Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

• Main Authors: Alimmari Adel, Mijin Dušan, Vukićević Radovan, Božić Bojan, Valentić Nataša, Vitnik Vesna, Vitnik Željko, Ušćumlić Gordana
• Format: Article
• Language: English
• Published: BMC 2012-07-01
• Series: Chemistry Central Journal
• Subjects: Arylazo pyridone dyes; Tautomerism; Solvent effect; Substituent effect; DFT caculation
• Online Access: http://journal.chemistrycentral.com/content/6/1/71
• ISSN: 1752-153X

<p>Abstract</p> <p>Background</p> <p>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.</p> <p>Results</p> <p>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.</p> <p>Conclusions</p> <p>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.</p>