2-phenoxathiinyl-5-phenyloxazole and 5-phenoxathiinyl-2-phenyloxazole derivatives: experimental and theoretical study of emission properties

Spectrochim Acta A Mol Biomol Spectrosc. 2007 Apr;66(4-5):1165-70. doi: 10.1016/j.saa.2006.06.001. Epub 2006 Jun 13.

Abstract

The absorption and emission spectra in cyclohexane and methanol of the title phenoxathiinyl-phenyloxazole derivatives are presented and discussed. Comparing to the unsubstituted diphenyloxazole (PPO), the experimental results show a bathochromic shift of the emission band, a significant dependence of the maximum on the solvent polarity and a drastic decrease of the fluorescence quantum yield. Semiempirical MO calculations (AM1) in both the ground and excited states support the experimental findings. A charge transfer from the phenoxathiin fragment to the oxazole ring is predicted in the excited state explaining the solvatochromism of the compounds. The values for the singlet-triplet gap, 3500-5000 cm-1 point to an enhanced probability of intersystem crossing (ISC) non-radiative deactivation processes, in agreement with the low fluorescence quantum yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Cyclohexanes / chemistry
  • Methanol / chemistry
  • Models, Chemical*
  • Oxazoles / chemistry*
  • Spectrometry, Fluorescence
  • Static Electricity

Substances

  • 5-phenoxathiinyl-2-phenyloxazole
  • Acetonitriles
  • Cyclohexanes
  • Oxazoles
  • Cyclohexane
  • Methanol
  • acetonitrile