Synthesis and structure of a novel hetarylazoindole dye studied by X-ray diffraction, FT-IR, FT-Raman, UV-vis, NMR spectra and DFT calculations


AKTAN E. , Babur B., SEFEROĞLU Z. , HÖKELEK T., Sahin E.

JOURNAL OF MOLECULAR STRUCTURE, vol.1002, pp.113-120, 2011 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1002
  • Publication Date: 2011
  • Doi Number: 10.1016/j.molstruc.2011.07.007
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Page Numbers: pp.113-120
  • Keywords: Hetarylazoindole dye, Crystal structure, DFT, TD-DFT, SQM, DENSITY-FUNCTIONAL THEORY, DISPERSE DYES, AB-INITIO, ABSORPTION-SPECTRA, CRYSTAL-STRUCTURE, SPECTROSCOPIC PROPERTIES, MOLECULAR GEOMETRIES, EMPIRICAL CORRECTION, AZO DYES, TAUTOMERISM

Abstract

A novel hetarylazoindole dye, 1,2-dimethyl-3-(pyridin-3-yldiazenyl)-1H-indole (DMPI) was synthesized by coupling 1,2-dimethylindole with diazotized 3-aminopyridine. The dye was characterized by FT-IR. FT-Raman, UV vis, H-1 NMR, C-13 NMR and X-ray diffraction techniques. The structure of the dye was determined by X-ray single crystal diffraction method. The molecular geometry, Gauge including atomic orbital (CIAO) H-1- and C-13 NMR chemical shift values and vibrational frequencies of DMPI molecule in the ground state were calculated by using the density functional theory (DFT). The theoretical electronic absorption spectra were calculated using time-dependent density functional theory (TD-DFT). The total energy distributions (TED) of the vibrational modes were calculated by using scaled quantum mechanical (SQM) analysis. (C) 2011 Elsevier B.V. All rights reserved.