Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 6, Pages 1567-1571Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711188
Keywords
boron; fluorescence probes; N-heterocyclic carbenes; reactive oxygen species; two-photon microscopy
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Funding
- National Research Foundation of Korea [2012R1A3A2048814, 2016R1E1A1A02920873, 2015R1D1A1A01059383]
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N-Heterocyclic carbene (NHC) boranes undergo oxidative hydrolysis to give imidazolium salts with excellent kinetic selectivity for HOCl over other reactive oxygen species (ROS), including peroxides and peroxynitrite. Selectivity for HOCl results from the electrophilic oxidation mechanism of NHC boranes, which stands in contrast to the nucleophilic oxidation mechanism of arylboronic acids with ROS. The change in polarity that accompanies the conversion of NHC boranes to imidazolium salts can control the formation of emissive excimers, forming the basis for the design of the first fluorescence probe for ROS based on the oxidation of B-H bonds. Two-photon microscope (TPM) ratiometric imaging of HOCl in living cells and tissues is demonstrated.
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