Perfluorocycloparaphenylenes

Hiroki Shudo, Motonobu Kuwayama, Masafumi Shimasaki, Taishi Nishihara, Youhei Takeda, Nobuhiko Mitoma, Takuya Kuwabara, Akiko Yagi, Yasutomo Segawa () and Kenichiro Itami ()
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Hiroki Shudo: Nagoya University
Motonobu Kuwayama: Nagoya University
Masafumi Shimasaki: Kyoto University
Taishi Nishihara: Kyoto University
Youhei Takeda: Osaka University
Nobuhiko Mitoma: RIKEN Center for Emergent Matter Science
Takuya Kuwabara: Nagoya University
Akiko Yagi: Nagoya University
Yasutomo Segawa: Nagoya University
Kenichiro Itami: Nagoya University

Nature Communications, 2022, vol. 13, issue 1, 1-6

Abstract: Abstract 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.

Date: 2022
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DOI: 10.1038/s41467-022-31530-x

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