Electronic structure and spectral and luminescent properties of anti-HIV-active aminophenols

• Published in: Russian physics journal Vol. 54; no. 6; pp. 619 - 626
• Main Authors: Bazyl, O. K., Artyukhov, V. Ya, Mayer, G. V.
• Format: Journal Article
• Language: English
• Published: Boston Springer US 01.11.2011; Springer
• Subjects: Analysis; Condensed Matter Physics; Fluorescence; Hadrons; Heavy Ions; HIV (Viruses); Hydrogen; Hydrogen bonding; Hydroxides; Lasers; Mathematical and Computational Physics; Nuclear Physics; Optical Devices; Optics; Optics and Spectroscopy; Photonics; Physics; Physics and Astronomy; Theoretical; fluorescence; electronically excited states; aminophenol; hydrogen bond
• ISSN: 1064-8887; 1573-9228
• DOI: 10.1007/s11182-011-9661-9

The method of intermediate neglect of differential overlap (INDO) with spectroscopic parameterization is used to calculate the electronic structure and the electronically excited states of substituted o -aminophenols comprising the SO 2 group. It is demonstrated that incorporation of this group into the 2-anilino-4,6-di-tretbutylphenol molecule leads to separation of the π-systems of phenyl rings forming the molecule. The intramolecular hydrogen bonds of various types and the SO 2 group change the charge redistribution between separate fragments of molecules thereby decreasing the donor properties of the phenyl fragments and the acceptor properties of the hydroxyl and amino groups. The influence of the SO 2 group on the absorption and fluorescence spectra is insignificant and consists in a small long-wavelength shift of the absorption band spectrum and insignificant changes of the band intensities. Due to a higher degree of deviation of the molecules from the planar structure after incorporation of this group, the intersystem crossing increases; therefore, the quantum fluorescence yield of sulfosubstitutes is insignificant.