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'-(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.
Belfield
Kevin D
KD
Department of Chemistry, University of Central Florida, P.O. Box 162366, Orlando, Florida 32816-2366, USA.
Andrade
Carolina D
CD
Yanez
Ciceron O
CO
Bondar
Mykhailo V
MV
Hernandez
Florencio E
FE
Przhonska
Olga V
OV
D000042:Absorption; D011992:Endosomes / Q000378:metabolism; D005454:Fluorescence Polarization; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D045325:HCT116 Cells; D006801:Humans; D007834:Lasers; D008247:Lysosomes / Q000378:metabolism; D008856:Microscopy, Fluorescence; D017785:Photons; D012997:Solvents / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry*
C555858:2,2'-(5,5'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(ethyne-2,1-diyl)bis(thiophene-5,2-diyl))dibenzo(d)thiazole; D005456:Fluorescent Dyes; D012997:Solvents; D013844:Thiazoles; D013876:Thiophenes