Novel push–pull heterocyclic azo disperse dyes containing piperazine moiety: Synthesis, spectral properties, antioxidant activity and dyeing performance on polyester fibers

• Six novel disperse dyes were synthesized and fully characterized.
• The solvatochromic properties of dyes evaluated in the solvents with different polarity.
• Color fastness of prepared compounds on the polyester fibers was evaluated.
• Antioxidant activities of synthesized dyes were investigated.

Six novel push–pull azo disperse dyes were synthesized via classical azo coupling reaction using 2-amino-thiazolyl derivatives as the diazo components and 1-(4-bromobenzyl)-4-phenylpiperazine as a key coupling intermediate. The structures of the dyes and synthesized intermediate were confirmed by FT-IR, 1H NMR, 13C NMR and UV–vis analyses. The solvatochromic behavior of the dyes was studied in a set of 10 solvents of different polarity and considerable results were obtained. The prepared heterocyclic azo dyes were applied for dyeing polyester fibers and their dyeing properties were studied. The fastness properties of the dyed fabrics such as wash, light and rubbing fastness degrees were measured by standard methods. Investigation of antioxidant activity of compounds was carried out by ferric reducing antioxidant power (FRAP) method. The synthesized dyes exhibited significant antioxidant activities.

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