Synthesis, structural characterization, antimicrobial activities and theoretical investigations of some 4-(4-aminophenylsulfonyl) phenylimino) methyl)-4-(aryldiazenyl) phenol

•The effect of solvent, pH and substituents on enol–keto tautomerism of azo-azomethine dyes•Intramolecular hydrogen bonding, dipole moment changes and their solvatochromism behavior•The substituents on aromatic ring significantly influenced the biological activities.•The results of the calculations show excellent agreement with the experimental value.

The azo-azomethine dyes with a different substitution have been designed from the reaction of 4,4′-diaminodiphenyl sulfone with 2-hydroxy-5-(aryldiazenyl)benzaldehyde. The compounds have been characterized by elemental analysis, Mass, IR, UV–Vis, TGA-DTA and NMR spectroscopy. The solvatochromism behaviors, effects of substitution and pH on the electronic absorption spectra of dyes were evaluated. The in vitro antimicrobial activities were also screened for their potential for antibiotic activities by broth micro dilution method. Also, the optimum molecular geometries, molecular electrostatic potential (MEP), nucleus-independent chemical shift (NICS) and frontier molecular orbitals (FMO), vibrational spectra (IR ) and electronic absorption (UV–Vis) spectra of the title compounds have been investigated with the help of DFT and TDDFT methods with 6-311 ++G(d,p) basis sets and PCM calculations. The results of the calculations show excellent agreement with the experimental value.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide