Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 21, Pages 8086-8089Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja201267t
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Funding
- MEXT, Japan [22000008]
- Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [22000008] Funding Source: KAKEN
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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-pi-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.
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