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

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

Vidal, Sara
•
Izquierdo, Marta
•
Filippone, Salvatore
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March 1, 2019
Chemistry-A European Journal

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.

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Type
research article
DOI
10.1002/chem.201806053
Web of Science ID

WOS:000460679500007

Author(s)
Vidal, Sara
•
Izquierdo, Marta
•
Filippone, Salvatore
•
Fernandez, Israel
•
Akin, Seckin
•
Seo, Ji-Youn  
•
Zakeeruddin, Shaik M.  
•
Graetzel, Michael  
•
Martin, Nazario
Date Issued

2019-03-01

Publisher

WILEY-V C H VERLAG GMBH

Published in
Chemistry-A European Journal
Volume

25

Issue

13

Start page

3224

End page

3228

Subjects

Chemistry, Multidisciplinary

•

Chemistry

•

cyclopropanation reaction

•

fullerenes

•

interface passivation

•

perovskite solar cells

•

site-selectivity

•

hole-transporting material

•

bisadduct regioisomers

•

highly efficient

•

performance

•

derivatives

•

solvent

•

scale

•

pcbm

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LPI  
Available on Infoscience
June 18, 2019
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/157636
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