Successive Diels–Alder Cycloadditions of Cyclopentadiene to [10]CPP⊃C60: A Computational Study
dc.contributor.author
dc.date.accessioned
2022-06-01T07:01:40Z
dc.date.available
2022-06-01T07:01:40Z
dc.date.issued
2022-03-23
dc.identifier.issn
0022-3263
dc.identifier.uri
dc.description.abstract
Fullerenes have potential applications in many fields. To reach their full potential, fullerenes have to be functionalized. One of the most common reactions used to functionalize fullerenes is the Diels–Alder cycloaddition. In this case, it is important to control the regioselectivity of the cycloaddition during the formation of higher adducts. In C60, successive Diels–Alder cycloadditions lead to the Th-symmetric hexakisadduct. In this work, we explore computationally using density functional theory (DFT) how the presence of a [10]cycloparaphenylene ring encapsulating C60 ([10]CPP⊃C60) affects the regioselectivity of multiple additions to C60. Our results show that the presence of the [10]CPP ring changes the preferred sites of cycloaddition compared to free C60 and leads to the formation of the tetrakisadduct. Somewhat surprisingly, our calculations predict formation of this particular tetrakisadduct to be more favored in [10]CPP⊃C60 than in free C60
dc.description.sponsorship
A.P. is a Serra Hunter Fellow and ICREA Academia Prize ́
2019. A.P., S.S,and M.S. thank the Spanish MINECO for
projects PGC2018-097722-B-I00 and PID2020-113711GB-I00
and the Generalitat de Catalunya for project 2017SGR39. The
work was performed under the Project HPC-EUROPA3
(HPC17870HV), with the support of the EC Research
Innovation Action under the H2020 Programme. G.P.
gratefully acknowledges the support of Institut de Química
Computacional i Catalisis (IQCC) and the computer resources ̀
and technical support provided by the Barcelona Supercomputing Center (CNS-BSC) and the Irish Centre for HighEnd Computing (ICHEC). Open Access funding provided
thanks to the CRUE-CSIC agreement with ACS
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
PGC2018-097722-B-I00
PID2020-113711GB-I00
dc.relation.isformatof
Reproducció digital del document publicat a: https://doi.org/10.1021/acs.joc.1c03116
dc.relation.ispartof
Journal of Organic Chemistry, 2022, vol. 87, núm. 8, p. 5149–5157
dc.relation.ispartofseries
Articles publicats (D-Q)
dc.rights
Attribution 4.0 International
dc.rights.uri
dc.subject
dc.title
Successive Diels–Alder Cycloadditions of Cyclopentadiene to [10]CPP⊃C60: A Computational Study
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.relation.projectID
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-097722-B-I00/ES/REDESCUBRIMIENTO IN SILICO DE MECANISMOS ASISTIDOS DUALES DE LA CATALISIS MONOMETALICA: HACIA EL TRABAJO EN CONDICIONES SUAVES/
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-113711GB-I00/ES/DISEÑO Y SINTESIS DE FULLERENOS PARA LA CONSTRUCCION DE CELDAS SOLARES HIBRIDAS DE PEROVSKITA Y FULERENOS D ALTO RENDIMIENTO. UN ENFOQUE EXPERIMENTAL Y COMPUTACIONAL SINERGICO/
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
035323
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
dc.relation.FundingProgramme
dc.relation.ProjectAcronym
dc.identifier.eissn
1520-6904