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Trichalcogenasupersumanenes and its concave-convex supramolecular assembly with fullerenes

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Listed:
  • Yixun Sun

    (Shaanxi Normal University)

  • Xin Wang

    (Shaanxi Normal University)

  • Bo Yang

    (Shaanxi Normal University)

  • Muhua Chen

    (Shaanxi Normal University)

  • Ziyi Guo

    (Shaanxi Normal University)

  • Yiting Wang

    (Shaanxi Normal University)

  • Ji Li

    (Shaanxi Normal University)

  • Mingyu Xu

    (Shaanxi Normal University)

  • Yunjie Zhang

    (Shaanxi Normal University)

  • Huaming Sun

    (Shaanxi Normal University)

  • Jingshuang Dang

    (Shaanxi Normal University)

  • Juan Fan

    (Shaanxi Normal University)

  • Jing Li

    (Shaanxi Normal University)

  • Junfa Wei

    (Shaanxi Normal University)

Abstract

Synthesis of buckybowls have stayed highly challenging due to the large structural strain caused by curved π surface. In this paper, we report the synthesis and properties of two trichalcogenasupersumanenes which three chalcogen (sulfur or selenium) atoms and three methylene groups bridge at the bay regions of hexa-peri-hexabenzocoronene. These trichalcogenasupersumanenes are synthesized quickly in three steps using an Aldol cyclotrimerization, a Scholl oxidative cyclization, and a Stille type reaction. X-ray crystallography analysis reveals that they encompass bowl diameters of 11.06 Å and 11.35 Å and bowl depths of 2.29 Å and 2.16 Å for the trithiasupersumanene and triselenosupersumanene, respectively. Furthermore, trithiasupersumanene derivative with methyl chains can form host-guest complexes with C60 or C70, which are driven by concave-convex π ⋯ π interactions and multiple C–H ⋯ π interactions between bowl and fullerenes.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-39086-0
    DOI: 10.1038/s41467-023-39086-0
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    References listed on IDEAS

    as
    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. Qitao Tan & Shuhei Higashibayashi & Sangita Karanjit & Hidehiro Sakurai, 2012. "Enantioselective synthesis of a chiral nitrogen-doped buckybowl," Nature Communications, Nature, vol. 3(1), pages 1-6, January.
    3. 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.
    4. Yuki Tanaka & Norihito Fukui & Hiroshi Shinokubo, 2020. "as-Indaceno[3,2,1,8,7,6-ghijklm]terrylene as a near-infrared absorbing C70-fragment," Nature Communications, Nature, vol. 11(1), pages 1-7, December.
    5. Juan Ramon Sanchez-Valencia & Thomas Dienel & Oliver Gröning & Ivan Shorubalko & Andreas Mueller & Martin Jansen & Konstantin Amsharov & Pascal Ruffieux & Roman Fasel, 2014. "Controlled synthesis of single-chirality carbon nanotubes," Nature, Nature, vol. 512(7512), pages 61-64, August.
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