Photostable coumarin containing azo dyes with multifunctional property

• Published in: Dyes and pigments 2019-04, Vol.163, p.692-699
• Main Authors: Ayare, Nitesh N., Ramugade, Supriya H., Sekar, Nagaiyan
• Format: Article
• Language: English
• Subjects: Antimicrobial activity; Coumarin-azo dyes; Fastness property; Global reactivity descriptors; HOMO-LUMO gap; UPF
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2018.12.050

A series five coumarin azo disperse dyes with thiophene bridge are synthesized using diazotized aniline derivatives which are confirmed by FT-IR, 1H NMR, 13C NMR, and CHN analysis. The dyes are applied on polyester and nylon material. The multifunctional properties (lightfastness, washing fastness, sublimation fastness, K/S, UPF, and antimicrobial activity) of the dyed fabric are determined. The dye 3a (-NO2) show red shifted absorption (649 nm) and blocking 95.5–97.4% of UV radiations with 96% antimicrobial property. The geometries of all the azo dyes are optimized using Density Functional Theory (DFT). The Global Reactivity Descriptors (GRD) are evaluated at the same method of theory. The GRD obtained shows a linear relation with lightfastness and UPF ratings. The antimicrobial activity of all synthesized dyes are determined by AATCC 100 test method and it is correlated with the HOMO-LUMO energy band gap. [Display omitted] •Five coumarin disperse azo dyes with thiophene bridge are synthesized.•3a show red shifted absorption i.e. 649 nm, high UPF and antimicrobial activity. 3a has (-NO2) a strong acceptor with increased pi-conjugation.•They show UPF and antimicrobial property effect on textile fabric.•The lightfastness, UPF and antimicrobial property are correlated with help of Density Functional Theory (DFT).