Diprotonated [28]hexaphyrins(1.1.1.1.1.1): Triangular antiaromatic macrocycles

Shin Ichiro Ishida, Tomohiro Higashino, Shigeki Mori, Hirotaka Mori, Naoki Aratani, Takayuki Tanaka, Jong Min Lim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Protonation of meso-aryl [28]hexaphyrins(1.1.1.1.1.1) triggered conformational changes. Whereas protonation with trifluoroacetic acid led to the formation of monoprotonated Möbius aromatic species, protonation with methanesulfonic acid led to the formation of diprotonated triangular antiaromatic species. A peripherally hexaphenylated [28]hexaphyrin was rationally designed and prepared to undergo diprotonation to favorably afford a triangular-shaped antiaromatic species. Protonation of [28]hexaphyrins(1.1.1.1. 1.1) triggers conformational changes. Whereas protonation with trifluoroacetic acid leads to the formation of monoprotonated Möbius aromatic species, protonation with methanesulfonic acid leads to the formation of diprotonated triangular antiaromatic species. A peripherally hexaphenylated [28]hexaphyrin was rationally designed to undergo diprotonation to afford a triangular-shaped antiaromatic species.

Original languageEnglish
Pages (from-to)3427-3431
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number13
DOIs
Publication statusPublished - 2014 Mar 24

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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    Ishida, S. I., Higashino, T., Mori, S., Mori, H., Aratani, N., Tanaka, T., Lim, J. M., Kim, D., & Osuka, A. (2014). Diprotonated [28]hexaphyrins(1.1.1.1.1.1): Triangular antiaromatic macrocycles. Angewandte Chemie - International Edition, 53(13), 3427-3431. https://doi.org/10.1002/anie.201400301