Azo-8-hydroxyquinoline dyes: The synthesis, characterizations and determination of tautomeric properties of some new phenyl- and heteroarylazo-8-hydroxyquinolines

Saylam A., SEFEROĞLU Z., Ertan N.

JOURNAL OF MOLECULAR LIQUIDS, vol.195, pp.267-276, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 195
  • Publication Date: 2014
  • Doi Number: 10.1016/j.molliq.2014.02.027
  • Journal Name: JOURNAL OF MOLECULAR LIQUIDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.267-276
  • Keywords: Phenylazo, Heteroarylazo, 8-Hydroxyquinoline, Azo-hydrazone, Absorption spectra, Solvent effect, CONTAINING HETEROCYCLIC ALDEHYDE, SPECTROSCOPIC PROPERTIES, METALLOCHROMIC MEROCYANINES, CRYSTAL-STRUCTURE, SN-119 MOSSBAUER, DISPERSE DYES, MONOAZO DYES, AZO DYES, COMPLEXES, STEREOCHEMISTRY
  • Gazi University Affiliated: Yes

Abstract

Two series of new heterocyclic and carbocyclic disperse azo dyes based on 8-hydroxyquinoline were prepared and characterized by FT-IR, H-1 NMR, mass spectroscopic techniques and elemental analysis. Their solvatochromic properties in different solvents were investigated and their absorption spectra were strongly solvent dependent The acid and base effects on this equilibrium were also examined. In addition, the colors of dyes were discussed with respect to the nature of the carbocyclic and heterocyclic rings and substituent therein. To determine the tautomeric forms of the prepared dyes in solid state, X-ray data for 5-(5-methylthiazol-2-yldiazenyl)-8-hydroxyquinoline were recorded. The X-ray results showed that the dye exists as an azo tautomer in the solid state. (C) 2014 Elsevier B.V. All rights reserved.