1307316-82-0Relevant academic research and scientific papers
A scalable synthesis of methano[60]fullerene and congeners by the oxidative cyclopropanation reaction of silylmethylfullerene
Zhang, Ying,Matsuo, Yutaka,Li, Chang-Zhi,Tanaka, Hideyuki,Nakamura, Eiichi
, p. 8086 - 8089 (2011)
1,2-Dihydromethano[60]fullerene and its congeners have attracted much interest, but they have been synthesized only in very low yields because of several insurmountable problems. A new three-stage synthesis involving addition of a silylmethylmagnesium chloride to [60]- and [70]fullerene and oxidation of the anionic intermediate with CuCl2 afforded the methano[60]- and methano[70]fullerenes in 90% and 70% overall yield, respectively. The reaction with 1,4-diorgano[60]fullerene also proceeded smoothly to give a diastereomerically pure 56-π-electron fullerene that has a higher LUMO level than the parent fullerene and gave a higher open-circuit voltage and better power conversion efficiency when fabricated into an organic photovoltaic device.
