Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones | Zendy

Adel Alimmari | Zendy; Аleksandar Marinković | Zendy; Dušan Mijin | Zendy; Nataša Valentić | Zendy; Nina Todorović | Zendy; Gordana Uščumlić | Zendy

Open Access

Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones

Author(s) -

Adel Alimmari,

Аleksandar Marinković,

Dušan Mijin,

Nataša Valentić,

Nina Todorović,

Gordana Uščumlić

Publication year - 2010

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc091009074a

Subject(s) - solvatochromism , chemistry , tautomer , solvation , polarizability , solvent , hydrogen bond , photochemistry , solvent effects , computational chemistry , organic chemistry , molecule

A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1 H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipola- rity/polarizability and solvent/solute hydrogen bonding interactions were ana- lyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.

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