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N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues
Author(s) -
Pak Yen Leng,
Park Sang Jun,
Wu Di,
Cheon BoHyun,
Kim Hwan Myung,
Bouffard Jean,
Yoon Juyoung
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711188
Subject(s) - hypochlorous acid , boranes , chemistry , carbene , electrophile , nucleophile , reactive oxygen species , photochemistry , selectivity , peroxynitrite , reactive intermediate , organic chemistry , catalysis , boron , superoxide , biochemistry , enzyme
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.