Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes
AuthorsAlimmari, Adel SA
Valentić, Nataša V.
Article (Published version)
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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, H-1 NMR and C-13 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.
Keywords:Arylazo pyridone dyes / Tautomerism / Solvent effect / Substituent effect / DFT caculation
Source:Chemistry Central Journal, 2012, 6