Synthesis, DNA Interaction and Genotoxic Evaluation of a Photoactive Benzothiadiazole with Potential Application in Photovoltaic Paint

Abstract

A new fluorophore containing 2,1,3-benzothiadiazole unit with alkylated tetrazole terminal groups as electron donors connected through a π-conjugated system of the type (D-π-A-π-D) was synthesized using the Sonogashira coupling reaction with good yields. The genotoxicity of the two intermediate compounds and the final product was evaluated in vitro in consideration of the potential application of the new compound in the chemical production of photovoltaic paints. The new fluorophore did not show significant biological effects in the cell viability test and the comet assay when compared with the intermediate compounds that were obtained synthetically despite the ability to interact with deoxyribonucleic acid (DNA) as demonstrated in circular dichroism assays. Thus, the compound does not show toxic or genotoxic activity, and therefore, it can be applied as a pigment in photovoltaic paint.

Tetrazolo[1,5-a]pyridine-Containing π-Conjugated Systems: Synthesis, Properties, and Semiconducting Characteristics

“…Tetrazole derivatives have been also utilized as components to activate organic reactions and energetic materials . However, the application of tetrazole as an electron-accepting unit in extended π-conjugated molecules is limited, mainly due to the spontaneous elimination of N 2 by explosive decomposition . We expected that the introduction of a fused structure in the construction of tetrazolo­[1,5- a ]­pyridine ( 2 ) would be an effective approach to increase the chemical stability of the tetrazole framework, leading to a creation of a new type of electron-accepting compound.…”