Journal
JOURNAL OF FLUORESCENCE
Volume 18, Issue 5, Pages 899-907Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s10895-008-0320-7
Keywords
photophysics; BODIPY dyes; substituent effect; solvent effect; fluorescent acid probe
Funding
- Spanish Ministerio de Educacion y Ciencia [MAT2004-04643-C03-01, MAT2004-04643-C03-02]
- Spanish MEC
- European Social Fund
- UPV/EHU
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The structural, electronic and photophysical properties of three new asymmetric, highly fluorescent difluoroborondipyrromethene (BODIPY) dyes, bearing an amino or an acetamido group at position 3 of the chromophoric core, have been studied in different apolar, polar and polar/protic solvents. The presence of the 3-amido group extents the delocalization of the pi-system, leading to bathochromic shifts in the absorption and fluorescence bands, as predicted by quantum mechanic calculations. The 3-amino dye shows photophysical properties highly dependent on the solvent polarity and acidity, and is characterized by a hypsochromic shift of its absorption band, with regard to the corresponding acetylated dye, as well as a low fluorescence quantum yield in acid media with proton concentration lower than 4 x 10(-4) M. In media with higher proton concentration, the BF2 bridge group of the 3-amino dye is removed, yielding the corresponding non-fluorescent dipyrromethene precursor. These results suggest that the 3-amino dye could be used as a fluorescence probe for the study of the acidity of different environments.
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