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Yutaro Koyama, Dr. Satoru Hiroto and Prof. Dr. Hiroshi Shinokubo Synthesis of Highly Distorted π-Extended [2.2]Metacyclophanes by Intermolecular Double Oxidative Coupling Angewandte Chemie International Edition 52

Version of Record online: 22 APR 2013 | DOI: 10.1002/anie.201301180

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A strained relationship: Oxidation of dihydroxy-substituted acenes provides face-to-face [2.2]metacyclophane-like dimers (see scheme; O red, Si of iPr3Si 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.

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