Excited-state intramolecular charge transfer in 9-aminoacridine derivative

J Phys Chem A. 2005 Jul 14;109(27):5978-83. doi: 10.1021/jp044704x.

Abstract

A new fluorochromic dye was obtained from the reaction of 9-aminoacridine with ethyl-2-cyano-3-ethoxyacrylate. It displays complex fluorescence that is ascribed to normal emission from the acridine chromophore in addition to excited-state intramolecular charge transfer (ESICT) formed upon light excitation. The analysis of the fluorescence decays in different solvents reveals two short-lived components in the range of 80-450 ps and 0.7-3.2 ns, ascribed to the formation and decay of the intramolecular charge transfer (ICT) state, in addition to a third component of about 9.0 ns, which is related to the normal emission from the acridine singlet excited state, probably in an enol-imine tautomeric form. The ICT emission is readily quenched by water addition to polar solvents, and this effect is ascribed to changes in the keto-amine/enol-imine equilibrium of this fluorochromic dye.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminacrine / chemistry*
  • Chromatography, Liquid
  • Energy Transfer*
  • Fluorescence*
  • Fluorescent Dyes / chemistry*
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Photochemistry*
  • Solvents / chemistry*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Fluorescent Dyes
  • Solvents
  • Aminacrine