Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules

Autores
Nador, Fabiana Gabriela; Wnuk, Karolina; Roscini, Claudio; Solorzano, Ruben; Faraudo, Jordi; Ruiz Molina, Daniel; Novio, Fernando
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis and structuration of a novel low‐molecular‐weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene‐based hydrophobic head favors solvent‐tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril‐like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self‐assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle‐like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent‐driven supramolecular interactions.
Fil: Nador, Fabiana Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Consejo Superior de Investigaciones Científicas; España
Fil: Wnuk, Karolina. Consejo Superior de Investigaciones Científicas; España
Fil: Roscini, Claudio. Consejo Superior de Investigaciones Científicas; España
Fil: Solorzano, Ruben. Consejo Superior de Investigaciones Científicas; España. Universitat Autònoma de Barcelona; España
Fil: Faraudo, Jordi. Consejo Superior de Investigaciones Científicas; España
Fil: Ruiz Molina, Daniel. Consejo Superior de Investigaciones Científicas; España
Fil: Novio, Fernando. Universitat Autònoma de Barcelona; España. Consejo Superior de Investigaciones Científicas; España
Materia
CATECHOL
SELF-ASSEMBLY
VESICLES
SUPRAMOLECULAR CHEMISTRY
FLUORESCENCE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/91348
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/91348
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic MoleculesNador, Fabiana GabrielaWnuk, KarolinaRoscini, ClaudioSolorzano, RubenFaraudo, JordiRuiz Molina, DanielNovio, FernandoCATECHOLSELF-ASSEMBLYVESICLESSUPRAMOLECULAR CHEMISTRYFLUORESCENCEhttps://purl.org/becyt/ford/2.10https://purl.org/becyt/ford/2The synthesis and structuration of a novel low‐molecular‐weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene‐based hydrophobic head favors solvent‐tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril‐like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self‐assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle‐like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent‐driven supramolecular interactions.Fil: Nador, Fabiana Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Consejo Superior de Investigaciones Científicas; EspañaFil: Wnuk, Karolina. Consejo Superior de Investigaciones Científicas; EspañaFil: Roscini, Claudio. Consejo Superior de Investigaciones Científicas; EspañaFil: Solorzano, Ruben. Consejo Superior de Investigaciones Científicas; España. Universitat Autònoma de Barcelona; EspañaFil: Faraudo, Jordi. Consejo Superior de Investigaciones Científicas; EspañaFil: Ruiz Molina, Daniel. Consejo Superior de Investigaciones Científicas; EspañaFil: Novio, Fernando. Universitat Autònoma de Barcelona; España. Consejo Superior de Investigaciones Científicas; EspañaWiley VCH Verlag2018-06-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/91348Nador, Fabiana Gabriela; Wnuk, Karolina; Roscini, Claudio; Solorzano, Ruben; Faraudo, Jordi; et al.; Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules; Wiley VCH Verlag; Chemistry- A European Journal; 24; 55; 13-6-2018; 14724-147320947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201802249info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201802249info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:03:41Zoai:ri.conicet.gov.ar:11336/91348instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 10:03:41.845CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
title Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
spellingShingle Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
Nador, Fabiana Gabriela
CATECHOL
SELF-ASSEMBLY
VESICLES
SUPRAMOLECULAR CHEMISTRY
FLUORESCENCE
title_short Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
title_full Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
title_fullStr Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
title_full_unstemmed Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
title_sort Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules
dc.creator.none.fl_str_mv Nador, Fabiana Gabriela
Wnuk, Karolina
Roscini, Claudio
Solorzano, Ruben
Faraudo, Jordi
Ruiz Molina, Daniel
Novio, Fernando
author Nador, Fabiana Gabriela
author_facet Nador, Fabiana Gabriela
Wnuk, Karolina
Roscini, Claudio
Solorzano, Ruben
Faraudo, Jordi
Ruiz Molina, Daniel
Novio, Fernando
author_role author
author2 Wnuk, Karolina
Roscini, Claudio
Solorzano, Ruben
Faraudo, Jordi
Ruiz Molina, Daniel
Novio, Fernando
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv CATECHOL
SELF-ASSEMBLY
VESICLES
SUPRAMOLECULAR CHEMISTRY
FLUORESCENCE
topic CATECHOL
SELF-ASSEMBLY
VESICLES
SUPRAMOLECULAR CHEMISTRY
FLUORESCENCE
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.10
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The synthesis and structuration of a novel low‐molecular‐weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene‐based hydrophobic head favors solvent‐tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril‐like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self‐assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle‐like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent‐driven supramolecular interactions.
Fil: Nador, Fabiana Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Consejo Superior de Investigaciones Científicas; España
Fil: Wnuk, Karolina. Consejo Superior de Investigaciones Científicas; España
Fil: Roscini, Claudio. Consejo Superior de Investigaciones Científicas; España
Fil: Solorzano, Ruben. Consejo Superior de Investigaciones Científicas; España. Universitat Autònoma de Barcelona; España
Fil: Faraudo, Jordi. Consejo Superior de Investigaciones Científicas; España
Fil: Ruiz Molina, Daniel. Consejo Superior de Investigaciones Científicas; España
Fil: Novio, Fernando. Universitat Autònoma de Barcelona; España. Consejo Superior de Investigaciones Científicas; España
description The synthesis and structuration of a novel low‐molecular‐weight amphiphilic catechol compound is reported. The combination of a hydrophilic tail containing a catechol unit and a pyrene‐based hydrophobic head favors solvent‐tuned supramolecular assembly. Formation of hollow nanocapsules/vesicles occurs in concentrated solutions of polar protic and nonprotic organic solvents, whereas a fibril‐like aggregation process is favored in water, even at low concentrations. The emission properties of the pyrene moiety allow monitoring of the self‐assembly process, which could be confirmed by optical and electronic microscopy. In organic solvents and at low concentrations, this compound remains in its nonassembled monomeric form. As the concentration increases, the aggregation containing preassociated pyrene moieties becomes more evident up to a critical micellar concentration, at which vesicle‐like structures are formed. In contrast, nanosized twist beltlike fibers are observed in water, even at low concentrations, whereas microplate structures appear at high concentrations. The interactions between molecules in different solvents were studied by using molecular dynamics simulations, which have confirmed different solvent‐driven supramolecular interactions.
publishDate 2018
dc.date.none.fl_str_mv 2018-06-13
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/91348
Nador, Fabiana Gabriela; Wnuk, Karolina; Roscini, Claudio; Solorzano, Ruben; Faraudo, Jordi; et al.; Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules; Wiley VCH Verlag; Chemistry- A European Journal; 24; 55; 13-6-2018; 14724-14732
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/91348
identifier_str_mv Nador, Fabiana Gabriela; Wnuk, Karolina; Roscini, Claudio; Solorzano, Ruben; Faraudo, Jordi; et al.; Solvent-Tuned Supramolecular Assembly of Fluorescent Catechol/Pyrene Amphiphilic Molecules; Wiley VCH Verlag; Chemistry- A European Journal; 24; 55; 13-6-2018; 14724-14732
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201802249
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201802249
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842269814464184320
score 13.11938

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