Triply linked corrole dimers

Shota Ooi, Takayuki Tanaka, Kyu Hyung Park, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

The oxidation of 10-10′ singly linked corrole dimers with DDQ at low concentration in CHCl3 afforded meso-meso, β-β, β-β triply linked 2H-corrole dimers (with two inner NH groups in each corrole unit), which exhibited characteristic 1H NMR and absorption spectra attributable to their nonaromatic electronic networks. These 2H-corrole dimers were reduced with NaBH4 to aromatic 3H-corrole dimers, which were unstable and easily oxidized back to the 2H-corrole dimers upon exposure to air. Bis(zinc(II)) complexes of the 2H-corrole dimers were synthesized and characterized as rare examples of nonaromatic zinc(II) corrole complexes. The oxidation of singly 10,10′-linked corrole dimers with DDQ at low concentration in CHCl3 afforded stable triply linked 2H-corrole dimers. These dimers were shown to be non-aromatic on the basis of 1H NMR spectroscopy and DFT calculations, and were reduced with NaBH4 to aromatic 3H-corrole dimers, which were unstable and easily reoxidized to the 2H-corrole dimers upon exposure to air.

Original languageEnglish
Pages (from-to)6535-6539
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number22
DOIs
Publication statusPublished - 2016 May 23

Bibliographical note

Funding Information:
The work at Kyoto was supported by JSPS KAKENHI Grants (25220802 and 25620031). The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183).

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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