Redox-switchable 20π-, 19π-, and 18π-electron 5,10,15,20-tetraaryl-5,15-diazaporphyrinoid nickel(II) complexes

Takaharu Satoh, Mao Minoura, Haruyuki Nakano, Ko Furukawa, Yoshihiro Matano

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

The first examples of air-stable 20π-electron 5,10,15,20-tetraaryl-5,15-diaza-5,15-dihydroporphyrins, their 18π-electron dications, and the 19π-electron radical cation were prepared through metal-templated annulation of nickel(II) bis(5-arylamino-3-chloro-8-mesityldipyrrin) complexes followed by oxidation. The neutral 20π-electron derivatives are antiaromatic and the cationic 18π-electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins. N makes all the difference: Redox-switchable 20π-, 19π-, and 18π-electron 5,10,15,20-tetraaryl-5,15-diazaporphyrinoids are prepared through metal-templated annulation of NiII bis(dipyrrin) complexes followed by oxidation. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins.

Original languageEnglish
Pages (from-to)2235-2238
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number6
DOIs
Publication statusPublished - Feb 5 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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