Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters

The synthesis of the [6]helicene-based luminophores 1 and 2 is reported. These chiral systems, endowed with cyano-stilbene fragments, form supramolecular polymers by the operation of intermolecular H-bonding interactions between the amides present in the peripheral side chains. The dissimilar disubs...

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Autores: López Gandul, Lucia, Rodríguez Riego, Rafael, Vanthuyne, Nicolas, Crassous, Jeanne, Sánchez Martín, Luis
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/109216
Acceso en línea:https://hdl.handle.net/20.500.14352/109216
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
2306 Química Orgánica
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spelling Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emittersLópez Gandul, LuciaRodríguez Riego, RafaelVanthuyne, NicolasCrassous, JeanneSánchez Martín, Luis547Química orgánica (Química)2306 Química OrgánicaThe synthesis of the [6]helicene-based luminophores 1 and 2 is reported. These chiral systems, endowed with cyano-stilbene fragments, form supramolecular polymers by the operation of intermolecular H-bonding interactions between the amides present in the peripheral side chains. The dissimilar disubstitution of 1 and 2 plays a crucial role in their self-assembling features. Thus, 1 does not show an efficient π-stacking of the central aromatic moiety. Instead, its self-assembling process results in a zig-zag arrangement of the monomeric units to form the aggregated species. On the other hand, 2 presents an efficient overlap of the aromatic backbones that affords a co-facial arrangement of the monomeric units. The solvent-dependent studies indicate that both [6]helicenes self-assemble following a cooperative supramolecular polymerization mechanism with a higher degree of cooperativity and stability for compound 2. The enantioenriched samples of both 1 and 2 display a rich dichroic pattern that changes when the supramolecular polymerization takes place. Furthermore, the presence of the cyano-stilbene moieties gives rise to an aggregation induced emission effect. The inherent chirality of both the monomeric and aggregated species of 1 and 2 provides the systems with CPL-emitting properties, presenting a remarkable overall CPL-efficiency, quantified by the BCPL parameter, that increases upon supramolecular polymerization.Royal Society of ChemistryUniversidad Complutense de Madrid20242024-01-0120242024-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/109216reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)InglésengMCIN%AEI Not available PID2020- 113512GB-I00MCIN%AEI Not available TED2021-130285B-I00MCIN%AEI Juan de la Cierva Incorporación IJC2020-042689-IXunta de Galicia http://dx.doi.org/10.13039/501100010801 Centro Singular de Investigación de Galicia acreditación 2019-2022 ED431G 2019%03open 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:20.500.14352/1092162026-06-02T12:44:21Z
dc.title.none.fl_str_mv Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
title Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
spellingShingle Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
López Gandul, Lucia
547
Química orgánica (Química)
2306 Química Orgánica
title_short Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
title_full Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
title_fullStr Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
title_full_unstemmed Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
title_sort Supramolecular polymerization of [6]helicene-based cyano-luminogens: on the overall efficiency of self-assembled circularly polarized emitters
dc.creator.none.fl_str_mv López Gandul, Lucia
Rodríguez Riego, Rafael
Vanthuyne, Nicolas
Crassous, Jeanne
Sánchez Martín, Luis
author López Gandul, Lucia
author_facet López Gandul, Lucia
Rodríguez Riego, Rafael
Vanthuyne, Nicolas
Crassous, Jeanne
Sánchez Martín, Luis
author_role author
author2 Rodríguez Riego, Rafael
Vanthuyne, Nicolas
Crassous, Jeanne
Sánchez Martín, Luis
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
2306 Química Orgánica
topic 547
Química orgánica (Química)
2306 Química Orgánica
description The synthesis of the [6]helicene-based luminophores 1 and 2 is reported. These chiral systems, endowed with cyano-stilbene fragments, form supramolecular polymers by the operation of intermolecular H-bonding interactions between the amides present in the peripheral side chains. The dissimilar disubstitution of 1 and 2 plays a crucial role in their self-assembling features. Thus, 1 does not show an efficient π-stacking of the central aromatic moiety. Instead, its self-assembling process results in a zig-zag arrangement of the monomeric units to form the aggregated species. On the other hand, 2 presents an efficient overlap of the aromatic backbones that affords a co-facial arrangement of the monomeric units. The solvent-dependent studies indicate that both [6]helicenes self-assemble following a cooperative supramolecular polymerization mechanism with a higher degree of cooperativity and stability for compound 2. The enantioenriched samples of both 1 and 2 display a rich dichroic pattern that changes when the supramolecular polymerization takes place. Furthermore, the presence of the cyano-stilbene moieties gives rise to an aggregation induced emission effect. The inherent chirality of both the monomeric and aggregated species of 1 and 2 provides the systems with CPL-emitting properties, presenting a remarkable overall CPL-efficiency, quantified by the BCPL parameter, that increases upon supramolecular polymerization.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-01-01
2024
2024-01-01
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/20.500.14352/109216
url https://hdl.handle.net/20.500.14352/109216
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv MCIN%AEI Not available PID2020- 113512GB-I00
MCIN%AEI Not available TED2021-130285B-I00
MCIN%AEI Juan de la Cierva Incorporación IJC2020-042689-I
Xunta de Galicia http://dx.doi.org/10.13039/501100010801 Centro Singular de Investigación de Galicia acreditación 2019-2022 ED431G 2019%03
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 15.811543

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