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The synthesis and properties of open-hole fullerenes are important research fields in fullerene chemistry Through the holes on the surface of the carbon cage, small molecules can be loaded into the cavity inside the carbon cage, making the porous fullerenes become "molecular containers" At present, the synthesis steps of open-hole fullerenes which can be loaded with small molecules under mild conditions are relatively long, and the small molecules which can be encapsulated are mainly hydrogen and water The practical application of this kind of inclusion complex needs further exploration and development Based on the selective preparation and transformation of fullerene peroxides, ganliangbing research group explored the selective synthesis route of open-hole fullerenes (acc chem Res 2019, 52, 1793-1801) In the previous work, they have synthesized a series of open-ended fullerenes which can be encapsulated in water, but all of them need longer synthesis steps Recently, they found that the open-hole fullerene peroxide 1 obtained in the previous work can react with aniline under different conditions to obtain open-hole fullerene 3 and 4 respectively, that is to say, the open-hole fullerene with 19 membered ring aperture can be obtained from C60 through three-step reaction In addition, they obtained compounds 2a and 2b by changing the reaction conditions, which provided important data for the study of reaction mechanism In this paper, we have studied the properties of the inclusion molecules of open-hole fullerene 3 They found that compound 3 can not only contain water molecules at room temperature and atmospheric pressure, but also oxygen under mild conditions The results showed that 75% of compound 3 was loaded with oxygen when it was stirred for 5 hours at 50 atmospheric pressure and normal temperature The results of kinetic studies show that the half-life of the oxygen releasing process is 73 min at 37 ℃, and the activation energy of the oxygen releasing process is 18.8 kcal · mol-1 The research results of ganliangbing research group show that the porous fullerenes have potential application value in oxygen delivery materials Many medical methods, such as tissue culture in vitro, active oxygen species sterilization and photodynamic therapy of tumor, need sufficient oxygen supply At present, there are many reported oxygen delivery materials, such as modified heme, fluorocarbon and metal peroxides Porous fullerenes as molecular nano materials provide a new research direction for oxygen delivery materials
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The single crystal structures of all the new compounds were analyzed The work was supported by NSFC, the Ministry of science and technology and the Ministry of education.