Phenylazoindole dyes 3: Determination of azo-hydrazone tautomers of new phenylazoindole dyes in solution and solid state

Babur B., SEFEROĞLU N., AKTAN E., HÖKELEK T., ŞAHİN E., SEFEROĞLU Z.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1081, ss.175-181, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1081
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.moistruc.2014.09.082
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.175-181
  • Anahtar Kelimeler: Azo dyes, Phenylazoindole dyes, Azo-hydrazone tautomers, Crystal structures, DFT calculations, SPECTROSCOPIC PROPERTIES, AZOBENZENE, ABSORPTION, N-15-NMR, SPECTRA, ACID, NMR
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new two series of phenylazo indole dyes was synthesized and the structures of the dyes were confirmed by UV vis, FT-IR, HRMS and H-1/C-13 NMR spectroscopic techniques. Five of these dyes (I, I', II', HI and were also characterized in solid state by using single crystal X-ray diffraction studies besides other spectroscopic techniques. The geometries of the azo and hydrazone tautomeric forms of the dyes were optimized by using Density Functional Theory (DFT). In addition, the effects of the donor and acceptor groups on the azo and hydrazone forms of the dyes were evaluated experimentally and theoretically. The results indicate that the phenylazoindole dyes derived from 2-phenyl indole as coupling component exist as azo form in solution, gas phase and solid state. (C) 2014 Elsevier B.V. All rights reserved.