Solvatochromic analysis and DFT computational study of an azomaleimide derivative

Solvatochromic behavior of (E)-4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-N-(4-(phenyldiazenyl)phenyl) benzamide (MIAz) was investigated using electronic absorption spectra in solvents with different polarities. The electronic structure of MIAz has been detailed by DFT method at B3LYP/6-311 ++G(d,p) level of theory. The changes in the electronic absorption band positions as a function of the solvent polarity were discussed using different solvent parameters such as Kamlet-Taft, Lippert-Mataga methods, four-parameter Catalan and Laurence polarity scales. The theoretical electronic absorption spectra of MIAz were computed by time-dependent density functional theory at B3LYP/6-311 ++G(d,p) level. The computed absorption spectral data of MIAz are in good agreement with the experimental results. The HOMO-LUMO energy gap, molecular electrostatic potential and solvent accessible surface for MIAz were also performed at 6-311 ++G(d,p) level of theory. (C) 2017 Elsevier B.V. All rights reserved.