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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 2
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Original Articles

Synthesis of a Series of Malonic Diester–Introduced Fullerene Derivatives

, , , , &
Pages 275-279 | Received 12 Apr 2013, Published online: 29 Oct 2013
 

Abstract

A facile preparation method for derivatization of fullerene through the Bingel reaction was introduced. A series of fullerene derivatives, to which malonic diester with different substituents were introduced, were systematically synthesized by Bingel reaction. Malonic diester could be added to fullerene at room temperature in the presence of iodine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and various substituents such as phenyl, hexyl, thienyl, and pyrenyl were introduced into both sides of the malonic diester. As a result, 17 systematic variations were synthesized. The solubility parameters of the obtained fullerene derivatives calculated by the method reported by Fedors were in the range of 33 to 43 (J cm−3)1/2.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. The authors are grateful to Mr. Baba for the capable assistance.

Notes

a The solubility parameters.

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