Improvement of theoretical UV-Vis spectra calculations by empirical solvatochromic parameters: Case study of 5-arylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones

Jelena M Lađarević; Bojan Đ Božić; Vesna D Vitnik; Luka R Matović; Dušan Ž Mijin; Željko J Vitnik

doi:10.1016/j.saa.2022.120978

Improvement of theoretical UV-Vis spectra calculations by empirical solvatochromic parameters: Case study of 5-arylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones

Spectrochim Acta A Mol Biomol Spectrosc. 2022 May 5:272:120978. doi: 10.1016/j.saa.2022.120978. Epub 2022 Feb 3.

Authors

Jelena M Lađarević¹, Bojan Đ Božić², Vesna D Vitnik³, Luka R Matović⁴, Dušan Ž Mijin⁵, Željko J Vitnik³

Affiliations

¹ Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Serbia. Electronic address: jmirkovic@tmf.bg.ac.rs.
² Institute of Physiology and Biochemistry "Ivan Djaja", Faculty of Biology, University of Belgrade, Studentski trg 16, Belgrade, Serbia.
³ Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 12-16, Belgrade, Serbia.
⁴ Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Serbia.
⁵ Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Serbia.

PMID: 35151162
DOI: 10.1016/j.saa.2022.120978

Abstract

In order to improve the performance of theoretical UV-Vis spectra predictions, a theoretical and experimental study of solvatochromic properties of ten azo pyridone dyes has been performed. For quantitative estimation of intermolecular solvent-solute interactions, a concept of the linear solvation energy relationships has been applied using Kamlet-Taft and Catalán models. Theoretical UV-Vis spectra for all dyes have been calculated using four TD-DFT methods in nine different solvents with the aim to define the most reliable model. Finally, new polylinear equations for more accurate theoretical prediction of UV-Vis maxima are developed using empirical Kamlet-Taft and Catalán solvent parameters as additive corrections for specific and nonspecific solvent-solute interactions.

Keywords: Azo dye; DFT calculation; Linear solvation energy relationship; Pyridone; Solvatochromism; UV–Vis spectra prediction.

MeSH terms

Azo Compounds*
Coloring Agents
Pyridones*
Solvents

Substances

Azo Compounds
Coloring Agents
Pyridones
Solvents
2-hydroxypyridine