5,20-Diheterohexaphyrins: Metal-template-free synthesis and aromaticity switching

Masataka Umetani, Jinseok Kim, Takayuki Tanaka, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

As the first example of expanded heteroporphyrins with heteroatoms at meso-positions, 5,20-dithiahexaphyrins and 5,20-diazahexaphyrins were synthesized via nucleophilic substitution reactions of α,α′-dibromotripyrrin as the key step. While 5,20-dithiahexaphyrins are practically nonaromatic, 5,20-[28]diazahexaphyrins show weakly antiaromatic characters and can be cleanly converted into aromatic 5,20-[26]diazahexaphyrins upon oxidation with PbO2, demonstrating distinct aromaticity switching with maintenance of dumbbell-like conformations.

Original languageEnglish
Pages (from-to)10547-10550
Number of pages4
JournalChemical Communications
Volume55
Issue number71
DOIs
Publication statusPublished - 2019 Jan 1

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Conformations
Substitution reactions
Metals
Oxidation

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Umetani, Masataka ; Kim, Jinseok ; Tanaka, Takayuki ; Kim, Dongho ; Osuka, Atsuhiro. / 5,20-Diheterohexaphyrins : Metal-template-free synthesis and aromaticity switching. In: Chemical Communications. 2019 ; Vol. 55, No. 71. pp. 10547-10550.
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5,20-Diheterohexaphyrins : Metal-template-free synthesis and aromaticity switching. / Umetani, Masataka; Kim, Jinseok; Tanaka, Takayuki; Kim, Dongho; Osuka, Atsuhiro.

In: Chemical Communications, Vol. 55, No. 71, 01.01.2019, p. 10547-10550.

Research output: Contribution to journalArticle

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T1 - 5,20-Diheterohexaphyrins

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AU - Kim, Jinseok

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AU - Kim, Dongho

AU - Osuka, Atsuhiro

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