Synthesis and spectral properties of new hetarylazo indole dyes

Seferoğlu, Zeynel; Ertan, Nermin

doi:10.1134/s1070428007070160

Cited by 35 publications

(27 citation statements)

References 21 publications

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“…Azo dyes represent the largest group of disperse dyes in textile industry, which are used in the dyeing of synthetic fibres. In addition, some azo dyes were the most widely used in various fields, such as high-technological systems, the coloring of different materials, colored plastics and polymers, biological-medical studies and advanced organic synthesis [12][13][14][15][16][17][18][19][20]. Synthesis and properties of some azopyrimidines and their complexes were described in several publications [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and spectroscopic properties of some new phenylazo-6-aminouracil

Seferoğlu

Ertan

2008

Open Chemistry

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Abstract:In this study, a series of new 5-phenylazo-6-aminouracil dyes were prepared by linking m-,p-nitroaniline, m-,p-chloroaniline, m-,p-anisidine, m-,p-toluidine, m-,p-cyanoaniline, p-ethoxyaniline, p-phenoxyaniline, p-ethylaniline, p-acetamidoaniline, p-acetylaniline, p-carboxyaniline and aniline to 6-aminouracil. The prepared dyes were characterized by UV-vis, FT-IR, 1 H NMR spectroscopic techniques and elemental analysis. The effect of acid and base upon the UV-vis spectra of these dyes were investigated. In addition, the solvatochromic behaviors and substituent effects in various solvents were evaluated. © Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and spectroscopic properties of some new phenylazo-6-aminouracil

Seferoğlu

Ertan

2008

Open Chemistry

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“…In addition, many heterocyclic azo dyes showed large molecular hyperpolarizabilities [9][10][11][12][13][14]. Previously, the synthesis and some structural aspects of some hetarylazoindole dyes have been reported [15][16][17][18][19][20][21][22], and here we report the synthesis and single-crystal X-ray structures of two hetarylazo disperse dyes, which are also supported by the DFT and TD-DFT calculations. There is a relationship between the spectroscopic properties and the molecular structure.…”

Section: Introductionmentioning

confidence: 84%

“…Thiazolyl amines were diazotized using nitrosylsulphuric acid and coupled with 1,2-dimethyl indole using standard procedures [20,21]. Structures of the dyes I and II are given in Fig.…”

Section: Preparation Of Hetarylazoindole Dyesmentioning

confidence: 99%

Synthesis and crystal structures of two hetarylazo indole disperse dyes

et al. 2008

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Two new heterocyclic monoazo disperse dyes were prepared by diazotizing 2-amino-5-methylthiazole and ethyl-1-(2-aminothiazol-4-yl)acetate and coupling with 1,2-dimethyl-indole. Characterization of the dyes was carried out by using UV-vis, FTIR, 1 H-NMR and MS spectroscopic techniques. The structures of the dyes have been determined by single-crystal X-ray diffraction method. The maximum absorption peaks (k max ) in the ultraviolet and visible (UVvis) spectra of the hetarylazoindole dyes have been determined by using the density-functional (DFT method) and time-dependent density-functional (TD-DFT method) theories. Excellent agreement was found between the calculated and experimental k max values.

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“…[25][26][27] It is well-known that mono-azo dyes prepared from enol-and enamine-type coupling components exhibit azo-hydrazone tautomerism. [28][29][30][31][32][33][34][35] Determination of azo-hydrazone tautomerism both in solid state and solution phase is quite interesting both from theoretical and practical standpoints, since the tautomers have different technical properties and dyeing performance. 36 In our previous studies, mono-and bis-azo dyes were synthesized and their structures and spectroscopic properties evaluated.…”

Section: Introductionmentioning

confidence: 99%

“…36 In our previous studies, mono-and bis-azo dyes were synthesized and their structures and spectroscopic properties evaluated. [28][29][30][31][32][33][34][35][37][38][39][40][41][42][43][44][45] Some new phenylazouracil disperse dyes were also synthesized. 34 In these studies, azo-hydrazone tautomerism was investigated for the dyes, both in the solid state and solution phase.…”

Section: Introductionmentioning

confidence: 99%