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Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes
Yu, Yuming1,2; Xie, Xiang1,3; Zhang, Tong1,3; Liu, Shuming1,2; Shao, Yuanhua1,3; Gan, Liangbing1,3; Li, Yuliang1,2
2011-12-16
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume76Issue:24Pages:10148-10153
AbstractOxidation of the fullerenediol C-60(OH)(2)(O)(OAc)-(OOtBu)(3) with PhI(OAc)(2) yields the open-cage fullerene derivative C-60(O)(2)(O)(OAc)(OOtBu)(3) 2 with an 11-membered orifice. Compound 2 reacts with aniline to form a new open-cage derivative with a 14-membered orifice, which yields an 18-membered open-cage fullerene derivative upon addition of another molecule of aniline. Two different types of aniline derivatives with either electron-donating or electron-withdrawing substituents can be added sequentially, affording an unsymmetrical moiety in the open-cage structure. Reduction potentials of the 18-membered open-cage fullerene derivatives can be fine-tuned by changing the substituents on the aniline. The results provide new insights about the mechanism of open-cage reactions of fullerene-mixed peroxide.
DOI10.1021/jo202014q
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000297715900027
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:15[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/73140
Collection中国科学院化学研究所
Corresponding AuthorGan, Liangbing
Affiliation1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100080, Peoples R China
2.Chinese Acad Sci, CAS Key Lab Organ Solids, Inst Chem, Beijing 100080, Peoples R China
3.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Yu, Yuming,Xie, Xiang,Zhang, Tong,et al. Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(24):10148-10153.
APA Yu, Yuming.,Xie, Xiang.,Zhang, Tong.,Liu, Shuming.,Shao, Yuanhua.,...&Li, Yuliang.(2011).Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes.JOURNAL OF ORGANIC CHEMISTRY,76(24),10148-10153.
MLA Yu, Yuming,et al."Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes".JOURNAL OF ORGANIC CHEMISTRY 76.24(2011):10148-10153.
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