First Synthesis and Characterization of CH4@C60

The endohedral fullerene CH4@C60, in which each C60 fullerene cage encapsulates a single methane molecule, has been synthesized for the first time. Methane is the first organic molecule, as well as the largest, to have been encapsulated in C60 to date. The key orifice contraction step, a photochemic...

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Bibliographic Details
Published in:Angewandte Chemie 2019-04, Vol.131 (15), p.5092-5097
Main Authors: Bloodworth, Sally, Sitinova, Gabriela, Alom, Shamim, Vidal, Sara, Bacanu, George R., Elliott, Stuart J., Light, Mark E., Herniman, Julie M., Langley, G. John, Levitt, Malcolm H., Whitby, Richard J.
Format: Article
Language:English
Subjects:
Benzene
Buckminsterfullerene
Cages
Carbon
Chemical synthesis
Chemistry
Contraction
Crystal structure
Electron density
Encapsulation
Endohedrale Fullerene
Fullerenes
Massenspektrometrie
Methane
Molecular structure
Nickel
NMR-Spectroskopie
Orifices
Photochemicals
Röntgenbeugung
Synthesemethoden
Vapor phases
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Summary:The endohedral fullerene CH4@C60, in which each C60 fullerene cage encapsulates a single methane molecule, has been synthesized for the first time. Methane is the first organic molecule, as well as the largest, to have been encapsulated in C60 to date. The key orifice contraction step, a photochemical desulfinylation of an open fullerene, was completed, even though it is inhibited by the endohedral molecule. The crystal structure of the nickel(II) octaethylporphyrin/ benzene solvate shows no significant distortion of the carbon cage, relative to the C60 analogue, and shows the methane hydrogens as a shell of electron density around the central carbon, indicative of the quantum nature of the methane. The 1H spin‐lattice relaxation times (T1) for endohedral methane are similar to those observed in the gas phase, indicating that methane is freely rotating inside the C60 cage. The synthesis of CH4@C60 opens a route to endofullerenes incorporating large guest molecules and atoms. Durch photochemische Desulfinylierung eines offenen Fullerens wurde endohedrales CH4@C60 synthetisiert. Methan ist wesentlich größer als bislang in C60 eingeschlossene Moleküle und gehört zu den größtmöglichen Molekülen, die sich in dieses Fulleren einschließen lassen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201900983