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Synthesis of octa-benzothiazole functionalized tetraphenylethylene and their explosive sensing properties.

Authors :
Bhusanur, Dnyaneshwar I.
Singh, Prabhat K.
Al Kobaisi, Mohammad
Bhosale, Sidhanath V.
Bhosale, Sheshanath V.
Source :
Journal of Photochemistry & Photobiology A: Chemistry. Jul2024, Vol. 452, pN.PAG-N.PAG. 1p.
Publication Year :
2024

Abstract

[Display omitted] • Synthesis of benzothiazole functionalized tetraphenylethylene (TPE-BTH) is achieved. • TPE-BTH showed turn-off fluorescence response towards TNP and DNP. • TPE-BTH exhibited lower LOD for TNP of 7.28 × 10-8 M. • TPE-BTH displayed lower LOD towards DNP 1.23 × 10-8 M. • Molecular simulation was employed to investigate the interaction between TPE-BTH and TNP and DNP. The detection of nitroaromatic compounds (NACs) such as 2,4,6-trinitrophenol (TNP) and 2,4-dinitrophenol (DNP) is critical for environmental monitoring and security, due to their extensive use in explosives and the associated health risks. However, current methods for detecting these compounds face challenges in sensitivity, specificity, and practicality. In this study, a new benzothiazole functionalized tetraphenylethylene molecular scaffold (TPE-BTH) have been successfully synthesized and characterized for its potential in explosive sensing. The TPE-BTH compound exhibits distinct UV–Visible and fluorescence emission behaviors in different solvent polarities. A remarkable feature of TPE-BTH is its pronounced fluorescence quenching upon the addition of 2,4,6-trinitrophenol (TNP) and 2,4-dinitrophenol (DNP) in a dichloromethane solution, highlighting its sensitivity and potential utility in explosive detection. The detection limits for TNP and DNP were determined to be remarkably low at 7.28 × 10-8 M and 1.23 × 10-8 M, respectively. Through theoretical investigations, we explored the interaction mechanisms between TPE-BTH and TNP, uncovering the roles of internal hydrogen bonding within picric acid and π-π interactions as well as dipole interactions between the molecules. Additionally, 1H NMR was utilized to elucidate the interaction mechanisms between TPE-BTH and TNP. The development of TPE-BTH as a molecular scaffold for NAC detection significantly contributes to the field of explosive sensing and environmental monitoring. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
10106030
Volume :
452
Database :
Academic Search Index
Journal :
Journal of Photochemistry & Photobiology A: Chemistry
Publication Type :
Academic Journal
Accession number :
176357590
Full Text :
https://doi.org/10.1016/j.jphotochem.2024.115580