Imidazole-based excited-state intramolecular proton-transfer (ESIPT) materials: observation of thermally activated delayed fluorescence (TDF)

J Phys Chem A. 2007 Oct 4;111(39):9649-53. doi: 10.1021/jp072212p. Epub 2007 Aug 31.

Abstract

We report the first observation of thermally activated delayed fluorescence (TDF) from an excited-state intramolecular proton-transfer (ESIPT) molecule, a hydroxyl-substituted tetraphenyl imidazole derivative (HPI-Ac), in degassed solutions as well as in low-temperature organic matrixes. In the absence of oxygen, the blue emission of an identical spectral feature was observed in the nanosecond ( approximately 4.4 ns) and microsecond ( approximately 25 micros) time domains, and the fluorescence intensity increased with temperature. From the temperature dependence of the time-resolved spectra of HPI-Ac, the energy gap between the first-excited singlet state and the lowest triplet state was determined to be 7.6 +/- 0.3 kJ/mol (630 +/- 25 cm-1), and the limiting rate constant of intrinsic reverse intersystem crossing was estimated to be 1.3 (+/-0.5) x 107 s-1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry, Physical / methods
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Hot Temperature
  • Imidazoles / chemistry*
  • Imidazoles / pharmacology
  • Kinetics
  • Models, Chemical
  • Protons
  • Spectrometry, Fluorescence / methods*
  • Spectrophotometry / methods
  • Temperature
  • Thermodynamics
  • Time Factors

Substances

  • Enzyme Inhibitors
  • Imidazoles
  • Protons
  • imidazole