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- Title
A Möbius Aromatic [28]Hexaphyrin Bearing a Diethylamine Group: A Rigid but Smooth Conjugation Circuit.
- Authors
Higashino, Tomohiro; Soya, Takanori; Osuka, Atsuhiro; Kim, Woojae; Kim, Dongho
- Abstract
The reaction of [26]hexaphyrin with triethylamine in the presence of BF3⋅OEt2 and O2 furnished a diastereomeric mixture of a diethylamine-bearing [28]hexaphyrin as a rare example of a Möbius aromatic metal-free expanded porphyrin. The Möbius aromaticity of these molecules is large, as indicated by their large diatropic ring currents, which are even preserved at 100 °C, owing to their internally multiply bridged robust structure with a smooth conjugation network. These molecules were reduced with NaBH4 to give an antiaromatic [28]hexaphyrin, and were oxidized with MnO2 to give aromatic [26]hexaphyrins, both through a Möbius-to-Hückel topology switch induced by a CN bond cleavage.
- Subjects
MOBIUS aromaticity; HEXAPHYRIN; TRIETHYLAMINE; PORPHYRINS; ELECTROSPRAY ionization mass spectrometry; HUCKEL molecular orbitals
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 18, p5456
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201500099