New two-photon-absorbing probe with efficient superfluorescent properties

J Phys Chem B. 2010 Nov 11;114(44):14087-95. doi: 10.1021/jp107343k.

Abstract

The synthesis, linear photophysical, and photochemical parameters, two-photon absorption (2PA), and superfluorescence properties of 2,2'-(5,5'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(ethyne-2,1-diyl)bis(thiophene-5,2-diyl))dibenzo[d]thiazole (1) were investigated, suggesting its potential as an efficient fluorescent probe for bioimaging applications. The steady-state absorption, fluorescence, and excitation anisotropy spectra of 1 were measured in several organic solvents and aqueous media. Probe 1 exhibited high fluorescence quantum yield (~0.7-0.8) and photochemical stability (photobleaching quantum yield ~(3-7) × 10(-6)). The 2PA spectra were determined over a broad spectral range (640-920 nm) using a standard two-photon induced fluorescence method under femtosecond excitation. A well-defined two-photon allowed absorption band at 680-720 nm with corresponding 2PA cross sections δ(2PA) ≈ 800-900 GM was observed. The use of probe 1 in bioimaging was shown via one- and two-photon fluorescence imaging of HCT-116 cells. An amplification of the stimulated emission of 1 was demonstrated in organic solvents and thin polystyrene films, which potentially can be used for the development of new fluorescent labels with increased spectral brightness.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Absorption
  • Endosomes / metabolism
  • Fluorescence Polarization
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • HCT116 Cells
  • Humans
  • Lasers
  • Lysosomes / metabolism
  • Microscopy, Fluorescence
  • Photons*
  • Solvents / chemistry
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry*

Substances

  • 2,2'-(5,5'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(ethyne-2,1-diyl)bis(thiophene-5,2-diyl))dibenzo(d)thiazole
  • Fluorescent Dyes
  • Solvents
  • Thiazoles
  • Thiophenes