Two new fluorescent fluorenone azine derivatives: synthesis, physicochemical properties, experimental and theoretical study

• Published in: Journal of the Iranian Chemical Society 2023, Vol.20 (8), p.1975-1983
• Main Authors: Bensegueni, Rafik, Guergouri, Mounia, Kherrouba, Abdelmadjid, Bencharif, Mustapha
• Format: Article
• Language: English
• Subjects: Absorption; Analytical Chemistry; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Density functional theory; Electrochemical analysis; Emission spectra; Fluorescent dyes; Hydrazines; Inorganic Chemistry; Mathematical analysis; Molecular docking; Organic Chemistry; Original Paper; Physical Chemistry; Tyrosinase
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-023-02812-y

Two new fluorescent dyes, (E)-1-(2-hydroxybenzylidene)-2-(9H-fluoren-9-ylidene)hydrazine (FIIS) and (E)-1-(2-hydroxynaphtylidene)-2-(9H-fluoren-9-ylidene)hydrazine (FIIN), were synthesized. Photophysical properties were obtained from electronic absorption and emission spectra in DMF solution. The obtained spectra showed large Stokes shifts (∆λ > 80 nm) that could be beneficial in the biological fluorescence imaging domain. Electrochemical properties were studied by cyclic voltammetry in a Bu 4 NBF 4 (0.1 M)/MeCN organic solution. A theoretical study was carried out using the density functional theory (DFT) and the time-dependent density functional theory (TD-DFT) methods, explaining experimental findings and providing a theoretical support for further investigations. The calculations results were in harmony with experimental ones and were used to estimate the global reactivity descriptors of our molecules. Molecular docking calculations conducted against tyrosinase revealed that the two compounds had lower binding energies (− 7.3 and − 8.4 kcal/mol) compared to the used standard, kojic acid (− 5.4 kcal/mol). This suggests them as possible inhibitors of tyrosinase activity. FIIS and FIIN were screened through Lipinski’s rule of five via the SwissADME server to assess their absorption, distribution, metabolism, and excretion properties. It was found that both molecules fulfilled the related criteria.