(6,6)Carbon Nanobelt as a Useful Synthetic Tool for the Construction of Cycloiptycenes

Iptycenes have a structure in which aromatic ring is condensed into a bicyclooctatriene skeleton, as represented by triptycene. As a rigid three-dimensional π-conjugated molecule group, they form attractive target molecules. However, it is not easy to synthesize iptycenes from available small molecules. In particular, cycloiptycene, in which triptycene is condensed to form a ring shape, has never been synthesized. Segawa, Itami and co-workers have succeeded in the synthesis of each of the cycloiptycene derivatives in one step from (6,6)carbon nanobelt.¹⁾ It was revealed that (6,6)carbon nanobelt²⁾ reacted as a diene in the Diels–Alder reaction with arynes and alkynes like diphenylacetylene. The Diels–Alder reaction takes place at the six central benzene rings of (6,6)carbon nanobelt. Using this method, a variety of cycloiptycenes can be easily synthesized.

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References

• 1) Synthesis of Cycloiptycenes from Carbon Nanobelts
  • H. Shudo, M. Kuwayama, Y. Segawa, K. Itami, Chem. Sci. 2020, 11, 6775.
• 2) Synthesis of a Carbon Nanobelt
  • G. Povie, Y. Segawa, T. Nishihara, Y. Miyauchi, K. Itami, Science 2017, 356, 172.

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