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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
Authors:Yen Leng Pak  Sang Jun Park  Dr. Di Wu  BoHyun Cheon  Prof. Hwan Myung Kim  Prof. Jean Bouffard  Prof. Juyoung Yoon
Affiliation:1. Department of Chemistry and Nano Science (BK 21 Plus), Ewha Womans University, Seoul, Korea;2. Department of Chemistry and Energy Systems Research, Ajou University, Suwon, Korea
Abstract: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.
Keywords:boron  fluorescence probes  N-heterocyclic carbenes  reactive oxygen species  two-photon microscopy
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