Abstract
Discovery of an efficient, practical, and flexible synthetic method to produce various important electron acceptors for low-cost organic photovoltaics (OPVs) is highly desirable. Although the most commonly used acceptor materials, such as PC61BM, PC71BM, IC60BA, bisPC61BM have been proved to be promising for the OPVs, they are still very expensive mainly due to their low production yields and limited synthetic methods. Herein, we report an unprecedented and innovative synthetic method of a variety of fullerene mono- and biscycloadducts by using manganese powder as a promotor. The reaction of fullerenes with various dibromides proceeds efficiently and selectively under very mild conditions to give the corresponding cycloadducts in good to excellent yields. The combination of manganese power with DMSO additive is crucial for the successful implementation of the present cycloaddition. Notably, the standard OPV acceptors, such as PCBMs, have been obtained in extraordinarily high yields, which cannot be achieved under the previously reported methods.
Highlights
Discovery of an efficient, practical, and flexible synthetic method to produce various important electron acceptors for low-cost organic photovoltaics (OPVs) is highly desirable
We have reported that the CoCl2dppf catalyst combined with a Mn reductant in o-dichlorobenzene (ODCB) promoted the monocycloaddition of C60 with active dibromides efficiently at room temperature to form the fullerene monocycloadducts in a high selectivity[30]
It was noted that the efforts to synthesize the biscycloadducts under the Co-catalyzed standard conditions even using an excess amount of dibromides were failed
Summary
Practical, and flexible synthetic method to produce various important electron acceptors for low-cost organic photovoltaics (OPVs) is highly desirable. Development of an innovative, practical synthetic method for those important fullerene acceptors under mild conditions with high production yields is highly desirable. Various fullerene functionalizations for synthesis of monosubstituted hydrofullerenes, monocycloadducts, single-bonded fullerene dimers, 1,4-disubstituted fullerenes have been developed in the presence of transition metal catalysts or oxidant via the formation of the fullerene monoradical as an active species[37]. These results led us to challenge the innovative, flexible synthetic method for those most common fullerene acceptors in very high yields
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