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Issue 7, 2020
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Synthesis, photophysics and biomolecule interactive studies of new hybrid benzo-2,1,3-thiadiazoles

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Abstract

Four new hybrid molecules containing benzo-2,1,3-thiadiazole, benzofuran and arylselanyl moieties, named 4,7-bis(3-(arylselanyl)benzofuran-2-yl)benzo[c][1,2,5]thiadiazoles, were designed and synthesized in good yields through an electrophilic cyclization of 4,7-bis((2-methoxyphenyl)ethynyl)benzo[c][1,2,5]thiadiazole 1 and diaryl diselenides 2 using trichloroisocyanuric acid to generate electrophilic arylselanyl species. The photophysical properties of compounds 3a–d were investigated using UV-vis absorption and emission fluorescence analysis. The emission fluorescence analysis showed a yellow-orange region emission. Large Stokes shift values were observed for all new derivatives and attributed to the ICT state and to the electron-substituent properties. The biomolecule-binding DNA and HSA-binding interactions were also investigated by experimental and theoretical methods.

Graphical abstract: Synthesis, photophysics and biomolecule interactive studies of new hybrid benzo-2,1,3-thiadiazoles

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Article information


Submitted
29 Nov 2019
Accepted
14 Jan 2020
First published
15 Jan 2020

New J. Chem., 2020,44, 2768-2780
Article type
Paper

Synthesis, photophysics and biomolecule interactive studies of new hybrid benzo-2,1,3-thiadiazoles

J. S. S. Neto, R. Krüger, R. A. Balaguez, M. G. Fronza, T. V. Acunha, R. S. Oliboni, L. Savegnago, B. A. Iglesias and D. Alves, New J. Chem., 2020, 44, 2768
DOI: 10.1039/C9NJ05932F

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