Perfluorocycloparaphenylenes: Fully fluorinated carbon nanorings by Ni-mediated one-pot synthesis

21 October 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 have remained elusive so far, 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) were determined by X-ray crystallography to confirm their tubular alignment. Photophysical and electrochemical measurements revealed that PF[n]CPPs (n = 10, 12) exhibit wide HOMO–LUMO gaps, high electron affinity, and strong phosphorescence at low temperature. PFCPPs are not only useful as electron-accepting organic semiconductors but can also be used for accelerating the creation of topologically unique molecular nanocarbon materials.

Keywords

cycloparaphenylenes
perfluoroarenes
carbon nanorings
molecular nanocarbons

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