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Synthesis of inter-[60]fullerene conjugates with inherent chirality

Author

Listed:
  • Yoshifumi Hashikawa

    (Kyoto University, Uji)

  • Shu Okamoto

    (Kyoto University, Uji)

  • Yasujiro Murata

    (Kyoto University, Uji)

Abstract

Coalescence of [60]fullerenes potentially produces hypothetical nanocarbon assemblies with non-naturally occurring topologies. Since the discovery of [60]fullerene in 1985, coalesced [60]fullerene oligomers have only been observed as transient species by transmission electron microscopy during an oligomerization process under a high electron acceleration voltage. Herein, we showcase the rational synthesis of covalent assemblies consisting of inherently chiral open-[60]fullerenes. The crystallographic analyses unveiled double-caged structures of non-conjugated and conjugated inter-[60]fullerene hybrids, in which the two [60]fullerene cages are bounds to each other through a covalent linkage. The former one further assembles via a heterochiral recognition so that four carbon cages are arranged in a tetrahedral manner both in solution and solid state. Reflecting radially-conjugated double π-surface nature, the inter-[60]fullerene conjugate exhibits strong electronic communication in its reduced states, intense absorption behavior, and chiroptical activity with a dissymmetry factor of 0.21 (at 674 nm) which breaks the record for known chiral organic molecules.

Suggested Citation

  • Yoshifumi Hashikawa & Shu Okamoto & Yasujiro Murata, 2024. "Synthesis of inter-[60]fullerene conjugates with inherent chirality," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-44834-x
    DOI: 10.1038/s41467-024-44834-x
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    References listed on IDEAS

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    1. Brian W. Smith & Marc Monthioux & David E. Luzzi, 1998. "Encapsulated C60 in carbon nanotubes," Nature, Nature, vol. 396(6709), pages 323-324, November.
    2. Guan-Wu Wang & Koichi Komatsu & Yasujiro Murata & Motoo Shiro, 1997. "Synthesis and X-ray structure of dumb-bell-shaped C120," Nature, Nature, vol. 387(6633), pages 583-586, June.
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