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Monofluorination and Trifluoromethylation of BODIPY Dyes for Prolonged Single‐Molecule Detection
Author(s) -
Huynh Anh Minh,
Menges Johannes,
Vester Michael,
Dier Tobias,
Huch Volker,
Volmer Dietrich A.,
Jung Gregor
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201500869
Subject(s) - trifluoromethylation , chemistry , photochemistry , bodipy , hypsochromic shift , fluorescence , reagent , nucleophile , fluorescence spectroscopy , intersystem crossing , electrophile , spectroscopy , molecule , trifluoromethyl , excited state , organic chemistry , alkyl , physics , singlet state , nuclear physics , catalysis , quantum mechanics
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.