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 KO^tBu 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.