Synthesis and characterization of pentafluorosulfanyl-functionalized fullerenes

Abstract Fullerene C 60 was reacted with SF 5 CF 2 CF 2 I and SF 5 CF 2 I in the presence of Cu powder at 140–180 °C resulting in the successful production of the first pentafluorosulfanyl-functionalized fullerenes. In contrast to perfluoroalkyl iodides, which typically form (poly)perfluoroalkylfullerenes upon heating, the SF 5 CF 2 CF 2 I reagent produced three types of products, cycloadducts C 60 ( c -C 2 F 4 ) n , pentafluorosulfanyl products C 60 (CF 2 CF 2 SF 5 ) m , and the mixed derivatives C 60 (C 2 F 4 ) n (CF 2 CF 2 SF 5 ) m . The optimization of the reaction conditions resulted in improved selectivity for the bis -adduct 1,7-C 60 (CF 2 CF 2 SF 5 ) 2 , which was isolated and spectroscopically characterized. In the case of reactions between C 60 and SF 5 CF 2 I, the unexpected formation of a mixture of derivatives with the general formula C 60 (CF 3 ) n (CF 2 SF 5 ) m was observed.