Oxygen‐Delivery Materials: Synthesis of an Open‐Cage Fullerene Derivative Suitable for Encapsulation of H2O2 and O2

An open‐cage [60]fullerene was prepared through a multiple‐step sequence based on peroxide‐mediated cage‐opening reactions. Key steps include repeated C60‐sensitized singlet‐oxygen oxidation of electron‐rich amino enol double bonds to form two lactone and two lactam moieties on the rim of the orific...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-10, Vol.57 (43), p.14144-14148
Main Authors: Li, Yanbang, Lou, Ning, Xu, Dan, Pan, Changwang, Lu, Xing, Gan, Liangbing
Format: Article
Language:English
Subjects:
Amides
Buckminsterfullerene
Cages
Encapsulation
Fullerenes
Hydrogen peroxide
molecular containers
open-cage fullerenes
Orifices
Oxidation
Oxygen
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Summary:An open‐cage [60]fullerene was prepared through a multiple‐step sequence based on peroxide‐mediated cage‐opening reactions. Key steps include repeated C60‐sensitized singlet‐oxygen oxidation of electron‐rich amino enol double bonds to form two lactone and two lactam moieties on the rim of the orifice. Single‐crystal X‐ray analysis shows that the 22‐membered orifice has an ellipsoid shape with the major axis at 6.7 Å and the minor axis at 3.5 Å. Encapsulation of H2O2 was observed under atmospheric pressure at room temperature. Oxygen is also effectively trapped during the process. Genie in a bottle: An open‐cage [60]fullerene was prepared through a multiple‐step sequence based on peroxide‐mediated cage‐opening reactions. There are two lactone and two lactam moieties on the rim of the 22‐membered orifice, which has an ellipse shape with the major axis at 6.7 Å and the minor axis at 3.5 Å. Efficient encapsulation of H2O2 and O2 was achieved under atmospheric pressure at room temperature.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808926