Belt-Shaped Cyclonaphthylenes.
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.
JST, ERATO, Isobe Degenerate π-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan).
Zhe
Z
Sun
Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan).
Parantap
P
Sarkar
Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan).
Takuya
T
Suenaga
JST, ERATO, Isobe Degenerate π-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan).|Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan).
Sota
S
Sato
JST, ERATO, Isobe Degenerate π-Integration Project and Advanced Institute for Materials Research, Aoba-ku, Sendai 980-8577 (Japan). isobe@m.tohoku.ac.jp.|Advanced Institute for Materials Research and Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan). isobe@m.tohoku.ac.jp.
Hiroyuki
H
Isobe
arenes; atropisomerism; cycloarylenes; macrocycles; nanotubes