Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes
نویسندگان
چکیده
UNLABELLED BACKGROUND A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. RESULTS The structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. CONCLUSIONS The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.
منابع مشابه
Synthesis, Characterization, Tautomeric Structure and Solvatochromic Behavior of Novel 4-(5-Arylazo-2-Hydroxystyryl)-1-Methylpyridinium Iodide as Potential Molecular Photoprobe
A novel series of the title compound 4-(5-arylazo-2-hydroxystyryl)-1-methylpyridinium iodide 6 has been synthesized via condensation reactions of the arylazosalicylaldehyde derivatives 4a-i with 1-methyl-picolinium iodide 5. The structures of the new arylazo compounds were characterized by ¹H NMR, IR, mass spectroscopy, as well as spectral and elemental analyses. The electronic absorption spect...
متن کاملSynthesis of Some New Azo Disperse Dyes and Investigation of Their Solvatochromic Effect
The synthesis and properties of new monoazo dyes derived from the diazonium salts of paminobenzoic acid, 3-trifluoromethyl aniline , 4-trifluoromethyl aniline are considered .Theprepared compounds were characterized by UV-Visible , FT-IR and H NMR spectroscopictechniques . The effect of varying solvent upon the absorption ability of p-amino benzoic acidcoupled with 4,4 —diethyl aniline , anilin...
متن کاملNovel Aza-Substituted Benzothiazol and 1,2,4-Triazol Cyanine Dyes: Synthesis, Characterization and Properties
Series of novel dichromophoric cyanine dyes based on 2-aminobenzothiazoles and 3-amino-1,2,4 -triazole have been synthesized in high yields. All the dyes have been classified as disperse dyes. Besides their electronic spectroscopic properties, high dye-uptakes on polyester, excellent fastness properties, highly extinction coefficients, and broad solvatochromic effects have been observed in thes...
متن کاملBromination and diazo-coupling of pyridinethiones; microwave assisted synthesis of isothiazolopyridine, pyridothiazine and pyridothiazepines.
Isothiazolopyridines, pyridothiazines and pyridothiazepines are important compounds that possess valuable biological activities. This paper reports on the synthesis of these compounds using both conventional chemical methods and modern microwave techniques. 3-Bromo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide, 5-arylazo-6-hydroxy-4-methyl-2-thioxo-1,2-dihydropyridine-3-carboxam...
متن کامل5-Arylazo-2,2 ́-bithiophenes: a Novel Promising Series of NLO Chromophores
The synthesis of 5-arylazosubstituted bithiophenes and their UV-visible, solvatochromic and nonlinear optical properties (NLO) are described. In agreement with the solvatochromic data and also with the second-order molecular NLO characterization, the new donor-acceptor systems could find application as suitable solvatochromic probes and also as new NLO materials.
متن کامل