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BODIPY Fluorophore Toolkit for Probing Chemical Reactivity and for Tagging Reactive Functional Groups
Author(s) -
Hensle Eva M.,
Esfandiari N. Melody,
Lim SungGon,
Blum Suzanne A.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400052
Subject(s) - bodipy , fluorophore , chemistry , förster resonance energy transfer , fluorescence , photochemistry , reagent , combinatorial chemistry , chemical reaction , click chemistry , chemical transformation , nanotechnology , organic chemistry , materials science , physics , quantum mechanics
The photophysical and synthetic studies of new tether‐functionalized boron dipyrromethene (BODIPY) fluorophores as probes for chemical reactions are described. These compounds differ from typically reported probes in that they provide a way to tag and indicate chemical reactions without chemical transformation of the BODIPY core itself; instead the dyes are spectators. The introduction and modification of the tether has expanded the available chemistry and yet these new BODIPY derivatives have similar photophysical properties to their parent substrates. As a result of the chemistry enabled by these probes, a single step of a multistep metal‐catalyzed reaction was revealed by a change in the fluorescence resonance energy transfer (FRET) signal. The fundamental knowledge of quantum yield, FRET efficiencies, and reagent compatibility is critical to enabling the broader application of fluorescent probes to study chemical reaction mechanisms by cutting‐edge microscopy techniques.