Synthesis of a Series of Malonic Diester–Introduced Fullerene Derivatives

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.

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GRAPHICAL ABSTRACT

Keywords:

• Bingel reaction
• fullerene
• malonic diester
• solubility parameter

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.