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

• Published in: Dyes and pigments Vol. 185; p. 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: Journal Article
• Language: English
• Published: Elsevier Ltd 01.02.2021
• Subjects: Benzothiadiazoles; Biomolecule interactions; Electrochemistry; Photophysics; Selenium; Electrochemistry; Biomolecule interactions; Selenium; Photophysics; Benzothiadiazoles
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2020.108910

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.