Solvatochromic and biological studies of new meso-benzodioxole-BODIPY-2-Schiff dye

• Published in: Journal of molecular liquids 2024-11, Vol.413, p.126008, Article 126008
• Main Authors: Piękoś, Patrycja, Maliszewska, Irena Helena, Tursynova, Nurgul, Sokolnicki, Jerzy, Jerzykiewicz, Maria, Bartkiewicz, Stanisław, Filarowski, Aleksander
• Format: Article
• Language: English
• Subjects: A. baumannii; BODIPY; S. aureus; Schiff; Solvatochromism; TD-DFT
• ISSN: 0167-7322
• DOI: 10.1016/j.molliq.2024.126008

[Display omitted] •Synthesis of a new BODIPY dye with bioactive benzodioxole and Schiff base moieties.•Spectral sensitivity of the BODIPY-2-Schiff dye to protic solvents and acid found.•Solvatochromism of the BODIPY-2-Schiff dye elaborated.•DFT and TD-DFT calculations used to interpret experimental findings.•A significant photocidal dye activity against pathogenic S. aureus and A. baumannii. This paper focuses on solvatochromic studies of a new synthesised BODIPY dye with piperonal and ortho-hydroxy aryl Schiff base substituents (BD-2-Schiff). The studied dye has been analysed by spectroscopic and computational techniques to have a deep insight into the impact of the solvents’ polarity and the specific interactions on the dye characteristics. The synthesized dye turns to be sensitive to external specific interactions, caused by protic solvents and acid, which change spectral characteristics of BODIPY-2-Schiff. The calculations by the density functional theory (DFT) and the time-dependent density functional theory (TD-DFT) have been accomplished for the interpretation of the obtained experimental results. The synthesized dye has been evaluated as a photosensitizer for the light induced inactivation of Staphylococcus aureus (S. aureus) and Acinetobacter baumannii (A. baumannii). The synthesized BODIPY dye has shown a significant photocidal activity (above 90 %) against these pathogenic bacteria at low microgram concentrations and excitation with low doses of visible light (0.72 J/cm2; λ = 519 nm).