Synthesis, spectroscopic evaluation and density functional theory calculations of some new azo dyes based on 5-chloro-8-hydroxyquinoline

Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, Lahijan Branch, Islamic Azad University, Lahijan, Iran

2 Department of chemistry, Faculty of Sciences, Islamic azad University, Lahijan Branch, Lahijan, Iran

Abstract

In this study, two 2-aminobenzothiazole derivatives were prepared by the reaction of appropriate substituted anilines with potassium thiocyanate in acetic acid followed by mild cyclization oxidation reaction with bromine at room temperature. Then, 2-aminobenzothiazole and each of the two synthesized amines were diazotized with nitorsyl sulfuric acid and coupled with 5-chloro-8-hydroxy quinoline to prepare corresponding heteroarylazo dyes. Their solvatochromism was evaluated in different solvents. The effects of acid and base on the absorption maximum wavelengths of the compounds were also studied. From the optical spectra, in each case, the isosbestic points indicate that the two species are in equilibrium. For all of the compounds under investigation, the dependence of the absorbance on the pH value gives sigmoid curves. The acidity constants (pKa) of the dyes were also determined using the spectrophotometric method in an ethanol-water mixture (80:20, v/v) at 20-23°C. Besides, density functional theory (DFT) calculations were carried out in order to compare the energies of proposed azo and hydrazone tautomers of the dyes.

Keywords

References

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