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

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 spe...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2014-03, Vol.126 (13), p.3495-3499
Main Authors: Ishida, Shin-ichiro, Higashino, Tomohiro, Mori, Shigeki, Mori, Hirotaka, Aratani, Naoki, Tanaka, Takayuki, Lim, Jong Min, Kim, Dongho, Osuka, Atsuhiro
Format: Article
Language:eng ; ger
Subjects:
Antiaromatizität
Chemistry
Formations
Hexaphyrin
Macrocyclic compounds
Möbius-Aromatizität
Protonation
Protonierung
Triangulare Strukturen
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Die Protonierung von [28]Hexaphyrinen(1.1.1.1.1.1) mit Trifluoressigsäure führt zu monoprotonierten Möbius‐aromatischen Strukturen, die Protonierung mit Methansulfonsäure ergibt dagegen diprotonierte triangulare antiaromatische Strukturen. Ein peripher hexaphenyliertes [28]Hexaphyrin wurde gezielt entworfen, um nach Diprotonierung eine triangulare antiaromatische Spezies zu bilden.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201400301