4.6 Article

Chromogenic sensing, biological, and optical properties of Schiff bases of 2-amino-6-methoxybenzothiazole

Journal

JOURNAL OF MOLECULAR STRUCTURE
Volume 1295, Issue -, Pages -

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ELSEVIER
DOI: 10.1016/j.molstruc.2023.136731

Keywords

Benzothiazole; Schiff base; Chromogenic sensing; Biological activity; Femtosecond transient absorption spectroscopy; DFT

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In this study, a new series of Schiff base benzothiazole derivatives were synthesized and their chemical properties, biological activities and sensing capabilities were investigated. The compounds exhibited excellent fluorescence, chromogenic and spectroscopic sensing properties towards various anions. Moreover, they showed binding, cleavage and antioxidant activity towards DNA.
In this study, a new series of Schiff base benzothiazole derivatives were synthesized and their structures were characterized by elemental analysis, FTIR, UV-VIS and NMR spectroscopy. The biological, sensory and photophysical properties of the benzothiazole derivatives were investigated. The sensing properties of the compounds were investigated UV-VIS spectroscopically, calorimetrically and theoretically. All compounds showed colorimetric, fluorometric and spectroscopic sensor properties for F-, CN-, AcO-, H2PO4- and OH- anions. Furthermore, DNA binding, DNA cleavage and antioxidant activities of compounds 1-4 were investigated. All compounds affected pBR322 DNA both hydrolytically and oxidatively, interacted with DNA in electrostatic mode, and also compounds 1 and 2 exhibited antioxidant activity close to standard BHT. In addition, the effects of electron donating and accepting substituents on the emission properties and charge transfer dynamics were investigated by fluorescence and femtosecond transient absorption spectroscopy measurements, respectively. According to fluorescence measurements, compounds 3 and 4 showed emission signal, while compounds 1 and 2 showed fluorescence quenching and weaker emission signal.

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