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Synthesis and assembly of extended quintulene

Author

Listed:
  • Hao Hou

    (Xiamen University)

  • Xin-Jing Zhao

    (Xiamen University)

  • Chun Tang

    (Xiamen University)

  • Yang-Yang Ju

    (Xiamen University)

  • Ze-Ying Deng

    (Xiamen University)

  • Xin-Rong Wang

    (Xiamen University)

  • Liu-Bin Feng

    (Xiamen University)

  • Dong-Hai Lin

    (Xiamen University)

  • Xu Hou

    (Xiamen University)

  • Akimitsu Narita

    (Max Planck Institute for Polymer Research)

  • Klaus Müllen

    (Max Planck Institute for Polymer Research
    Johannes Gutenberg-Universitat Mainz)

  • Yuan-Zhi Tan

    (Xiamen University)

Abstract

Quintulene, a non-graphitic cycloarene with fivefold symmetry, has remained synthetically elusive due to its high molecular strain originating from its curved structure. Here we report the construction of extended quintulene, which was unambiguously characterized by mass and NMR spectroscopy. The extended quintulene represents a naturally curved nanocarbon based on its conical molecular geometry. It undergoes dimerization in solution via π−π stacking to form a metastable, but isolable bilayer complex. Thermodynamic and kinetic characterization reveals the dimerization process as entropy-driven and following second-order kinetics with a high activation energy. These findings provide a deeper understanding of the assembly of conical nanocarbons. Comparison of optical properties of monomer and dimer points toward a H-type interlayer coupling in the dimer.

Suggested Citation

  • Hao Hou & Xin-Jing Zhao & Chun Tang & Yang-Yang Ju & Ze-Ying Deng & Xin-Rong Wang & Liu-Bin Feng & Dong-Hai Lin & Xu Hou & Akimitsu Narita & Klaus Müllen & Yuan-Zhi Tan, 2020. "Synthesis and assembly of extended quintulene," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-17691-7
    DOI: 10.1038/s41467-020-17691-7
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