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Aromatic and Antiaromatic Cyclophane‐type Hexaphyrin Dimers
Author(s) -
Nakai Akito,
Yoneda Tomoki,
Ishida Shinichiro,
Kato Kenichi,
Osuka Atsuhiro
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801751
Subject(s) - antiaromaticity , cyclophane , chemistry , aromaticity , dimer , intermolecular force , photochemistry , crystallography , molecule , organic chemistry , crystal structure
A peripherally strapped [28]hexaphyrin takes a rectangular conformation and exhibits antiaromatic character. A cyclophane‐type dimer consisting of such [28]hexaphyrins was synthesized from hexakis(pentafluorophenyl) [26]hexaphyrin via S N Ar reaction with allyl alcohol, one‐pot intra‐ and intermolecular olefin metathesis under improved Hoveyda–Grubbs catalysis, and final reduction with NaBH 4 . The cyclophane‐type structures of [26]‐ and [28]hexaphyrin dimers have been revealed by X‐ray analysis. Studies on the structural, optical, and electronic properties have led to a conclusion that there is no favorable electronic interaction between the two [28]hexaphyrin segments and thus no indication of 3D aromaticity.