Synthesis and Characterization of Pentafluorosulfanyl-Functionalized Fullerenes
Si-Yan Qing, Nicholas J. DeWeerd, Andrej V. Matsnev, Steven H. Strauss, Joseph S. Thrasher, Olga V. Boltalina
Index: 10.1016/j.jfluchem.2018.04.004
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Abstract
Fullerene C60 was reacted with SF5CF2CF2I and SF5CF2I 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 SF5CF2CF2I reagent produced three types of products, cycloadducts C60(c-C2F4)n, pentafluorosulfanyl products C60(CF2CF2SF5)m, and the mixed derivatives C60(C2F4)n(CF2CF2SF5)m. The optimization of the reaction conditions resulted in improved selectivity for the bis-adduct 1,7-C60(CF2CF2SF5)2, which was isolated and spectroscopically characterized. In the case of reactions between C60 and SF5CF2I, the unexpected formation of a mixture of derivatives with the general formula C60(CF3)n(CF2SF5)m was observed.