The Effects of Terminal Groups in 4–Aminoazobenzene and Disperse Dyes Related Thereto

In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH 3 and electronwithdrawing -NO 2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.

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“…Azo compounds are one of the most important molecules in the fields of dyes, pigments, and advanced materials [1][2][3][4].…”

Section: Society Of Dyers and Colouristsmentioning

confidence: 99%

Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes

Vitnik

Božić

et al. 2017

Coloration Technology

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“…[1][2][3][4][5][6] The success of azo colorants is due to the simplicity of their synthesis by diazotization and azo coupling, to the almost innumerable possibilities presented by variation on the diazo compounds and coupling components, to the generally high molar extinction coefficient and to the medium to high light and wet fastness properties. [1][2][3][4][5][6] The success of azo colorants is due to the simplicity of their synthesis by diazotization and azo coupling, to the almost innumerable possibilities presented by variation on the diazo compounds and coupling components, to the generally high molar extinction coefficient and to the medium to high light and wet fastness properties.…”

Section: Introductionmentioning

confidence: 99%

“…Absorption spectra of the arylazo pyridone dyes(1)(2)(3)(4)(5)(6)(7)(8)(9) in N,N-dimethylacetamide.…”

mentioning

confidence: 99%

Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones

Alimmari¹,

Marinković²,

Mijin³

et al. 2010

JSCS

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A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1 H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.

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“…This is expected for a system in which the excited state is more polar than the ground state [40,41].…”

Section: Absorption Spectramentioning

confidence: 89%

Novel azo disperse dyes derived from aminothiophenes: Synthesis and UV–visible studies

Abd‐El‐Aziz

Afifi

2006

Dyes and Pigments

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The Effects of Terminal Groups in 4–Aminoazobenzene and Disperse Dyes Related Thereto

Cited by 96 publications

References 36 publications

Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes

Experimental and theoretical insight into the electronic properties of 4‐aryl‐5‐arylazo‐3‐cyano‐6‐hydroxy‐2‐pyridone dyes

Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones

Novel azo disperse dyes derived from aminothiophenes: Synthesis and UV–visible studies

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