New Two-Photon-Absorbing Probe With Efficient Superfluorescent Properties

The synthesis, linear photophysical, and photochemical parameters, two-photon absorption (2PA), and superfluorescence properties of 2,2\u27-(5,5\u27-(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 δ2PA ≈ 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. © 2010 American Chemical Society