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    Site-selective synthesis of b-[70]PCBM-like fullerenes: efficient application in perovskite solar cells
    (Wiley-VCH Verlag, 2019) Vidal, S.; Izquierdo, M.; Filippone, S.; Fernández, I.; Akın, Seçkin; Seo, J.-Y.; Zakeeruddin, S.M.
    We report on the site-selective synthesis of PCBM-like [70]fullerene site-isomers, where the elusive ?-site-isomers are, for the first time, the major product in a (cyclo)addition chemical reaction involving [70]fullerene. The reaction involves an straightforward cyclopropanation of [70]fullerene from sulfonium salts, affording a mixture of ? and ? site-isomers in good yields. Amazingly, the preference for the ?- or ?-site-isomer can be efficiently controlled by means of the solvent polarity! DFT theoretical calculations (DMF and toluene) nicely predict that, although the formation of the ?-adduct is, as expected, thermodynamically favored, the selectivity of the process is determined by the energy difference of the respective transition states. Furthermore, the employ of ? or/and ? site-isomers, as pure materials or as a mixture of them, used as templating agent, has been evaluated in perovskite solar cells. The positive influence of the [70]fullerenes by passivating the voids/pin-holes and/or deep slits, is reflected in highly efficient and stable bulk heterojunction perovskite solar cells, whose performance (around 20 %) is slightly but consistently depending on the isomeric fullerene composition. These experimental findings pave the way to investigate a new reactivity on C 70 and to explore the properties of the less-known ?-derivatives.