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. [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.]