N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues |
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Authors: | Yen Leng Pak Sang Jun Park Dr. Di Wu BoHyun Cheon Prof. Hwan Myung Kim Prof. Jean Bouffard Prof. Juyoung Yoon |
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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 |
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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. |
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Keywords: | boron fluorescence probes N-heterocyclic carbenes reactive oxygen species two-photon microscopy |
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