Buckybowl-Type Fragment of C70 Synthesized

  • Author: ChemistryViews.org
  • Published: 30 April 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Buckybowl-Type Fragment of C<sub>70</sub> Synthesized

Bowl-shaped fragments of fullerenes, so-called buckybowls, are useful precursors for the synthesis of fullerenes and also have interesting properties themselves. Some fragments of C60, such as corannulene, are well studied. In contrast, there is a lack of methods for the synthesis of bowl-shaped C70 fragments.


Jishan Wu, National University of Singapore and Tianjin University, Fuzhou, China, and colleagues have synthesized a bowl-shaped arylated derivative of a C70 fragment, dicyclopenta[4,3,2,1-ghi:4′,3′,2′,1′-pqr]perylene (pictured). The team used a solution-phase synthesis starting from 3-formylperylene. Friedel–Crafts alkylations were used close the five-membered rings and brominations followed by Suzuki couplings were used to introduce stabilizing aryl substituents.


The resulting arylated C70-fragment is stable and has a bowl shape, which was shown using X-ray crystallography. NMR spectroscopy showed that the compound has an overall antiaromatic character, which is unusual for a buckybowl. The NMR measurements also showed that the bowl undergoes rapid inversion at room temperature.


 

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