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 journalArticle

37 Citations (Scopus)

Abstract

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
Volume54
Issue number22
DOIs
Publication statusPublished - 2015 May 1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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