Copper-MediatedThree-Component Synthesis of DiversePerfluoroalkylated Fullerenes

The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C<sub>60</sub>. Furthermore, the challenges posed by C–F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.

Publication Details

Journal
Figshare
Published
2025-01-28
DOI
https://doi.org/10.1021/acs.joc.4c02753.s001
Primary Topic
Fullerene Chemistry and Applications
Type
article
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article

Copper-MediatedThree-Component Synthesis of DiversePerfluoroalkylated Fullerenes

Figshare
Fullerene Chemistry and Applications
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Copper-MediatedThree-Component Synthesis of DiversePerfluoroalkylated Fullerenes

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Abstract

The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C<sub>60</sub>. Furthermore, the challenges posed by C–F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.

Figshare
Openalex Percentile: Top 69%
Fullerene Chemistry and Applications
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Copper-MediatedThree-Component Synthesis of DiversePerfluoroalkylated Fullerenes · Figshare (2025) | TGRS Research Map | TGRS