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Perfluorocycloparaphenylenes

Perfluorocycloparaphenylenes

Hiroki Shudo, Motonobu Kuwayama, Masafumi Shimasaki, Taishi Nishihara, Youhei Takeda, Nobuhiko Mitoma, Takuya Kuwabara, Akiko Yagi, Yasutomo Segawa* and Kenichiro Itami*

Nature Communications 2022, 13: 3713. DOI: 10.1038/s41467-022-31530-x

Perfluorinated aromatic compounds, the so-called perfluoroarenes, are widely used in materials science owing to their high electron affinity and characteristic intermolecular interactions. However, methods to synthesize highly strained perfluoroarenes are limited, which greatly limits their structural diversity. Herein, we report the synthesis and isolation of perfluorocycloparaphenylenes (PFCPPs) as a class of ring-shaped perfluoroarenes. Using macrocyclic nickel complexes, we succeeded in synthesizing PF[n]CPPs (n = 10, 12, 14, 16) in one-pot without noble metals. The molecular structures of PF[n]CPPs (n = 10, 12, 14) were determined by X-ray crystallography to confirm their tubular alignment. Photophysical and electrochemical measurements revealed that PF[n]CPPs (n = 10, 12, 14) exhibited wide HOMO–LUMO gaps, high reduction potentials, and strong phosphorescence at low temperature. PFCPPs are not only useful as electron-accepting organic materials but can also be used for accelerating the creation of topologically unique molecular nanocarbon materials.

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