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

Yıldız E., Pepe Y., Erdener D., Karatay A., Boyacıoğlu B., Ünver H., ...More

Journal of Molecular Structure, vol.1295, 2024 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 1295
  • Publication Date: 2024
  • Doi Number: 10.1016/j.molstruc.2023.136731
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Keywords: Benzothiazole, Biological activity, Chromogenic sensing, DFT, Femtosecond transient absorption spectroscopy, Schiff base
  • Çanakkale Onsekiz Mart University Affiliated: Yes

Abstract

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.