Photophysical Characterization of New 3-Amino and 3-Acetamido BODIPY Dyes with Solvent Sensitive Properties |
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Authors: | J Bañuelos F López Arbeloa T Arbeloa S Salleres J L Vilas F Amat-Guerri M Liras I López Arbeloa |
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Institution: | (1) Departamento de Química Física, Universidad del País Vasco-EHU, Apartado 644, 48080 Bilbao, Spain;(2) Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain;(3) Universidad Miguel Hernández (UMH), Avda. Ferrocarril s/n, Edificio Torrevaillo, Elche, 03202, Alicante, Spain |
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Abstract: | 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 π-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 × 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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Keywords: | Photophysics BODIPY dyes Substituent effect Solvent effect Fluorescent acid probe |
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