Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 12, Issue 28, Pages 7804-7811Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b925561c
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Funding
- Spanish MICINN [MAT2007-65778-C02-01 and -02, CTQ2008-02820]
- Universidad Complutense of Madrid [GR58/08]
- Centro de Resonancia Magnetica of the Universidad Complutense de Madrid
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New BODIPY dyes with two 4-formylphenyl, 4-(2,2-dimethoxycarbonylvinyl) phenyl and 4-(2,2-dicyanovinyl) phenyl groups at the 3- and 5-positions have been successfully designed and synthesized via palladium-catalyzed coupling reaction or Knoevenagel-type condensations. Structural modi. cation of the BODIPY core via conjugation-extending residues significantly affects the spectroscopy and photophysical properties of the BODIPY fluorophore. These substituents cause the largest bathochromic shift in both absorption and emission spectra, which are shifted toward the red compared to its 4-phenylsubstituted analogue. Additionally, the fluorescence quantum yields and the Stokes shifts are also significantly higher than the corresponding phenyl-substituted dye. New BODIPY dyes have a high laser photostability, superior to that of commercial dyes with laser emission in the same spectral region, such as Perylene Red and Rhodamine 640. The substitution introduced in these derivatives allows to obtain tunable laser emission with a bandwidth of 0.15 cm(-1) and a tuning range of up to 50 nm. So with these three dyes it is possible to cover the spectral range 590-680 nm in a continuous way and with stable laser emission and small linewidth.
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