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Red-Emitting Tetracoordinate Organoboron Chelates: Synthesis, Photophysical Properties, and Fluorescence Microscopy

 

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Opened Access Red-Emitting Tetracoordinate Organoboron Chelates: Synthesis, Photophysical Properties, and Fluorescence Microscopy
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Author: Pais, Vânia F.
Ramírez López, Pedro
Romero Arenas, Antonio
Collado, Daniel
Nájera, Francisco
Pérez Inestrosa, Ezequiel
Fernández Fernández, Rosario Fátima
Lassaletta, José M.
Ros, Abel
Pischel, Uwe
Department: Universidad de Sevilla. Departamento de Química Orgánica
Date: 2016
Published in: Journal of Organic Chemistry, 81 (20), 9605-9611.
Document type: Article
Abstract: 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), 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.
Cite: Pais, V.F., Ramírez López, P., Romero Arenas, A., Collado, D., Nájera, F., Pérez Inestrosa, E.,...,Pischel, U. (2016). Red-Emitting Tetracoordinate Organoboron Chelates: Synthesis, Photophysical Properties, and Fluorescence Microscopy. Journal of Organic Chemistry, 81 (20), 9605-9611.
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URI: https://hdl.handle.net/11441/76372

DOI: 10.1021/acs.joc.6b01569

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