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Issue 26, 2020
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A stilbazolium dye-based chromogenic and red-fluorescent probe for recognition of 2,4,6-trinitrophenol in water

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Abstract

The nitroaromatic compounds (NACs) show absorption maxima below 400 nm and their determination using absorption and colour change requires probes with absorption beyond this region. Herein, we report a stilbazolium-based probe DMAS-DP, which undergoes aggregation in HEPES buffer with an absorption maximum at 475 nm (red colour) and these aggregates demonstrate a highly selective and sensitive change in their colour from red to light yellow with 2,4,6-trinitrophenol (TNP). The LOD for the determination of TNP is 100 pM, the lowest in the literature by using visible spectroscopy. Moreover, the aggregates of DMAS-DP emit fluorescence in the red region with a maximum at 615 nm (red under 365 nm light), which is quenched selectively by TNP. 2,4,6-Trinitrotoluene (TNT) and other NACs show insignificant changes in the visible spectrum of the aggregates of DMAS-DP, even when present in excess. Density functional theory (DFT)-based structure optimization studies reveal that the DMAS-DP attains the Z-conformation and its dimethylamino moieties form strong interaction with the protons of TNP and are responsible for the reduced force constant (color). This constitutes the first probe where a stilbazolium dye has been used for constructing a TNP-selective chromogenic and red-fluorescent probe.

Graphical abstract: A stilbazolium dye-based chromogenic and red-fluorescent probe for recognition of 2,4,6-trinitrophenol in water

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Supplementary files

Article information


Submitted
29 Jan 2020
Accepted
29 May 2020
First published
29 May 2020

New J. Chem., 2020,44, 10870-10877
Article type
Paper

A stilbazolium dye-based chromogenic and red-fluorescent probe for recognition of 2,4,6-trinitrophenol in water

S. Dhiman, G. Kumar, V. Luxami, P. Singh and S. Kumar, New J. Chem., 2020, 44, 10870
DOI: 10.1039/D0NJ00489H

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