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Letters in Organic Chemistry

Author(s): Di Yang, Xue-Wen Diao, Ji Liu, Ya-Xin Chen, Ying-Chun Luo and Xiao-Hua Cai*

DOI: 10.2174/1570178619666220511150149

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An Interesting Small Molecule Fluorescent Probe for A Narrow Range (12.5~13) pH and DMSO Detection

Page: [1110 - 1117] Pages: 8

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Abstract

Aims: The development of a sensitive and visual analytical method for detecting and monitoring the change of pH has always attracted great interest because it plays a significant role in chemical reactions, environmental monitoring, and biological systems.

Methods: In this paper, a simple condensation reaction from readily available substrates 2-hydroxy-1- naphthylaldehyde and malononitrile has been carried out to produce probe L with good aggregationinduced luminescence, and its chemical structure was confirmed by 1H NMR, 13C NMR and ESI-MS.

Objective: There is a conjugated system containing two electron-withdrawing cyano groups and an electron- donating hydroxyl group in probe L's molecular structure, exhibiting obvious fluorescence intensity and visible color change through intramolecular charge transfer (ICT) under different pH conditions.

Results: Probe L assumes excellent fluorescence intensity in a DMF/H2O (1:9, v:v) mixed solvent system, and exhibits good reversibility in a very narrow range of pH values (pH = 12.5~13). In addition, probe L can also selectively identify solvent DMSO by the induction of fluorescence quenching.

Conclusion: Probe L can be used for the analysis and visual detection to pH change in DMF/H2O system, and it may also be used as the indicator for the detection and monitoring of trace amounts of DMSO.

Keywords: 2-Hydroxy-1-naphthylformaldehyde, malononitrile, fluorescent probe, pH monitoring, DMSO detection, probe L.

Graphical Abstract

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