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Radical Reaction Of (60)fullerene With Phosphorus Compounds Mediated By Manganese(iii) Acetate

Posted on:2011-05-19Degree:MasterType:Thesis
Country:ChinaCandidate:C Z WangFull Text:PDF
GTID:2191330338491891Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Among the myriad of fullerene derivatives reported today, only a limited number of fullerene compounds containing a phosphorus atom are known. Rare examples on phosphorylated fullerene derivatives with the phosphorus atom attached directly to the fullerene skeleton have been described and only limited to hydrofullerene Some of the phosphorus-containing fullerene derivatives were shown to have active biological activities and optical properties. Therefore, it is demanding to achieve the synthesis of other type of phosphorylated fullerene derivatives for the purpose of diversity and potential application.We have successfully realized the reaction of C60 with phosphorus-centered radicals, generated from the phosphonates or phosphine oxide by Mn(OAc)3. Depending on the reaction conditions, three different types of phosphorylated fullerene derivatives, that is, singly-bonded fullerene dimers R2(O)PC60-C60P(O)R2, hydrofullerenes R2(O)PC60H, and acetoxylated fullerenes R2(O)PC60OAc, could be selectively obtained. Interestingly, the individual meso and racemic isomers of the singly-bonded fullerene dimers R2(O)PC60-C60P(O)R2 could be separated out for the first time. Furthermore, interconversions among the three types of phosphorylated fullerene derivatives have also been achieved. It was found that both singly-bonded dimers R2(O)PC60-C60P(O)R2 and hydrofullerenes R2(O)PC60H could be converted efficiently to acetoxylated fullerenes R2(O)PC60OAc, and hydrofullerenes R2(O)PC60H could be transformed to singly-bonded dimers R2(O)PC60-C60P(O)R2. dimers R2(O)PC60-C60P(O)R2 could be transformed to hydrofullerenes R2(O)PC60H in presence of the phosphonates or phosphine oxide. Possible reaction mechanisms were proposed to explain the formation of the fullerene products.
Keywords/Search Tags:fullerene, radicals, phosphonates, phosphine oxide, Mn(OAc)3, singly-bonded fullerene dimers, hydrofullerenes, acetoxylated fullerene
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