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Issue 28, 2019
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A remarkably strained cyclopyrenylene trimer that undergoes metal-free direct oxygen insertion into the biaryl C–C σ-bond

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Abstract

A remarkably strained cyclopyrenylene trimer CP3 was synthesized and it underwent the first biaryl C–C σ-bond cleavage by direct oxygen insertion without the aid of any metal agents. A priori highly strained CP3 exhibits the longest wavelength emission among all pyrene-based fluorophores due to the intensive electronic interactions between pyrenes. The color of the emission drastically changes from orange to light blue upon oxidation. Theoretical studies revealed that the release of ring strain reasonably drives the reaction between two CP3 molecules and O2. This strain-induced transformation could be also applied for sulfur atom insertion into a biaryl σ-bond.

Graphical abstract: A remarkably strained cyclopyrenylene trimer that undergoes metal-free direct oxygen insertion into the biaryl C–C σ-bond

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Article information


Submitted
11 Apr 2019
Accepted
11 Jun 2019
First published
12 Jun 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 6785-6790
Article type
Edge Article

A remarkably strained cyclopyrenylene trimer that undergoes metal-free direct oxygen insertion into the biaryl C–C σ-bond

R. Kurosaki, H. Hayashi, M. Suzuki, J. Jiang, M. Hatanaka, N. Aratani and H. Yamada, Chem. Sci., 2019, 10, 6785
DOI: 10.1039/C9SC01777A

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