Site-selective Synthesis of -[70]PCBM-like Fullerenes: Efficient Application in Perovskite Solar Cells

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.


Published in:
Chemistry-A European Journal, 25, 13, 3224-3228
Year:
Mar 01 2019
Publisher:
Weinheim, WILEY-V C H VERLAG GMBH
ISSN:
0947-6539
1521-3765
Keywords:
Laboratories:




 Record created 2019-06-18, last modified 2019-06-25


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