Meso-hydroxysubporphyrins: A cyclic trimeric assembly and a stable meso-Oxy radical

Daiki Shimizu, Juwon Oh, Ko Furukawa, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)


Treatment of meso-chlorosubporphyrin with potassium hydroxide in DMSO followed by aqueous work up and recrystallization gave a cyclic trimer consisting of meso-hydroxysubporphyrin units linked between the central boron atoms and meso-hydroxy groups. Solutions of this trimer are nonfluorescent, but become fluorescent when exposed to acid or base, since hydrolytic cleavage of the axial B-O bonds generates the meso-hydroxysubporphyrin monomer or its oxyanion. Ring cleavage of the trimer was also effected by reaction with phenylmagnesium bromide to produce meso-hydroxy-B-phenyl subporphyrin, which can be quantitatively oxidized with PbO2 to furnish a subporphyrin meso-oxy radical as a remarkably stable species as a result of spin delocalization over almost the entire molecule.

Original languageEnglish
Pages (from-to)6613-6617
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number22
Publication statusPublished - 2015 May 1

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry


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