Efficient fluorophores based on pyridyl-enolato and enamido difluoroboron complexes: Simple alternatives to boron-dipyrromethene (bodipy) dyes

Difluoroboron complexes of unsymmetric [N,O] and [N,N] chelate ligands based on pyridyl or quinolyl enolates or enamides can be synthesized easily. They are efficient fluorophores with potential applications as biolabels, due to their convenient functionalization by simple condensation reactions wit...

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Bibliographic Details
Published in:Inorganica Chimica Acta 2013-08, Vol.405, p.116-120
Main Authors: Graser, Markus, Kopacka, Holger, Wurst, Klaus, Ruetz, Markus, Kreutz, Christoph R., Müller, Thomas, Hirtenlehner, Christa, Monkowius, Uwe, Knör, Günther, Bildstein, Benno
Format: Article
Language:English
Subjects:
Boron complex
Fluorescence
N ligand
N,O ligand
X-ray structure
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Summary:Difluoroboron complexes of unsymmetric [N,O] and [N,N] chelate ligands based on pyridyl or quinolyl enolates or enamides can be synthesized easily. They are efficient fluorophores with potential applications as biolabels, due to their convenient functionalization by simple condensation reactions with primary amines. •Simple, desymmetrized fluorophores.•BODIPY-like photophysical properties.•Potentially useful biolabel precursors. Simple [N,O] and [N,N]β-pyridyl or quinolyl enolato/enamido difluoroboron complexes are easily accessible and highly luminescent with good photophysical properties, comparable to BODIPY benchmark dyes. Complete characterization by multinuclear NMR and by single crystal structure analysis as well as pertinent photophysical data are reported.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2013.05.034