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Conformational Fixation of a Rectangular Antiaromatic [28]Hexaphyrin Using Rationally Installed Peripheral Straps
Author(s) -
Yoneda Tomoki,
Kim Taeyeon,
Soya Takanori,
Neya Saburo,
Oh Juwon,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600262
Subject(s) - antiaromaticity , intramolecular force , chemistry , photochemistry , aromaticity , stereochemistry , organic chemistry , molecule
A rectangular [28]hexaphyrin bearing outer straps at the long side has been synthesized by S N Ar reaction of [26]hexaphyrin with allyl alcohol, intramolecular olefin metathesis by using Hoveyda–Grubbs second‐generation catalyst, and reduction with NaBH 4 . The peripheral straps enforce a rectangular conformation for the [28]hexaphyrin, which shows Hückel antiaromatic character, as confirmed by its planar X‐ray structure, a strong paratropic ring current, characteristic UV/Vis/NIR absorption features, small electrochemical HOMO–LUMO gap, and very fast S 1 decay.