Citation: Li Yingjun, Zhao Yue, Jin Kun, Liu Jihong, Zhou Xiaoxia, Yang Kaidong. A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F^- and AcO^-[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1013-1022. doi: 10.6023/cjoc201809025 shu

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

Li Yingjun ^a,, ,
Zhao Yue ^a ,
Jin Kun ^b ,
Liu Jihong ^c ,
Zhou Xiaoxia ^a ,
Yang Kaidong ^a

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

Corresponding author: Li Yingjun, chemlab.lnnu@163.com
Received Date: 20 September 2018
Revised Date: 3 December 2018
Available Online: 21 April 2019
Fund Project: Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126)the Natural Science Foundation of Liaoning Province 20102126

Figures(11)

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 (K_a) 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^-.
- benzimidazole-hydrazone,
- anion,
- naked-eye recognition,
- colorimetric and fluorescent probe
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沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

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