Title: BODIPY-based hydroxyaryl derivatives as fluorescent pH probes
Authors: Baruah, Mukulesh ×
Qin, WW
Basaric, N
De Borggraeve, Wim
Boens, Noël #
Issue Date: May-2005
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:70 issue:10 pages:4152-4157
Abstract: Seven new 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with phenolic or naphtholic subunits on position 8 and with substituents having different electron driving forces on positions 3 and 5 were synthesized. Their absorption and steady-state fluorescence properties were investigated as a function of solvent. The novel compounds, with the exception of 4,4-difluoro-8-(4-hydroxyphenyl)-3,5-bis-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene, are characterized by absorption maxima in the range 493-515 nm and small (400-600 cm(-1)) Stokes shifts. The exceptional dye has absorption maxima in the 570-580 nm region and fluorescence emission maxima around 610-620 nm, depending on the solvent. In aqueous solution, the dyes show a large fluorescent enhancement upon increasing the acidity of the solution. They can be used in aqueous solution as fluorescent pH probes excitable with visible light, with pK(a) values ranging from 7.5 to 9.3, depending on the substitution pattern on positions 3, 5, and 8.
ISSN: 0022-3263
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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