Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin

• Seven novel thiazolyl azo disperse dyes were synthesized and fully characterized.
• The solvatochromic behaviors and coupling component effects on absorption spectra in various solvents were evaluated.
• The absorption spectra of the dyes changed drastically upon acidification.
• The dyes showed good thermal stability for practical applications.

In this study, seven novel thiazolyl azo disperse dyes (6a-g) were synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, and mass spectral techniques. The electronic absorption spectra of the dyes in solvents of different polarities cover a λmax range of 404–512 nm. The absorption properties of the dyes changed drastically upon acidification. This was due to the protonation of the nitrogen in the thiazole ring, which in turn increased the donor-acceptor interplay of the π system in the dyes, and therefore increased the absorption properties of the prepared dyes. Thermal analysis showed that these dyes are thermal stable up to 269 °C. Additionally, the electrochemical behavior of the dyes (6a-g) were investigated using cyclic voltammetric and chronoamperometric techniques, in the presence of 0.10 M tetrabutylammonium tetrafluoroborate, in dimethylsulfoxide, at a glassy carbon electrode. The number of transferred electrons, and the diffusion coefficient were determined by electrochemical methods. The results showed that, for all the dyes, one oxidation peak and two reduction peaks were observed.

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