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Fluorescence Quenching and Electron Transfer Dynamics of a Thiophene-Substituted 1,3,4-Oxadiazole Derivative with Nitroaromatic Compounds.

Created on 02 May 2025

Authors

Praveenakumara A Valmiki, M S Thippeswamy, Lohit Naik, C V Maridevarmath, G H Malimath

Published in

Journal of fluorescence. May 02, 2025. Epub May 02, 2025.

Abstract

This study investigates the fluorescence quenching behavior of a newly synthesized thiophene-substituted 1,3,4-oxadiazole derivative, 2-(4-(4-vinyl phenyl)phenyl)-5-(5-(4-vinyl phenyl)thiophene-2-yl)-1,3,4-oxadiazole (TSO), in the presence of various nitroaromatic compounds (NACs), including 2-nitrotoluene, 4-nitrotoluene, nitrobenzene, and picric acid (2,4,6-trinitrophenol). The interactions were examined in an ethanol medium at room temperature using steady-state and time-resolved fluorescence spectroscopy. Steady-state fluorescence analysis revealed a non-linear Stern-Volmer (SV) plot exhibiting positive deviation, while time-resolved measurements displayed a linear relationship. To interpret these findings, ground-state complex formation and the sphere-of-action static quenching models were applied. The study determined key quenching parameters, including the Stern-Volmer constant, quenching rate constant, static quenching constant, and sphere-of-action radius. Notably, fluorescence quenching efficiency increased with the number of NO2 groups in the NACs.Electrochemical analysis, complemented by Density Functional Theory (DFT) calculations, confirmed that electron transfer was the primary quenching mechanism. Furthermore, binding site analysis demonstrated a 1:1 binding stoichiometry between TSO and NACs, with picric acid exhibiting the highest binding affinity. Given the growing interest in fluorescence-based sensing approaches, these findings contribute valuable insights into the development of advanced sensors for detecting nitroaromatic pollutants and explosive residues.

PMID:
40314891
Bibliographic data and abstract were imported from PubMed on 02 May 2025.

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