[2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior

The electronic coupling as well as the attenuation factor (β), which depends primarily on the nature of the molecular bridge and is used as a benchmark to test the molecular wire behavior, have been determined in a systematic study carried out on a series of ZnP/C60 conjugates connected through a [2...

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Detalles Bibliográficos
Autores: Molina Ontoria, Agustín, Wielopolski, Mateusz, Gebhardt, Julian, Gouloumis, Andreas, Clark, Timothy, Guldi, Dirk M., Martín León, Nazario
Tipo de recurso: artículo
Fecha de publicación:2011
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/114302
Acceso en línea:https://hdl.handle.net/20.500.14352/114302
Access Level:acceso abierto
Palabra clave:547
Absorption
Conjugate acid-base pairs
Excited states
Fluorescence
Wires
Química orgánica (Química)
2306 Química Orgánica
id ES_d6d7b696baeab4a5f6b06fb02fcb5a10
oai_identifier_str oai:docta.ucm.es:20.500.14352/114302
network_acronym_str ES
network_name_str España
repository_id_str
spelling [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction BehaviorMolina Ontoria, AgustínWielopolski, MateuszGebhardt, JulianGouloumis, AndreasClark, TimothyGuldi, Dirk M.Martín León, Nazario547AbsorptionConjugate acid-base pairsExcited statesFluorescenceWiresQuímica orgánica (Química)2306 Química OrgánicaThe electronic coupling as well as the attenuation factor (β), which depends primarily on the nature of the molecular bridge and is used as a benchmark to test the molecular wire behavior, have been determined in a systematic study carried out on a series of ZnP/C60 conjugates connected through a [2,20]paracyclophaneoligophenylenevinylene (pCp-oPPV). The convergent synthesis involves a series of Horner-Emmons olefination reactions or double palladium-catalized Heck-type reactions. ZnP-pCp-C60 conjugates were finally obtained by the 1,3-dipolar cycloaddition reaction of the in situ-generated azomethyne ylide containing the ZnP-pCp moiety to the [60]fullerene using Prato conditions. Experimental (UV-vis, fluorescence, transient absorption spectroscopy, and solution electrochemistry) and theoretical studies revealed that the pCps act as molecular junctions. If hole transfer is assumed to be the dominant charge transfer (CT) mechanism, CT is facilitated in one direction (from C60 to ZnP via pCp) but disfavored in the other direction (from ZnP to C60 via pCp).AMERICAN CHEMICAL SOCIETYUniversidad Complutense de Madrid20112011-02-0720112011-02-07journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/114302reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1143022026-06-02T12:44:21Z
dc.title.none.fl_str_mv [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
title [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
spellingShingle [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
Molina Ontoria, Agustín
547
Absorption
Conjugate acid-base pairs
Excited states
Fluorescence
Wires
Química orgánica (Química)
2306 Química Orgánica
title_short [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
title_full [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
title_fullStr [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
title_full_unstemmed [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
title_sort [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
dc.creator.none.fl_str_mv Molina Ontoria, Agustín
Wielopolski, Mateusz
Gebhardt, Julian
Gouloumis, Andreas
Clark, Timothy
Guldi, Dirk M.
Martín León, Nazario
author Molina Ontoria, Agustín
author_facet Molina Ontoria, Agustín
Wielopolski, Mateusz
Gebhardt, Julian
Gouloumis, Andreas
Clark, Timothy
Guldi, Dirk M.
Martín León, Nazario
author_role author
author2 Wielopolski, Mateusz
Gebhardt, Julian
Gouloumis, Andreas
Clark, Timothy
Guldi, Dirk M.
Martín León, Nazario
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Absorption
Conjugate acid-base pairs
Excited states
Fluorescence
Wires
Química orgánica (Química)
2306 Química Orgánica
topic 547
Absorption
Conjugate acid-base pairs
Excited states
Fluorescence
Wires
Química orgánica (Química)
2306 Química Orgánica
description The electronic coupling as well as the attenuation factor (β), which depends primarily on the nature of the molecular bridge and is used as a benchmark to test the molecular wire behavior, have been determined in a systematic study carried out on a series of ZnP/C60 conjugates connected through a [2,20]paracyclophaneoligophenylenevinylene (pCp-oPPV). The convergent synthesis involves a series of Horner-Emmons olefination reactions or double palladium-catalized Heck-type reactions. ZnP-pCp-C60 conjugates were finally obtained by the 1,3-dipolar cycloaddition reaction of the in situ-generated azomethyne ylide containing the ZnP-pCp moiety to the [60]fullerene using Prato conditions. Experimental (UV-vis, fluorescence, transient absorption spectroscopy, and solution electrochemistry) and theoretical studies revealed that the pCps act as molecular junctions. If hole transfer is assumed to be the dominant charge transfer (CT) mechanism, CT is facilitated in one direction (from C60 to ZnP via pCp) but disfavored in the other direction (from ZnP to C60 via pCp).
publishDate 2011
dc.date.none.fl_str_mv 2011
2011-02-07
2011
2011-02-07
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/20.500.14352/114302
url https://hdl.handle.net/20.500.14352/114302
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
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
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
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv AMERICAN CHEMICAL SOCIETY
publisher.none.fl_str_mv AMERICAN CHEMICAL SOCIETY
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
_version_ 1869420919831658496
score 15,812429

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