Alkynylselenium-functionalized benzothiadiazoles: Synthesis, photophysics, electrochemistry, and biomolecular interaction studies

We describe herein our results on the synthesis of 4,7-bis((arylselanyl)ethynyl)benzo[c][1,2,5]thiadiazoles 3 by the silver-catalyzed direct selanylation of 4,7-diethynylbenzo[c][1,2,5]thiadiazole 1 with diaryl diselenides. Three new compounds were obtained in good yields using 10 mol% of AgNO3 as a...

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Bibliographic Details
Published in:Dyes and pigments 2021-02, Vol.185, p.108910, Article 108910
Main Authors: Silveira, Carolina H., Fronza, Mariana G., Balaguez, Renata A., Larroza, Allya M.E., Savegnago, Lucielli, Back, Davi F., Iglesias, Bernardo A., Alves, Diego
Format: Article
Language:English
Subjects:
Benzothiadiazoles
Biomolecule interactions
Electrochemistry
Photophysics
Selenium
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Summary:We describe herein our results on the synthesis of 4,7-bis((arylselanyl)ethynyl)benzo[c][1,2,5]thiadiazoles 3 by the silver-catalyzed direct selanylation of 4,7-diethynylbenzo[c][1,2,5]thiadiazole 1 with diaryl diselenides. Three new compounds were obtained in good yields using 10 mol% of AgNO3 as a catalyst under mild reaction conditions. In addition, the preliminary investigation of photophysical properties of the alkynyl derivatives by UV–Vis and steady-state emission fluorescence and electrochemical behavior was also presented. The photophysical properties of the new compounds were determined and experimental and theoretical DNA/HSA binding properties were assessed. •New selenium-functionalized benzothiadiazoles.•Silver-catalyzed direct selanylation of 4,7-diethynylbenzo[c][1,2,5]thiadiazole.•Photophysical properties of the compounds by UV–Vis and steady-state emission fluorescence was evaluated.•Experimental and theoretical DNA/HSA binding properties were assessed.•Synthesized compounds have great interaction with biomacromolecules.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2020.108910