Reversal in Solvatochromism, enol-imine/keto-amine Tautomerism and (<i>E</i>)-(<i>Z</i>) Photoisomerizations in a Benzylidene Aniline Schiff Base Derivative in Different Solvents.

ABSTRACT: A novel Schiff base, (E)-4-acetyl-N-(4-hydroxy-3-methoxybenzylidene)aniline (abbreviated as ANHMA), was synthesized and characterized using infrared and ¹H- and ¹³C-NMR spectroscopies. Optical properties in different solvents were evaluated using UV-vis absorption spectroscopy. The compound is shown to exhibit both positive and negative solvatochromism with reversal occurring for solvents with E_T(30)~45 (e.g., DMSO). The solvatochromic behavior of the compound was found to be strongly dependent on the hydrogen bond abilities and polarizability of the solvent, the observed reversal in solvatochromism being explained by the change in the dominant solvent effects in non-polar and polar-aprotic solvents (H-bond acceptor ability of th

SUBMITTER: Sıdır I 

PROVIDER: S-EPMC11821250 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature