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Nitrogen-embedded buckybowl and its assembly with C60

Author

Listed:
  • Hiroki Yokoi

    (Graduate School of Engineering, Nagoya University)

  • Yuya Hiraoka

    (Graduate School of Engineering, Nagoya University)

  • Satoru Hiroto

    (Graduate School of Engineering, Nagoya University)

  • Daisuke Sakamaki

    (Graduate School of Engineering, Kyoto University)

  • Shu Seki

    (Graduate School of Engineering, Kyoto University)

  • Hiroshi Shinokubo

    (Graduate School of Engineering, Nagoya University)

Abstract

Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium-catalysed intramolecular coupling. The electron-donating nature and curved π surface of the azabuckybowl enable its tight association with C60 in solution and solid states. High charge mobility is observed for the azabuckybowl/C60 assembly. This compound may be of interest in the fields of curved π systems as fullerene hosts, anisotropic π donors and precursors to nitrogen-containing nanocarbon materials.

Suggested Citation

  • Hiroki Yokoi & Yuya Hiraoka & Satoru Hiroto & Daisuke Sakamaki & Shu Seki & Hiroshi Shinokubo, 2015. "Nitrogen-embedded buckybowl and its assembly with C60," Nature Communications, Nature, vol. 6(1), pages 1-9, November.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms9215
    DOI: 10.1038/ncomms9215
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    Cited by:

    1. Yixun Sun & Xin Wang & Bo Yang & Muhua Chen & Ziyi Guo & Yiting Wang & Ji Li & Mingyu Xu & Yunjie Zhang & Huaming Sun & Jingshuang Dang & Juan Fan & Jing Li & Junfa Wei, 2023. "Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Weifan Wang & Fiona Hanindita & Yosuke Hamamoto & Yongxin Li & Shingo Ito, 2022. "Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment," Nature Communications, Nature, vol. 13(1), pages 1-7, December.

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