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

Abstract

Synthesis of a remarkably strained cyclopyrenylene trimer CP3 was achieved and it underwent the first metal-free direct oxygen insertion into the biaryl C–C σ-bond. A priori highly-strained CP3 exhibits the longest wavelength emission among whole pyrene-based fluorophores due to the intensive electronic interactions between pyrenes. The color of 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 a sulfur atom insertion into the biaryl σ-bond.

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Publication details

The article was received on 11 Apr 2019, accepted on 11 Jun 2019 and first published on 12 Jun 2019


Article type: Edge Article
DOI: 10.1039/C9SC01777A
Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    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, Accepted Manuscript , DOI: 10.1039/C9SC01777A

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