Peripheral hexabromination, hexaphenylation, and hexaethynylation of meso-aryl-substituted subporphyrins

Eiji Tsurumaki, Yasuhide Inokuma, Shanmugam Easwaramoorthi, Jong Min Lim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Effective peripheral fabrication methods of meso-aryl-substituted subporphyrins were explored for the first time. Hexabrominated subporphyrins 2 were prepared quantitatively from the bromination of subporphyrins 1 with bromine. Hexaphenylated subporphyrins 3 and hexaethynylated subporphyrins 4 and 5 were synthesized by Suzuki-Miyaura coupling and Stille coupling, respectively, in good yields. X-ray crystal structures of 2b, 3b, 4b, and 5 a revealed preservation of the bowl-shaped bent structures with bowl depths similar to that of 1. Hexaethynylated subporphyrins exhibit large two-photon-absorption cross-sections due to effective derealization of the conjugated network to the ethynyl substituents.

Original languageEnglish
Pages (from-to)237-247
Number of pages11
JournalChemistry - A European Journal
Volume15
Issue number1
DOIs
Publication statusPublished - 2009 Jan 27

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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