Abstract
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated.
Highlights
The growing interest in heterocyclic azo dye chemistry is focused on designing new synthetic approaches to these materials, theoretical calculations, and applications in various industrial fields
The results of the present study may point that the novel products could be useful as synthetic precursors for azo- and azomethine ligands or polymethine dyes which may be suitable for both electronic and optical applications
We report the synthetic strategies for preparation of a series of novel functionalized acyclic and heterocyclic azo dyes and dye precursors comprising conjugate enaminones and/or enaminonitrile moieties
Summary
The growing interest in heterocyclic azo dye chemistry is focused on designing new synthetic approaches to these materials, theoretical calculations, and applications in various industrial fields. Functional dyes with special finishing capabilities is currently an area of active research [17]. Many researchers have explored in the field of simultaneous dyeing and functional finishing of textiles, such as the simultaneous dyeing and durable press finishing of cotton [25,26,27], the combination of dyeing and durable press finishing of silk [28,29], the simultaneous dyeing and finishing of wool [30], as well as the simultaneous dyeing and antimicrobial finishing of acrylic fabrics [31]. Other reports concerning antimicrobial functional finishing of synthetic fabrics via treatment with either
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