Red-Emitting Tetracoordinate Organoboron Chelates: Synthesis, Photophysical Properties, and Fluorescence Microscopy.
Seven tetracoordinate organoboron fluorophores with heterobiaryl N,O- or N,N-chelate ligands were prepared and photophysically characterized (in toluene). The electronic variation of the heteroaromatic moiety provided a means for the fine-tuning of the UV/vis absorption and emission spectra. In the most interesting cases, the spectra were red-shifted to maximum absorbance at wavelengths longer than 500 nm and emission maxima between 620 and 660 nm. The pronounced intramolecular charge-transfer character of the dyes yielded large Stokes shifts (3500-5100 cm-1), while maintaining appreciable fluorescence quantum yields of up to 0.2 for emission maxima longer than 600 nm. The lipophilic character of the dyes enabled their application as stains of vesicle substructures in confocal fluorescence microscopy imaging.
CIQSO, Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva , Campus de El Carmen s/n, 21071 Huelva, Spain.
Vânia F
VF
Pais
Institute for Chemical Research (CSIC-US) and Innovation-Center in Advanced Chemistry (ORFEO-CINQA) , C/Américo Vespucio 49, 41092 Seville, Spain.
Pedro
P
Ramírez-López
Institute for Chemical Research (CSIC-US) and Innovation-Center in Advanced Chemistry (ORFEO-CINQA) , C/Américo Vespucio 49, 41092 Seville, Spain.
Antonio
A
Romero-Arenas
Department of Organic Chemistry, University of Málaga, IBIMA , Campus Teatinos s/n, 29071 Málaga, Spain.|Andalusian Center for Nanomedicine and Biotechnology, BIONAND , Parque Tecnológico de Andalucía, 29590 Málaga, Spain.
Daniel
D
Collado
Department of Organic Chemistry, University of Málaga, IBIMA , Campus Teatinos s/n, 29071 Málaga, Spain.|Andalusian Center for Nanomedicine and Biotechnology, BIONAND , Parque Tecnológico de Andalucía, 29590 Málaga, Spain.
Francisco
F
Nájera
Department of Organic Chemistry, University of Málaga, IBIMA , Campus Teatinos s/n, 29071 Málaga, Spain.|Andalusian Center for Nanomedicine and Biotechnology, BIONAND , Parque Tecnológico de Andalucía, 29590 Málaga, Spain.
Ezequiel
E
Pérez-Inestrosa
Department of Organic Chemistry, University of Seville , and Innovation Center in Advanced Chemistry (ORFEO-CINQA), C/Prof. García González 1, 41012 Seville, Spain.
Rosario
R
Fernández
Institute for Chemical Research (CSIC-US) and Innovation-Center in Advanced Chemistry (ORFEO-CINQA) , C/Américo Vespucio 49, 41092 Seville, Spain.
José M
JM
Lassaletta
Institute for Chemical Research (CSIC-US) and Innovation-Center in Advanced Chemistry (ORFEO-CINQA) , C/Américo Vespucio 49, 41092 Seville, Spain.|Department of Organic Chemistry, University of Seville , and Innovation Center in Advanced Chemistry (ORFEO-CINQA), C/Prof. García González 1, 41012 Seville, Spain.
Abel
A
Ros
CIQSO, Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva , Campus de El Carmen s/n, 21071 Huelva, Spain.
Uwe
U
Pischel