the naked eye to recognize F-, AcO- and H2PO4-. The experimental results of UV and fluorescence spectroscopy showed that the probe L can recognize F- and AcO- with high selectivity and sensitivity. The binding constants (Ka) of probe L to F- and AcO- were 4.25×103 and 2.96×104 L·mol-1, respectively. The detection limits (DL) were 3.63×10-7 and 8.51×10-8 mol·L-1, respectively. The stoichiometry of complexation between L and F-/AcO- was 1:1, which was supported by the Job's plot and density functional theory (DFT) calculations. The mechanism of binding of L with F-/AcO- was established by 1H NMR titration. The results showed that compound L can be used as a colorimetric and fluorescent probe for detecting F- and AcO-.

Key words: benzimidazole-hydrazone, anion, naked-eye recognition, colorimetric and fluorescent probe