TY - JOUR
T1 - Diprotonated [28]hexaphyrins(1.1.1.1.1.1)
T2 - Triangular antiaromatic macrocycles
AU - Ishida, Shin Ichiro
AU - Higashino, Tomohiro
AU - Mori, Shigeki
AU - Mori, Hirotaka
AU - Aratani, Naoki
AU - Tanaka, Takayuki
AU - Lim, Jong Min
AU - Kim, Dongho
AU - Osuka, Atsuhiro
PY - 2014/3/24
Y1 - 2014/3/24
N2 - 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.
AB - 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.
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U2 - 10.1002/anie.201400301
DO - 10.1002/anie.201400301
M3 - Article
AN - SCOPUS:84896489194
SN - 1433-7851
VL - 53
SP - 3427
EP - 3431
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 13
ER -