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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

Title
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
Pak Y.L.Park S.J.Wu D.Cheon B.Kim H.M.Bouffard J.Yoon J.
Ewha Authors
윤주영Jean Bouffard
SCOPUS Author ID
윤주영scopus; Jean Bouffardscopus
Issue Date
2018
Journal Title
Angewandte Chemie - International Edition
ISSN
1433-7851JCR Link
Citation
Angewandte Chemie - International Edition vol. 57, no. 6, pp. 1567 - 1571
Keywords
boronfluorescence probesN-heterocyclic carbenesreactive oxygen speciestwo-photon microscopy
Publisher
Wiley-VCH Verlag
Indexed
SCI; SCIE; SCOPUS WOS scopus
Document Type
Article
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. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DOI
10.1002/anie.201711188
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자연과학대학 > 화학·나노과학전공 > Journal papers
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