Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production

The regioselective functionalization of fullerenes holds significant promise for applications in the field of medicinal chemistry, material science and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2+2+2] cycloaddition reaction between diynes and C70...

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Autores: Castanyer, Cristina, Pla i Quintana, Anna, Roglans i Ribas, Anna, Artigas Ruf, Albert, Solà i Puig, Miquel
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/24803
Acceso en línea:http://hdl.handle.net/10256/24803
Access Level:acceso abierto
Palabra clave:Ciclització (Química)
Ful·lerens
Rodi
Ring formation (Chemistry)
Fullerenes
Rhodium
Reaccions químiques regioselectives
Funcional de densitat, Teoria del
Density functionals
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spelling Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 productionCastanyer, CristinaPla i Quintana, AnnaRoglans i Ribas, AnnaArtigas Ruf, AlbertSolà i Puig, MiquelCiclització (Química)Ful·lerensRodiRing formation (Chemistry)FullerenesRhodiumReaccions químiques regioselectivesFuncional de densitat, Teoria delDensity functionalsThe regioselective functionalization of fullerenes holds significant promise for applications in the field of medicinal chemistry, material science and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2+2+2] cycloaddition reaction between diynes and C70 as a novel procedure for generating C70 bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches. In addition, the photooxidation of one of the C=C double bonds in the synthesised bis(fulleroids) afford open-cage C70 derivatives having a 12-membered ring openingWe are grateful for the financial support from the Ministerio de Ciencia e Innovación and EU (Project PID2020-113711GB-I00 MCIN/AEI/10.13039/50110001103, FPI predoctoral grant to C.C. and Margarita Salas grant (NextGenerationEU) to A.A.) and the Generalitat de Catalunya (Project 2021-SGR-623)Beilstein-InstitutAgencia Estatal de Investigación2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewed8 p.application/pdfhttp://hdl.handle.net/10256/24803http://hdl.handle.net/10256/24803Beilstein Journal of Organic Chemistry, 2024, vol. 20, p. 272-279Articles publicats (D-Q)Castanyer, Cristina Pla i Quintana, Anna Roglans i Ribas, Anna Artigas Ruf, Albert Solà i Puig, Miquel 2024 Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production Beilstein Journal of Organic Chemistry 20 272 279reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.20.28info:eu-repo/semantics/altIdentifier/eissn/1860-5397PID2020-113711GB-I00info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-113711GB-I00Attribution 4.0 International (CC BY 4.0)https://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/248032026-05-29T05:05:01Z
dc.title.none.fl_str_mv Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
title Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
spellingShingle Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
Castanyer, Cristina
Ciclització (Química)
Ful·lerens
Rodi
Ring formation (Chemistry)
Fullerenes
Rhodium
Reaccions químiques regioselectives
Funcional de densitat, Teoria del
Density functionals
title_short Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
title_full Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
title_fullStr Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
title_full_unstemmed Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
title_sort Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
dc.creator.none.fl_str_mv Castanyer, Cristina
Pla i Quintana, Anna
Roglans i Ribas, Anna
Artigas Ruf, Albert
Solà i Puig, Miquel
author Castanyer, Cristina
author_facet Castanyer, Cristina
Pla i Quintana, Anna
Roglans i Ribas, Anna
Artigas Ruf, Albert
Solà i Puig, Miquel
author_role author
author2 Pla i Quintana, Anna
Roglans i Ribas, Anna
Artigas Ruf, Albert
Solà i Puig, Miquel
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación
dc.subject.none.fl_str_mv Ciclització (Química)
Ful·lerens
Rodi
Ring formation (Chemistry)
Fullerenes
Rhodium
Reaccions químiques regioselectives
Funcional de densitat, Teoria del
Density functionals
topic Ciclització (Química)
Ful·lerens
Rodi
Ring formation (Chemistry)
Fullerenes
Rhodium
Reaccions químiques regioselectives
Funcional de densitat, Teoria del
Density functionals
description The regioselective functionalization of fullerenes holds significant promise for applications in the field of medicinal chemistry, material science and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2+2+2] cycloaddition reaction between diynes and C70 as a novel procedure for generating C70 bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches. In addition, the photooxidation of one of the C=C double bonds in the synthesised bis(fulleroids) afford open-cage C70 derivatives having a 12-membered ring opening
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/24803
http://hdl.handle.net/10256/24803
url http://hdl.handle.net/10256/24803
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.20.28
info:eu-repo/semantics/altIdentifier/eissn/1860-5397
PID2020-113711GB-I00
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-113711GB-I00
dc.rights.none.fl_str_mv Attribution 4.0 International (CC BY 4.0)
https://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 4.0 International (CC BY 4.0)
https://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 8 p.
application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
dc.source.none.fl_str_mv Beilstein Journal of Organic Chemistry, 2024, vol. 20, p. 272-279
Articles publicats (D-Q)
Castanyer, Cristina Pla i Quintana, Anna Roglans i Ribas, Anna Artigas Ruf, Albert Solà i Puig, Miquel 2024 Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production Beilstein Journal of Organic Chemistry 20 272 279
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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