Diprotonated [28]Hexaphyrins(1.1.1.1.1.1): Triangular Antiaromatic Macrocycles | Zendy

Ishida Shinichiro | Zendy; Higashino Tomohiro | Zendy; Mori Shigeki | Zendy; Mori Hirotaka | Zendy; Aratani Naoki | Zendy; Tanaka Takayuki | Zendy; Lim Jong Min | Zendy; Kim Dongho | Zendy; Osuka Atsuhiro | Zendy

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Diprotonated [28]Hexaphyrins(1.1.1.1.1.1): Triangular Antiaromatic Macrocycles

Author(s) -

Ishida Shinichiro,

Higashino Tomohiro,

Mori Shigeki,

Mori Hirotaka,

Aratani Naoki,

Tanaka Takayuki,

Lim Jong Min,

Kim Dongho,

Osuka Atsuhiro

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201400301

Subject(s) - antiaromaticity , protonation , trifluoroacetic acid , methanesulfonic acid , chemistry , aromaticity , stereochemistry , organic chemistry , molecule , ion

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.

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