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We report a simple and efficient strategy to enhance the fluorescence of biocompatible biindole diketonates (bdks) in the visible spectrum through difluoroboronation (BF₂bdks complexes). Emission spectroscopy testifies an increase in the fluorescence quantum yields from a few percent to as much as >0.7. This massive increment is essentially independent of substitutions at the indole (-H, -Cl, and -OCH₃) and corresponds to a significant stabilization of the excited state with respect to non-radiative decay mechanisms: the non-radiative decay rates are reduced by as much as an order of magnitude, from 10⁹ s⁻¹ to 10⁸ s⁻¹, upon difluoroboronation. The stabilization of the excited state is large enough to enable sizeable ¹O₂ photosensitized production. Different time-dependent (TD) density functional theory (DFT) methods were assessed in their ability to model the electronic properties of the compounds, with TD-B3LYP-D3 providing the most accurate excitation energies. The calculations associate the first active optical transition in both the bdks and BF₂bdks electronic spectra to the <i>S</i>₀ → <i>S</i>₁ transition, corresponding to a shift in the electronic density from the indoles to the oxygens or the O-BF₂-O unit, respectively.