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

doi:10.6023/cjoc201809025

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

Articles

一种新型苯并咪唑-酰腙衍生物用于比色和荧光识别F^－和AcO^－

李英俊^a, 赵月^a, 靳焜^b, 刘季红^c, 周晓霞^a, 杨凯栋^a

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 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金（No.20102126）资助项目.

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

Received:2018-09-20 Revised:2018-12-03 Published:2018-12-21
Contact: 10.6023/cjoc201809025 E-mail:chemlab.lnnu@163.com
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No.20102126).

1. A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F^－ and AcO^－.PDF(449KB)

Abstract

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^-.

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

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(4): 1013-1022.

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一种新型苯并咪唑-酰腙衍生物用于比色和荧光识别F^－和AcO^－

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

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一种新型苯并咪唑-酰腙衍生物用于比色和荧光识别F－和AcO－

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

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Metrics

Comments

一种新型苯并咪唑-酰腙衍生物用于比色和荧光识别F^－和AcO^－

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