A combined experimental and TD-DFT investigation of three disperse azo dyes having the nitroterephthalate skeleton

Deshmukh, Mininath S.; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2013.10.035

Cited by 32 publications

(9 citation statements)

References 26 publications

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“…Dye production includes thousands of marketed azo and styryl dyes used in textile dyeing, paper printing, photography, pharmaceutical, food, cosmetics, and petroleum product industries [1,2]. Investigations on disperse styryl and azo dyes having aromatic heterocycles are very important because they have shown brilliant color and chromophoric strength, excellent light, color, washing and sublimation fastness as well as high level-dyeing property in the dyestuff industry.…”

Section: Introductionmentioning

confidence: 99%

Disperse styryl and azo dyes for polyester and nylon fibre: Synthesis, optical properties having the 1,2,4-triketo naphthoquinone skeleton

2015

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The azo and styryl disperse dyes were synthesized by using 2-hydroxy-1,4-naphthoquinone (Lawsone) 1 and different substituted aromatic anilines and/or aldehydes. The structures of the dyes were confirmed using FT-IR, 1 H-NMR, MS, and HRMS spectral analysis. The dyes displayed a broad absorption maximum in the visible region between 426 and 490 nm. The present paper deals with the application of azo and styryl disperse dyes on polyester and nylon fiber, color characteristics, and fastness properties. The color strength (K/S value) has been found to be very good in all dyed polyester samples. The color fastness with respect to light exposure, washing, and rubbing was quite satisfactory for all dyed polyester compared to the nylon samples.

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Section: Introductionmentioning

confidence: 99%

Disperse styryl and azo dyes for polyester and nylon fibre: Synthesis, optical properties having the 1,2,4-triketo naphthoquinone skeleton

2015

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“…The literature contains many reports on the successful application of DFT to azo dyes (16)(17)(18)(19)(20)(21)(22)(23). In this study, a series of azo dyes containing an imine group were synthesised and characterised using both spectroscopy and Kohn-Sham DFT (24) method.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Özkınalı¹,

Çavuş²,

Sakin³

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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In this study, azo dyes containing an imine group were synthesised by coupling phydroxybenzylidene aniline with the diazonium salts of p-toluidine, 4-aminophenol, aniline, pchloroaniline, p-fluoroaniline and p-nitroaniline. The compounds were characterised by melting point, elemental, UV-Vis and IR analyses as well as 1 H-NMR and 13 C-NMR spectroscopies. Moreover, the experimental data were supplemented with density functional theory (DFT) calculations. The experimental data on FT-IR and UV-Vis spectra of the compounds were compared with theoretical results. The DFT calculations were performed to obtain the ground state geometries of the compounds using the B3LYP hybrid functional level with 6-311++g(2d,2p) basis set. Frontier molecular orbital energies, band gap energies and some chemical reactivity parameters, such as chemical hardness and electronegativity, were calculated and compared with experimental values. A significant correlation was observed between the dipole moment and polarities of the solvents and the absorption wavelength of the compounds.

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“…On such dyes some light fastness-structure correlations indicate that the fastness increases as the substituent in the para position is made more electronegative [70] and second substituent in the ortho position have a profound effect on light fastness. Light fastness increases with increasing electron-donating power of the ortho substituents to the azo linkage [71]. The dye 4c and 5c is an identical example for this criteria (Scheme 1).…”

Section: Fastness Propertiesmentioning

confidence: 94%

Benzophenone based photostable fluorescent monoazo disperse dyes: Synthesis, AIE, viscosity, UPF and TD-DFT study

2020

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A combined experimental and TD-DFT investigation of three disperse azo dyes having the nitroterephthalate skeleton

Cited by 32 publications

References 26 publications

Disperse styryl and azo dyes for polyester and nylon fibre: Synthesis, optical properties having the 1,2,4-triketo naphthoquinone skeleton

Disperse styryl and azo dyes for polyester and nylon fibre: Synthesis, optical properties having the 1,2,4-triketo naphthoquinone skeleton

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Benzophenone based photostable fluorescent monoazo disperse dyes: Synthesis, AIE, viscosity, UPF and TD-DFT study

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