Phenylazoindole dyes - Part I: The syntheses, characterizations, crystal structures, quantum chemical calculations and antimicrobial properties

SEFEROĞLU Z., Yalcin E., Babur B., SEFEROĞLU N., HÖKELEK T., Yilmaz E., ...More

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol.113, pp.314-324, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 113
  • Publication Date: 2013
  • Doi Number: 10.1016/j.saa.2013.04.081
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.314-324
  • Keywords: Phenylazoindole dye, Azo-hydrazone tautomer, Crystal structure, DFT calculations, Antimicrobial activity, MONOAZO DISPERSE DYE, AZO DYES, DERIVATIVES, ABSORPTION, DECOLORISATION, INDOLE
  • Gazi University Affiliated: Yes


In this study, the synthesis of four new phenylazo indole dyes (dye 1-4) were carried out by diazotization of 4-aminoacetophenone and coupling with various 2- and 1,2-disubstituted indole derivatives. The dyes were characterized by UV-vis, FT-IR, H-1 NMR, HRMS and X-ray single crystal diffraction methods. Azo-hydrazone tautomeric bahavior of the dyes in different solvents (DMSO, methanol, acetic acid and chloroform) was investigated by using H-1 NMR and UV-vis results. The experimental results were compared with the corresponding calculated values. The results of experimental data and theoretical calculations showed that the azo tautomer is more stable than hydrazone tautomer. In addition to this, the antimicrobial activity of the dyes was also evaluated. Published by Elsevier B.V.