Synthesis, characterization, spectroscopic properties and computational studies of some new azo dyes derived from 5-chloro-8-hydroxy quinoline

Abstract

Purpose

The purpose of this study, 3-aminopyridine, 8-aminoquinoline and some new synthesized 2-aminobenzothiazoles were diazotized with nitrosyl sulfuric acid and subsequently coupled with 5-chloro-8-hydroxy quinoline to synthesize the corresponding heteroarylazo dyes 6–13.

Design/methodology/approach

The structures of dyes were characterized by mass, Fourier transform infra red, ¹H proton nuclear magnetic resonance and ultra violet-visible spectroscopic techniques. Absorption spectra of the dyes were measured in acetic acid, ethanol, chloroform, acetonitrile, dimethyl formamide and dimethyl sulfoxide and correlated with the nature of the solvents and substituents. The effects of varying pH on the absorption wavelengths of the azo dyes were also studied. In addition, the acidity constants (pKa) of the dyes were 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 to compare the energies of proposed azo and hydrazone tautomers of the dyes.

Findings

The results showed that the withdrawing chloro groups on the diazo moiety have significant influence (red shift) on the electron absorption spectra of these dyes. In addition, introducing electron withdrawing chloro groups into the benzothiazoles moiety increased the acidic character of dyes.

Originality/value

The synthesized 7-hetroarylazo-5-chloro-8-hydroxy quinoline dyes are new members in the 8-hydroxyquinoline azo dyes family, where very few details regarding the synthesis of such dyes are reported before in the literature. They are unique in terms of synthesis, spectral properties and DFT calculations.

Citation

Ashouri Mirsadeghi, F., Moradi Rufchahi, E. and Zarrabi, S. (2023), "Synthesis, characterization, spectroscopic properties and computational studies of some new azo dyes derived from 5-chloro-8-hydroxy quinoline", Pigment & Resin Technology, Vol. 52 No. 5, pp. 601-613. https://doi.org/10.1108/PRT-02-2022-0022