Triply linked corrole dimers

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

Research output: Contribution to journalArticle

27 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

Fingerprint

Dimers
Zinc
corrole
Oxidation
Air
Discrete Fourier transforms
Nuclear magnetic resonance spectroscopy
Absorption spectra
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Ooi, Shota ; Tanaka, Takayuki ; Park, Kyu Hyung ; Kim, Dongho ; Osuka, Atsuhiro. / Triply linked corrole dimers. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 22. pp. 6535-6539.
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Ooi, S, Tanaka, T, Park, KH, Kim, D & Osuka, A 2016, 'Triply linked corrole dimers', Angewandte Chemie - International Edition, vol. 55, no. 22, pp. 6535-6539. https://doi.org/10.1002/anie.201601864

Triply linked corrole dimers. / Ooi, Shota; Tanaka, Takayuki; Park, Kyu Hyung; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 55, No. 22, 23.05.2016, p. 6535-6539.

Research output: Contribution to journalArticle

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