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Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes

Author

Listed:
  • Shunpei Hitosugi

    (Tohoku University, Aoba-ku, Sendai 980-8578, Japan.)

  • Waka Nakanishi

    (Tohoku University, Aoba-ku, Sendai 980-8578, Japan.)

  • Takashi Yamasaki

    (Tohoku University, Aoba-ku, Sendai 980-8578, Japan.)

  • Hiroyuki Isobe

    (Tohoku University, Aoba-ku, Sendai 980-8578, Japan.)

Abstract

The bottom-up synthesis of hoop-shaped aromatic hydrocarbons is currently attracting interest, because they can serve as finite models of single-wall carbon nanotubes (SWNTs). Models for chiral (n,m)-SWNTs, particularly those with optical activity, have not been synthesized but are of special interest owing to their anomalous helical network of sp2-carbons. Here we show that finite model compounds for (12,8)-, (11,9)- and (10,10)-SWNTs are synthetically accessible by a stepwise macrocyclization of [4]phenacene, a compound that bears fused benzene rings in a zigzag arrangement, and we can isolate and identify all the isomers including the enantiomers with (P)- and (M)-helicity. The complete isolation and identification of the model compounds led to the first examination of the stereo-disproportionation of chiral SWNT models, which encourages the future studies on asymmetric induction for the synthesis.

Suggested Citation

  • Shunpei Hitosugi & Waka Nakanishi & Takashi Yamasaki & Hiroyuki Isobe, 2011. "Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes," Nature Communications, Nature, vol. 2(1), pages 1-5, September.
    • Handle: RePEc:nat:natcom:v:2:y:2011:i:1:d:10.1038_ncomms1505
    DOI: 10.1038/ncomms1505
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    Cited by:

    1. Jiaqi Liang & Shuai Lu & Yang Yang & Yun-Jia Shen & Jin-Ku Bai & Xin Sun & Xu-Lang Chen & Jie Cui & Ai-Jiao Guan & Jun-Feng Xiang & Xiaopeng Li & Heng Wang & Yu-Dong Yang & Han-Yuan Gong, 2023. "Thermally-induced atropisomerism promotes metal-organic cage construction," Nature Communications, Nature, vol. 14(1), pages 1-12, December.

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