Synthesis, Electrochemical and Photophysical Properties, and Electroluminescent Performance of the Octa‐ and Deca(aryl)[60]fullerene Derivatives

Abstract

Abstract Three multifunctionalized organo[60]fullerene derivatives, C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 5 Me 2 (cyclophenacene, 1 ), C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 5 Me 2 (fused corannulene, 2 ), and C 60 Ph 5 (C 6 H 4 ‐ t Bu‐4) 3 Me 2 (phenylene‐bridged fused corannulene, 3 ) are synthesized by the reaction of C 60 Ph 5 Me with 4‐ tert ‐butylphenylcopper reagent in the presence of pyridine, followed by treatment with MeI. Compounds 1 – 3 undergo reduction in the range from −1.8 to −2.5 V versus Fc/Fc + and exhibit photoluminescence behavior with fluorescent quantum yields of 18.5%, 2.5%, and 3.2% with fluorescent lifetimes of 67, 1.1, and 27 ns ( 1 – 3 , respectively). Organic electroluminescent diode devices using 1 – 3 are fabricated with π‐conjugated polymers and show external electroluminescent efficiencies of 0.04%, 0.07%, and 0.03% emitting yellow, green, and red light, respectively. The device containing all three compounds emits white light. This result indicates that the bulky addends in 1 – 3 can effectively isolate the π‐conjugated systems of the molecules in the solid state and retard the intermolecular excited‐state quenching process.