Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell

We report on the site-selective synthesis of PCBM-like [70]fullerene site-isomers, where the elusive β-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 fr...

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Autores: Vidal, Sara, Filippone, Salvatore, Izquierdo, Marta, Fernández López, Israel, Akin, Seckin, Seo, Ji-Youn, Zakeeruddin, Shaik M., Grätzel, Michael, Martín León, Nazario
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/130940
Acceso en línea:https://hdl.handle.net/20.500.14352/130940
Access Level:acceso abierto
Palabra clave:547
Cyclopropanation reaction
Fullerenes
Interface passivation
Perovskite solar cells
Site-selectivity
Ciencias
23 Química
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oai_identifier_str oai:docta.ucm.es:20.500.14352/130940
network_acronym_str ES
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repository_id_str
spelling Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar CellVidal, SaraFilippone, SalvatoreIzquierdo, MartaFernández López, IsraelAkin, SeckinSeo, Ji-YounZakeeruddin, Shaik M.Grätzel, MichaelMartín León, Nazario547Cyclopropanation reactionFullerenesInterface passivationPerovskite solar cellsSite-selectivityCiencias23 QuímicaWe report on the site-selective synthesis of PCBM-like [70]fullerene site-isomers, where the elusive β-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 α and β site-isomers in good yields. Amazingly, the preference for the α- or β-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 α-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 α or/and β 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 C70 and to explore the properties of the less-known β-derivativesWileyUniversidad Complutense de Madrid20192019-01-1820192019-01-18journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/130940reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1309402026-06-02T12:44:21Z
dc.title.none.fl_str_mv Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
title Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
spellingShingle Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
Vidal, Sara
547
Cyclopropanation reaction
Fullerenes
Interface passivation
Perovskite solar cells
Site-selectivity
Ciencias
23 Química
title_short Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
title_full Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
title_fullStr Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
title_full_unstemmed Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
title_sort Site-selective Synthesis of b-[70]PCBM-like Fullerenes: EfficientApplication in Perovskite Solar Cell
dc.creator.none.fl_str_mv Vidal, Sara
Filippone, Salvatore
Izquierdo, Marta
Fernández López, Israel
Akin, Seckin
Seo, Ji-Youn
Zakeeruddin, Shaik M.
Grätzel, Michael
Martín León, Nazario
author Vidal, Sara
author_facet Vidal, Sara
Filippone, Salvatore
Izquierdo, Marta
Fernández López, Israel
Akin, Seckin
Seo, Ji-Youn
Zakeeruddin, Shaik M.
Grätzel, Michael
Martín León, Nazario
author_role author
author2 Filippone, Salvatore
Izquierdo, Marta
Fernández López, Israel
Akin, Seckin
Seo, Ji-Youn
Zakeeruddin, Shaik M.
Grätzel, Michael
Martín León, Nazario
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Cyclopropanation reaction
Fullerenes
Interface passivation
Perovskite solar cells
Site-selectivity
Ciencias
23 Química
topic 547
Cyclopropanation reaction
Fullerenes
Interface passivation
Perovskite solar cells
Site-selectivity
Ciencias
23 Química
description We report on the site-selective synthesis of PCBM-like [70]fullerene site-isomers, where the elusive β-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 α and β site-isomers in good yields. Amazingly, the preference for the α- or β-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 α-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 α or/and β 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 C70 and to explore the properties of the less-known β-derivatives
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-01-18
2019
2019-01-18
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/130940
url https://hdl.handle.net/20.500.14352/130940
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812455

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