Synthesis and solvatochromism of heterocyclic bichromophoric dyes derived from 2‐aminothiazole

Abstract

Purpose

The purpose of this paper is to investigate some novel bis‐hetaryl dyes containing both azo and azo methine chromophores on their molecular structures: two series of different molecular structures of these dyes were synthesised. The spectral characteristics and the relationships between colour and constitution of these dyes in solvents with different polarities were systematically investigated and discussed.

Design/methodology/approach

A series of novel bichromophoric dyes containing azo and azomethine chromophores were synthesized using two kinds of reaction routes. 2‐amino‐4‐(p‐substituted) phenyl‐thiazole derivatives, which are coupling components, were subjected to diazotisation with aniline derivatives and then to condensation with benzaldehyde derivatives. By exchanging the synthesis route, two series of bichromophoric dyes could be obtained.

Findings

The maximum absorption wavelengths of the obtained dyes would be attributed to the higher bathochromic shift in basic organic solvent with high polarity, such as dimethylformamide, as compared with the solvent with low polarity, such as chloroform.

Research limitations/implications

In the present study, a series of novel bichromophoric dyes were synthesized by means of two‐step pathway. In addition, the effects of substituent on the primary aromatic amine and on benzaldehyde moieties will also be discussed.

Practical implications

This novel synthesis method of the thiazole ring would lead to the formation of 2‐amino‐4‐(p‐substituted)phenyl‐thiazole with heteroaromatic coupling component position at C‐5, and consequently would produce the heteroaromatic diazo component at C‐2 for the preparation of the heteroaryl diazo dyes.

Originality/value

In this paper, the bichromophoric dyes obtained by different synthesis routes would indicate that the effect of solvent polarity should be responsible for the bathochromic shifts of the dyes.

Citation

Yen, M.S. (2012), "Synthesis and solvatochromism of heterocyclic bichromophoric dyes derived from 2‐aminothiazole", Pigment & Resin Technology, Vol. 41 No. 4, pp. 216-222. https://doi.org/10.1108/03699421211242446