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

3 Citations (Scopus)


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
Issue number71
Publication statusPublished - 2019 Jan 1

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

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