Premium
Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes
Author(s) -
Vitnik Vesna D.,
Vitnik Željko J.,
Božić Bojan Đ.,
Valentić Nataša V.,
Dilber Sanda P.,
Mijin Dušan Ž.,
Ušćumlić Gordana S.
Publication year - 2017
Publication title -
coloration technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 1472-3581
DOI - 10.1111/cote.12271
Subject(s) - natural bond orbital , intramolecular force , tautomer , chemistry , density functional theory , computational chemistry , basis set , absorption spectroscopy , photochemistry , 2 pyridone , aryl , ultraviolet , materials science , stereochemistry , organic chemistry , physics , alkyl , optoelectronics , quantum mechanics
In this paper, spectroscopic and quantum mechanical investigation of nine 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes was performed, and obtained density functional theory ( DFT ) results were compared with experimental data. The structural and spectroscopic properties of azo‐2‐pyridone dyes were studied by DFT using B3 LYP , CAM ‐B3 LYP , and M06‐2X methods with a 6‐311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time‐dependent DFT calculated and experimental ultraviolet‐visible ( UV ‐vis) absorption spectra are also in good agreement. The effect of electron‐donating – OCH 3 and electron‐withdrawing – NO 2 groups on the structural parameters, vibrational frequencies, UV ‐vis absorption, and natural bond orbital ( NBO ) atomic charges were thoroughly analysed. Vibrational, UV ‐vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo‐pyridone dyes.