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UV—vis spectroscopy of the coupling products of the palladium-catalyzed C—H arylation of the BODIPY core

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Abstract

The steady-state, UV—vis electronic absorption and fluorescence emission properties of a large set of 3-aryl and 3,5-diaryl substituted difluoroboron dipyrromethene dyes obtained via direct, palladiumcatalyzed C—H (het)arylation of the BODIPY core are reported. The spectra display the narrow absorption and fluorescence emission bands and the generally quite small Stokes shifts characteristic of classic difluoroboron dipyrrins. As a function of the solvent, the spectral maxima are located within a very narrow wavelength range and are slightly red-shifted with increasing solvent polarizability, which is shown to be the crucial parameter influencing the wavelength position of the maxima. The extended π-conjugation in the 3,5-diaryl products always leads to bathochromically shifted absorption and emission spectra compared to those of the 3-aryl analogues. The derivative with a 3-mesityl substituent has blue-shifted spectra in comparison to its 3-phenyl substituted analogue, reflecting the diminished π-conjugation in the former due to steric strain. The nature of the meso-aryl has only a small effect on the spectral positions but affects the fluorescence quantum yield Φ. The majority of the dyes have high Φ (>0.85), except the compounds with meso-phenyl and meso-(p-nitrophenyl) substituents. Quantumchemical calculations were performed to evaluate the differences in spectroscopic properties upon substitution of the BODIPY core and to compare them with the corresponding experimental results.

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Authors and Affiliations

  1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f—bus 02404, 3001, Leuven, Belgium

    Lina Wang, Bram Verbelen, Volker Leen, Wim Dehaen & Noël Boens

  2. Laboratory for Chemistry of Novel Materials, Université de Mons, Place du Parc 20, 7000, Mons, Belgium

    Claire Tonnelé, David Beljonne & Roberto Lazzaroni

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  1. Lina Wang
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  2. Bram Verbelen
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  3. Claire Tonnelé
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  8. Noël Boens
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Correspondence to Noël Boens.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c3pp25385f

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Wang, L., Verbelen, B., Tonnelé, C. et al. UV—vis spectroscopy of the coupling products of the palladium-catalyzed C—H arylation of the BODIPY core. Photochem Photobiol Sci 12, 835–847 (2013). https://doi.org/10.1039/c3pp25385f

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