title: 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.
abstract: Oxidation 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.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
authors.forename: Yuming
authors.initials: Y
authors.lastname: Yu
authors.forename: Xiang
authors.initials: X
authors.lastname: Xie
authors.forename: Tong
authors.initials: T
authors.lastname: Zhang
authors.forename: Shuming
authors.initials: S
authors.lastname: Liu
authors.forename: Yuanhua
authors.initials: Y
authors.lastname: Shao
authors.forename: Liangbing
authors.initials: L
authors.lastname: Gan
authors.forename: Yuliang
authors.initials: Y
authors.lastname: Li