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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.