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Updated: Apr 29, 2026
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Synthesis of open-cage ketolactam derivatives of fullerene C60 encapsulating a hydrogen molecule
Yoshifumi Hashikawa1, Michihisa Murata, Atsushi Wakamiya
1Institute for Chemical Research, Kyoto University , Uji, Kyoto 611-0011, Japan.
Abstract:
A novel open-cage fullerene C60 derivative having a bis(hemiketal) moiety was synthesized by the reaction of C60-N-MEM-ketolactam (MEM: 2-methoxyethoxymethyl) with N-methylmorpholine N-oxide in the presence of water. The structure was clearly determined by single crystal X-ray analysis. Further enlargement of the opening was performed by treatment with trifluoroacetic anhydride to give the tetraketo derivative having a 15-membered ring opening. For H2-insertion into the cage, the derivative was exposed to a high pressure of H2. After the encapsulation, the opening size was reduced to the original one while keeping the hydrogen molecule inside the cage. This compound can be a possible precursor for endohedral azafullerenes encapsulating a hydrogen molecule.
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