Potassium salt promoted regioselective three-component coupling synthesis of 1,4-asymmetrical [60]fullerene bisadducts with superior electron transport properties.

Abstract

An efficient one-pot three-component domino coupling reaction of phenols, C60, and bromoalkanes was developed, resulting in the highly regioselective synthesis of 1,4-asymmetrical C60 bisadducts. The reaction utilizes KOtBu as a promoter and likely proceeds by an oxyanion/carbanion rearrangement/nucleophilic addition cascade. This new methodology is particularly effective for the synthesis of 1,4-asymmetrical C60 electron transport materials. Its utility is demonstrated by the synthesis of a new efficient 1,4-C60 ETM, which possesses better performance, easier synthesis, and a lower cost compared with the commercially available PCBM.