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Synthesis of open-cage ketolactam derivatives of fullerene C60 encapsulating a hydrogen molecule.

水素分子を内包するフラーレンC60開口型ケトラクタム誘導体の合成

other not specified not assessed

Abstract

A new open-cage C60 fullerene derivative bearing a bis(hemiketal) unit was obtained through reaction of C60-N-MEM-ketolactam (MEM: 2-methoxyethoxymethyl) with N-methylmorpholine N-oxide in the presence of water, with the structure confirmed by single-crystal X-ray diffraction. The orifice was subsequently expanded to a 15-membered ring by treatment with trifluoroacetic anhydride, yielding a tetraketo derivative. Exposure of this compound to high-pressure H2 gas allowed encapsulation of a single hydrogen molecule within the cage. Following encapsulation, the opening was contracted back to its original dimensions while retaining the H2 inside. The resulting compound represents a potential precursor for the preparation of endohedral azafullerenes that contain an encapsulated hydrogen molecule.

Mechanism

High-pressure H2 gas was used to insert a hydrogen molecule through an enlarged 15-membered ring orifice of an open-cage C60 derivative; subsequent chemical reduction of the opening size trapped the H2 molecule inside the fullerene cage.

Bibliographic

Authors
Hashikawa Y, Murata M, Wakamiya A, Murata Y
Journal
Org Lett
Year
2014 (2014-06-06)
PMID
24828793
DOI
10.1021/ol501113y

Tags

Delivery context

The delivery route is not clearly identifiable from this paper. For hydrogen intake, inhalation is the most efficient route; inhalation, however, carries explosion risk (empirical LFL of 10%; high-concentration devices are not recommended).

Safety notes

The delivery route is not clearly identifiable from this paper. For hydrogen intake, inhalation is the most efficient route; inhalation, however, carries explosion risk (empirical LFL of 10%; high-concentration devices are not recommended).

See also:

Cite as: H2 Papers — PMID 24828793. https://h2-papers.org/en/papers/24828793
Source: PubMed PMID 24828793