Monofluorination and Trifluoromethylation of BODIPY Dyes for Prolonged Single‐Molecule Detection
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| Authors: | Anh Minh Huynh Johannes Menges Michael Vester Tobias Dier Dr. Volker Huch Prof. Dr. Dietrich A. Volmer Prof. Dr. Gregor Jung |
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| Affiliation: | 1. Biophysical Chemistry, Saarland University, Campus Building B22, Saarbrücken, Germany;2. Institute of Bioanalytical Chemistry, Saarland University, Saarbrücken, Germany;3. Inorganic and General Chemistry, Saarland University, Saarbrücken, Germany |
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| Abstract: | Electrophilic monofluorination with Selectfluor and nucleophilic trifluoromethylation with the Ruppert–Prakesh reagent of dimethyl‐, tetramethyl‐ and pentamethyl‐substituted boron dipyrromethenes (BODIPY) are investigated. Monofluorinated dyes are synthesized with low yields (<30 %), however trifluoromethyl derivatives are obtained in moderate to high yields (≈40–90 %). All compounds are characterized by steady‐state and time‐resolved fluorescence spectroscopy, the photostability is investigated with fluorescence correlation spectroscopy (FCS) and total internal reflection fluorescence microscopy (TIRF). Monofluorination hardly affects the spectroscopic parameters of the unsubstituted parent compounds, but distinctly enhances the photostability, whereas trifluoromethylation leads to a hypsochromic shift by up to 17 nm in both absorption and emission, slightly enhanced intersystem crossing, and higher photostability. Further development of soft fluorination and trifluoromethylation methods is therefore highly desired. |
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| Keywords: | chromophores dyes/pigments fluorescence fluorescence spectroscopy photophysics |
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