Synthesis of Cycloiptycenes from Carbon Nanobelt

Hiroki Shudo, Motonobu Kuwayama, Yasutomo Segawa*, Kenichiro Itami*

“Synthesis of Cycloiptycenes from Carbon Nanobelt”
Chem. Sci. 2020, accepted. DOI:10.1039/D0SC01909G


The synthesis of cycloiptycene derivatives was achieved in each one step from (6,6)carbon nanobelt. It was revealed that the carbon nanobelt was reacted as a diene in the Diels–Alder reaction with arynes and alkynes. Structures of all products were identified by X-ray crystallography to confirm that the Diels–Alder reactions took place at the six central benzene rings of the carbon nanobelt. DFT calculations indicated that the release of strain energy is the driving force to proceed the Diels– Alder reaction. By using this method, we have successfully synthesized cyclotetracosipticene, the largest iptycene ever synthesized.

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