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Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment

Author

Listed:
  • Weifan Wang

    (Nanyang Technological University)

  • Fiona Hanindita

    (Nanyang Technological University)

  • Yosuke Hamamoto

    (Nanyang Technological University)

  • Yongxin Li

    (Nanyang Technological University)

  • Shingo Ito

    (Nanyang Technological University)

Abstract

A fully conjugated azacorannulene dimer with a large π-surface (76π system) was successfully synthesized from a fully conjugated bifunctional polycyclic aromatic azomethine ylide. This molecule represents an example of diaza[80]fullerene (C78N2) fragment molecule bearing two internal nitrogen atoms. X-ray crystallography analysis shows its boat-shaped structure with two terminal azacorannulenes bent in the same direction. The molecular shape leads to unique selective association with a dumbbell-shaped C60 dimer (C120) over C60 through shape recognition. Owing to its large π-surface and a narrow HOMO–LUMO gap, the azacorannulene dimer exhibits red fluorescence with a quantum yield of up to 31%. The utilization of the fully conjugated bifunctional azomethine ylide is a powerful method for the bottom-up synthesis of large multiazafullerene fragments, providing a step towards the selective total synthesis of multiazafullerenes.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29106-w
    DOI: 10.1038/s41467-022-29106-w
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    References listed on IDEAS

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    1. 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.
    2. Gonzalo Otero & Giulio Biddau & Carlos Sánchez-Sánchez & Renaud Caillard & María F. López & Celia Rogero & F. Javier Palomares & Noemí Cabello & Miguel A. Basanta & José Ortega & Javier Méndez & Anton, 2008. "Fullerenes from aromatic precursors by surface-catalysed cyclodehydrogenation," Nature, Nature, vol. 454(7206), pages 865-868, August.
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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.

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