Title: Ratiometric, fluorescent BODIPY dye with aza crown ether functionality: Synthesis, solvatochromism, and metal ion complex formation
Authors: Qin, Wenwu
Baruah, Mukulesh
Sliwa, Michel
Van der Auweraer, Mark
De Borggraeve, Wim
Beljonne, David
Van Averbeke, Bernard
Boens, Noël # ×
Issue Date: Jul-2008
Publisher: Amer chemical soc
Series Title: Journal of Physical Chemistry A vol:112 issue:27 pages:6104-6114
Abstract: A new pH and metal ion-responsive BODIPY-based fluorescent probe with an aza crown ether subunit has been synthesized via condensation of 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde with the appropriate 1,3,5,7-tetramethyl substituted boron dipyrromethene moiety. Steady-state and time-resolved fluorometries have been used to study the spectroscopic and photophysical characteristics of this probe in various solvents. The fluorescence properties of the dye are strongly solvent dependent: increasing the solvent polarity leads to lower fluorescence quantum yields and lifetimes, and the wavelength of maximum fluorescence emission shifts to the red. The Catalan solventscales are found to be the most suitable for describing the solvatochromic shifts of the fluorescence emission. Fluorescence decay profiles of the dye can be described by a single-exponential fit in nonprotic solvents, whereas two decay times are found in alcohols. Protonation as well as complex formation with several metal ions are investigated in acetonitrile as solvent via fluorometric titrations. The aza crown ether dye undergoes a reversible (de)protonation reaction (pKa = 0.09) and shows a similar to 50 nm blue shift in the excitation spectra and a 10-fold fluorescence increase upon protonation. The compound also forms 1:1 complexes with several metal ions (Li+, Na+, M2+, Ca2+ Ba2+ Zn2+), producing large blue shifts in the excitation spectra and significant cation-induced fluorescence amplifications.
ISSN: 1089-5639
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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