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Sun Z, Sarkar P, Suenaga T, et al. Belt-Shaped Cyclonaphthylenes. Angew Chem Int Ed Engl. 2015;54(43):12800-4doi: 10.1002/anie.201506424.
Sun, Z., Sarkar, P., Suenaga, T., Sato, S., & Isobe, H. (2015). Belt-Shaped Cyclonaphthylenes. Angewandte Chemie (International ed. in English), 54(43), 12800-4. https://doi.org/10.1002/anie.201506424
Sun, Zhe, et al. "Belt-Shaped Cyclonaphthylenes." Angewandte Chemie (International ed. in English) vol. 54,43 (2015): 12800-4. doi: https://doi.org/10.1002/anie.201506424
Sun Z, Sarkar P, Suenaga T, Sato S, Isobe H. Belt-Shaped Cyclonaphthylenes. Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12800-4. doi: 10.1002/anie.201506424. Epub 2015 Sep 01. PMID: 26333160.
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Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12800-4. doi: 10.1002/anie.201506424. Epub 2015 Sep 01.

Belt-Shaped Cyclonaphthylenes.

Angewandte Chemie (International ed. in English)

Zhe Sun, Parantap Sarkar, Takuya Suenaga, Sota Sato, Hiroyuki Isobe

Affiliations

  1. JST, ERATO, Isobe Degenerate ?-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan).
  2. Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan).
  3. JST, ERATO, Isobe Degenerate ?-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan). [email protected].
  4. Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan). [email protected].

PMID: 26333160 DOI: 10.1002/anie.201506424

Abstract

The recent development of cyclo-para-phenylenes has demonstrated the feasibility of radial π systems in nanohoop structures, especially in the crystalline state. However, in contrast to macrocyclic molecules with benzene units, which have a several-decades-long history, macrocycles composed solely of naphthylene units (the smallest acene) have been much less explored. Although two examples of cyclonaphthylenes have been reported to date, neither possesses a radial π system. We herein report the first example of belt-shaped cyclonaphthylenes with curved π systems. The molecule, [8]cyclo-amphi-naphthylene, is linked at the 2,6-positions of the naphthylene units, thus affording belt-shaped molecules. Although the molecular structures are flexible, which allows for rotation of the naphthylene units in solution, they can be rigidified with the aid of methylene bridges to afford persistent molecular structures in solution.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arenes; atropisomerism; cycloarylenes; macrocycles; nanotubes

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