Strained Cyclopyrenylene Trimer Has Unusual Reactivity

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  • Published: 16 June 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Science/Royal Society of Chemistry
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: Strained Cyclopyrenylene Trimer Has Unusual Reactivity

Cycloparaphenylenes (CPPs) often have unique properties that are caused by their curved π-conjugated systems. They can, for example, be used as fluorophores. Cyclic molecules, in general, can have interesting reactivities caused by ring strain, whose release can be a driving force for reactions.

Naoki Aratani, Hiroko Yamada, Nara Institute of Science and Technology (NAIST), Japan, and colleagues have synthesized a strained, trimeric cycloparaphenylene (pictured, R = C3H7). The compound was prepared via a nickel-catalyzed coupling of 1,8-dibromo-4,5-dipropoxypyrenes. The trimer was separated from other products by chromatography.

The team found that the strained trimer has an unusual reactivity: Under ambient conditions and room light in air, the compound is converted into a biaryl ether at one of the Caryl–Caryl bonds. According to the researchers, this is the first metal-free direct oxygen atom insertion into a biaryl C–C σ-bond at ambient conditions. The color of emission changes from orange to light blue during this oxidation reaction. The reaction with O2 is driven by the release of ring strain.


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