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A self-complementary macrocycle by a dual interaction system

Author

Listed:
  • Yuta Sawanaka

    (Tokyo Institute of Technology)

  • Masahiro Yamashina

    (Tokyo Institute of Technology)

  • Hiroyoshi Ohtsu

    (Tokyo Institute of Technology)

  • Shinji Toyota

    (Tokyo Institute of Technology)

Abstract

Self-complementary assembly is one of the most promising phenomena for the formation of discrete assemblies, e.g., proteins and capsids. However, self-complementary assembly based on multiple host-guest systems has been scarcely reported due to the difficulty in controlling each assembly. Herein, we report a dual interaction system in which the key assembly direction is well regulated by both π-π stacking and hydrogen bonding to construct a self-complementary macrocycle. Continuous host-guest behavior of anthracene-based molecular tweezers during crystallization leads to successful construction of a cyclic hexamer, which is reminiscent of Kekulé’s monkey model. Furthermore, the cyclic hexamer in a tight and triple-layered fashion shows hierarchical assembly into cuboctahedron and rhombohedral assemblies in the presence of trifluoroacetic acid. Our findings would be potentially one of metal-free strategies for constructing anthracene-based supramolecular assemblies with higher-order structure.

Suggested Citation

  • Yuta Sawanaka & Masahiro Yamashina & Hiroyoshi Ohtsu & Shinji Toyota, 2022. "A self-complementary macrocycle by a dual interaction system," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33357-y
    DOI: 10.1038/s41467-022-33357-y
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    References listed on IDEAS

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    1. Gongpu Zhao & Juan R. Perilla & Ernest L. Yufenyuy & Xin Meng & Bo Chen & Jiying Ning & Jinwoo Ahn & Angela M. Gronenborn & Klaus Schulten & Christopher Aiken & Peijun Zhang, 2013. "Mature HIV-1 capsid structure by cryo-electron microscopy and all-atom molecular dynamics," Nature, Nature, vol. 497(7451), pages 643-646, May.
    2. Kang Cai & Mark C. Lipke & Zhichang Liu & Jordan Nelson & Tao Cheng & Yi Shi & Chuyang Cheng & Dengke Shen & Ji-Min Han & Suneal Vemuri & Yuanning Feng & Charlotte L. Stern & William A. Goddard & Mich, 2018. "Molecular Russian dolls," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    3. Satomi Niwa & Long-Jiang Yu & Kazuki Takeda & Yu Hirano & Tomoaki Kawakami & Zheng-Yu Wang-Otomo & Kunio Miki, 2014. "Structure of the LH1–RC complex from Thermochromatium tepidum at 3.0 Å," Nature, Nature, vol. 508(7495), pages 228-232, April.
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    Cited by:

    1. Sha Bai & Lu-Wen Zhang & Zi-Hang Wei & Fang Wang & Qing-Wen Zhu & Ying-Feng Han, 2024. "Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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