Bowled Over by Single Isomer of Bisumanenyl

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 22 August 2013
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Bowled Over by Single Isomer of Bisumanenyl

Bowl-shaped π-conjugated compounds (π bowls) are an important class of non-planar carbon-based materials, alongside fullerenes and carbon nanotubes. Extended π-conjugation in these compounds makes them promising candidates for various applications in materials chemistry.

The π bowl sumanene, which is a close relative of corannulene, was first synthesized in 2003 by Toshikazu Hirao and co-workers, Osaka University, Japan. Now the same research group have produced an aryl–aryl coupled sumanene dimer called bisumanenyl. The synthesis was achieved by a palladium-catalyzed Suzuki–Miyura coupling of bromosumanene. The interesting feature of the synthesis is that variable temperature NMR studies indicated a single isomer of bisumanenyl was obtained, despite the inherently rich isomerism of such π bowls. The extension of π-conjugation in bisumanenyl was also shown from the absorption and emission spectra.

This apparently selective synthesis could have implications for the production of further π bowls and their analogues with specific properties for further development of polyaromatic carbon-based materials.

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