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

Adel Alimmari; Dušan Mijin; Radovan Vukićević; Bojan Božić; Nataša Valentić; Vesna Vitnik; Zeljko Vitnik; Gordana Ušćumlić

doi:10.1186/1752-153X-6-71

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

Chem Cent J. 2012 Jul 23;6(1):71. doi: 10.1186/1752-153X-6-71.

Authors

Adel Alimmari¹, Dušan Mijin, Radovan Vukićević, Bojan Božić, Nataša Valentić, Vesna Vitnik, Zeljko Vitnik, Gordana Ušćumlić

Affiliation

¹ Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P,O, Box 3503, 11120, Belgrade, Serbia. kavur@tmf.bg.ac.rs.

Abstract

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.