FeCl3-mediated synthesis of fullerenyl esters as low-LUMO acceptors for organic photovoltaic devices.

Org Lett

Fullerene Development Group, Performance Products Division, Mitsubishi Chemical Corporation, 1-1 Kurosakishiroishi, Yahatanishi-ku, Kitakyushu 806-0004, Japan.

Published: July 2012

C(60) reacted with aromatic and aliphatic carboxylic acids in the presence of inexpensive FeCl(3) at room temperature to produce hydroxyfullerenyl esters C(60)(OCOR)(OH) in up to 68% isolated yield. The hydroxyl group was utilized in functional group transformations to obtain a diester derivative C(60)(OCOAr)(OCOPh) (Ar = 2,6-xylyl) and a siloxyl derivative C(60)(OCOAr)(OSiMe(3)). The diester and siloxyl derivatives were found to possess low-lying LUMO levels were utilized in organic photovoltaic devices showing 1.3% power conversion efficiency.

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http://dx.doi.org/10.1021/ol301186uDOI Listing

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