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Synfacts 2009(2): 0156-0156  
DOI: 10.1055/s-0028-1087492
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Regioselective 1,4-Substitution of [60]Fullerenes

Contributor(s):Timothy M. Swager, Fei Wang
Y. Matsuo*, A. Iwashita, Y. Abe, C.-Z. Li, K. Matsuo, M. Hashiguchi, E. Nakamura*
Japan Science and Technology Agency, Tokyo and the University of Tokyo, Japan
Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction
J. Am. Chem. Soc.  2008,  130:  15429-15436  
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Publication History

Publication Date:
22 January 2009 (online)

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Key words

fullerenes - regioselectivity - n-type materials

Significance

The authors report a two-step re­gioselective synthesis of 1,4-di(organo)[60]fulle-renes. In the first step, DMF-assisted monoaddition of silylmethyl Grignard reagent to [60]fulle-renes produces (organo)(hydro)[60]fullerenes. Deprotonation and alkylation in the second step generates di(organo)[60]fullerenes with various functional groups, whose crystal structures, ­electrochemical and thermal properties have been studied.

Comment

The synthetic difficulties of 1,4-substituted 58π-electron [60]fullerenes make them less explored than their 1,2-substituted counterparts such as PCBM. This efficient approach with high regioselectivity, simple starting materials and easy procedures may lead to new opportunities to the research on fullerene based n-type materials.

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