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Synthesis of Highly Distorted π‐Extended [2.2]Metacyclophanes by Intermolecular Double Oxidative Coupling
Author(s) -
Koyama Yutaro,
Hiroto Satoru,
Shinokubo Hiroshi
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301180
Subject(s) - steric effects , intermolecular force , chemistry , electrochemistry , coupling (piping) , scheme (mathematics) , homo/lumo , face (sociological concept) , computer science , crystallography , stereochemistry , materials science , molecule , sociology , organic chemistry , mathematics , mathematical analysis , social science , electrode , metallurgy
A strained relationship : Oxidation of dihydroxy‐substituted acenes provides face‐to‐face [2.2]metacyclophane‐like dimers (see scheme; O red, Si of i Pr 3 Si groups blue). The products exhibited highly distorted structures caused by steric repulsion. UV/Vis and electrochemical analysis revealed that the HOMO–LUMO gap was decreased upon dimerization.