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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 2: 718 - 724

DOI: https://doi.org/10.6023/cjoc202205019

Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe

  • Zhihua Chen ,
  • Yan Hu ,
  • Lili Ma ,
  • Ziyi Zhang ,
  • Chuanxiang Liu
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  • Department of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418
* Corresponding author. E-mail:

Received date: 2022-05-13

  Revised date: 2022-09-13

  Online published: 2022-10-10

Supported by

Natural Science Foundation of Shanghai(17ZR1429900); Opening Fund of Shanghai Key Laboratory of Chemical Biology.

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Abstract

In this paper, a novel fluorescent probe A4 for the detection of hypochlorite ions was designed and synthesized using quinoline as a fluorophore and ortho-vinylhydropyridine auxiliary amino group as a recognition site. Experimental studies show that the fluorescent probe has high selectivity for hypochlorite and extreme sensitivity (response time 1.6 s, limit of detection 77.8 nmol/L). After reacting with hypochlorite, the absorption peak of the UV-vis absorption spectrum at 421 nm was blue-shifted, and the color of the solution changed from yellow to colorless. In the fluorescence emission spectrum, the maximum emission peak at 642 nm was quenched, and the fluorescent color changed from orange red to non-fluorescent. The sensing mechanism was confirmed by liquid chromatograph mass spectrometer (LC-MS) analysis and comparison of UV-vis spectra, which involving the ortho-vinylhydropyridine-assisted amido-to-nitroso oxidation reaction. In addition, the A4-loaded test strip was prepared and applied on the detection of hypochlorite. Moreover, the probe showed moderate aggregation-caused quenching (ACQ) with increasing of water content.

Key words： fluorescent probe; hypochlorite ion; oxidation; detection

Cite this article

Zhihua Chen , Yan Hu , Lili Ma , Ziyi Zhang , Chuanxiang Liu . Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 718 -724 . DOI: 10.6023/cjoc202205019

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