Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles

Autores
Silva, Oscar Fernando; Correa, Nestor Mariano; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Fernández, Mariana Adela
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this contribution we show the effect of the surfactant polar head and the external solvent on the incorporation of different cyclodextrins (CDs) {α-CD, β-CD, γ-CD, decenylsuccinyl-β-CD (Mod-β-CD), and hydroxypropyl-β-CD (hp-β-CD)} in different reverse micelles (RMs) {benzene/sodium 1,4-bis(2-ethylhexyl) sulfosuccinate(AOT)/water, and benzene/benzyl-n-hexadecyldimethylammonium chloride (BHDC)/water} and compare them with previous results obtained in n-heptane/AOT/water RMs. To investigate the different systems, we have used UV–vis spectrophotometry, induced circular dichroism spectroscopy (ICD), and the achiral molecular probe methyl orange (MO). The results show dramatic differences changing the external solvent and the surfactant, which are explained by considering the differences in the RMs interface composition, the water–surfactant interaction, and the CDs’ location in the different media investigated. None of the CDs were incorporated into the benzene/AOT/water RMs at any [H2O]/[surfactant] ratio studied (W0) whereas it was previously shown that Mod-β-CD and hp-β-CD could be included in n-heptane/AOT/water RMs. However, all of the CDs are incorporated in benzene/BHDC/water RMs at W0 > 10 and hp-β-CD is dissolved even at W0 = 0. Different from what was found in n-heptane/AOT RMs, in BHDC RMs MO showed ICD signals with two different CDs: Mod-β-CD and hp-β-CD. The results are explained by considering the known difference in the interfacial water structure for AOT and BHDC RMs and the electron-rich region on the secondary hydroxyl (wider side of the CDs), which helps to solubilize all CDs in BHDC. This study shows that chiral cyclodextrin could be available for a guest in an organic medium such as the RMs. Therefore we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
Fil: Silva, Oscar Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; Argentina
Fil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto; Argentina
Fil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Fernández, Mariana Adela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Cycilodextrins
Reverse Micelle
Chiral Complex
Dichroism Circular Induced
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/31570
Acceder
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spelling Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse MicellesSilva, Oscar FernandoCorrea, Nestor MarianoChessa, Juana JosefaHoyos, Maria Rita MicaelaFernández, Mariana AdelaCycilodextrinsReverse MicelleChiral ComplexDichroism Circular Inducedhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this contribution we show the effect of the surfactant polar head and the external solvent on the incorporation of different cyclodextrins (CDs) {α-CD, β-CD, γ-CD, decenylsuccinyl-β-CD (Mod-β-CD), and hydroxypropyl-β-CD (hp-β-CD)} in different reverse micelles (RMs) {benzene/sodium 1,4-bis(2-ethylhexyl) sulfosuccinate(AOT)/water, and benzene/benzyl-n-hexadecyldimethylammonium chloride (BHDC)/water} and compare them with previous results obtained in n-heptane/AOT/water RMs. To investigate the different systems, we have used UV–vis spectrophotometry, induced circular dichroism spectroscopy (ICD), and the achiral molecular probe methyl orange (MO). The results show dramatic differences changing the external solvent and the surfactant, which are explained by considering the differences in the RMs interface composition, the water–surfactant interaction, and the CDs’ location in the different media investigated. None of the CDs were incorporated into the benzene/AOT/water RMs at any [H2O]/[surfactant] ratio studied (W0) whereas it was previously shown that Mod-β-CD and hp-β-CD could be included in n-heptane/AOT/water RMs. However, all of the CDs are incorporated in benzene/BHDC/water RMs at W0 > 10 and hp-β-CD is dissolved even at W0 = 0. Different from what was found in n-heptane/AOT RMs, in BHDC RMs MO showed ICD signals with two different CDs: Mod-β-CD and hp-β-CD. The results are explained by considering the known difference in the interfacial water structure for AOT and BHDC RMs and the electron-rich region on the secondary hydroxyl (wider side of the CDs), which helps to solubilize all CDs in BHDC. This study shows that chiral cyclodextrin could be available for a guest in an organic medium such as the RMs. Therefore we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.Fil: Silva, Oscar Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; ArgentinaFil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto; ArgentinaFil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Fernández, Mariana Adela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaAmerican Chemical Society2014-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31570Silva, Oscar Fernando; Correa, Nestor Mariano; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Fernández, Mariana Adela; Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles; American Chemical Society; Langmuir; 30; 12; 3-2014; 3354-33620743-7463CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/la404584qinfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/la404584qinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:21:40Zoai:ri.conicet.gov.ar:11336/31570instacron: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:34982025-10-15 14:21:40.925CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
title Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
spellingShingle Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
Silva, Oscar Fernando
Cycilodextrins
Reverse Micelle
Chiral Complex
Dichroism Circular Induced
title_short Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
title_full Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
title_fullStr Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
title_full_unstemmed Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
title_sort Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles
dc.creator.none.fl_str_mv Silva, Oscar Fernando
Correa, Nestor Mariano
Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Fernández, Mariana Adela
author Silva, Oscar Fernando
author_facet Silva, Oscar Fernando
Correa, Nestor Mariano
Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Fernández, Mariana Adela
author_role author
author2 Correa, Nestor Mariano
Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Fernández, Mariana Adela
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cycilodextrins
Reverse Micelle
Chiral Complex
Dichroism Circular Induced
topic Cycilodextrins
Reverse Micelle
Chiral Complex
Dichroism Circular Induced
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this contribution we show the effect of the surfactant polar head and the external solvent on the incorporation of different cyclodextrins (CDs) {α-CD, β-CD, γ-CD, decenylsuccinyl-β-CD (Mod-β-CD), and hydroxypropyl-β-CD (hp-β-CD)} in different reverse micelles (RMs) {benzene/sodium 1,4-bis(2-ethylhexyl) sulfosuccinate(AOT)/water, and benzene/benzyl-n-hexadecyldimethylammonium chloride (BHDC)/water} and compare them with previous results obtained in n-heptane/AOT/water RMs. To investigate the different systems, we have used UV–vis spectrophotometry, induced circular dichroism spectroscopy (ICD), and the achiral molecular probe methyl orange (MO). The results show dramatic differences changing the external solvent and the surfactant, which are explained by considering the differences in the RMs interface composition, the water–surfactant interaction, and the CDs’ location in the different media investigated. None of the CDs were incorporated into the benzene/AOT/water RMs at any [H2O]/[surfactant] ratio studied (W0) whereas it was previously shown that Mod-β-CD and hp-β-CD could be included in n-heptane/AOT/water RMs. However, all of the CDs are incorporated in benzene/BHDC/water RMs at W0 > 10 and hp-β-CD is dissolved even at W0 = 0. Different from what was found in n-heptane/AOT RMs, in BHDC RMs MO showed ICD signals with two different CDs: Mod-β-CD and hp-β-CD. The results are explained by considering the known difference in the interfacial water structure for AOT and BHDC RMs and the electron-rich region on the secondary hydroxyl (wider side of the CDs), which helps to solubilize all CDs in BHDC. This study shows that chiral cyclodextrin could be available for a guest in an organic medium such as the RMs. Therefore we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
Fil: Silva, Oscar Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; Argentina
Fil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto; Argentina
Fil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Fernández, Mariana Adela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description In this contribution we show the effect of the surfactant polar head and the external solvent on the incorporation of different cyclodextrins (CDs) {α-CD, β-CD, γ-CD, decenylsuccinyl-β-CD (Mod-β-CD), and hydroxypropyl-β-CD (hp-β-CD)} in different reverse micelles (RMs) {benzene/sodium 1,4-bis(2-ethylhexyl) sulfosuccinate(AOT)/water, and benzene/benzyl-n-hexadecyldimethylammonium chloride (BHDC)/water} and compare them with previous results obtained in n-heptane/AOT/water RMs. To investigate the different systems, we have used UV–vis spectrophotometry, induced circular dichroism spectroscopy (ICD), and the achiral molecular probe methyl orange (MO). The results show dramatic differences changing the external solvent and the surfactant, which are explained by considering the differences in the RMs interface composition, the water–surfactant interaction, and the CDs’ location in the different media investigated. None of the CDs were incorporated into the benzene/AOT/water RMs at any [H2O]/[surfactant] ratio studied (W0) whereas it was previously shown that Mod-β-CD and hp-β-CD could be included in n-heptane/AOT/water RMs. However, all of the CDs are incorporated in benzene/BHDC/water RMs at W0 > 10 and hp-β-CD is dissolved even at W0 = 0. Different from what was found in n-heptane/AOT RMs, in BHDC RMs MO showed ICD signals with two different CDs: Mod-β-CD and hp-β-CD. The results are explained by considering the known difference in the interfacial water structure for AOT and BHDC RMs and the electron-rich region on the secondary hydroxyl (wider side of the CDs), which helps to solubilize all CDs in BHDC. This study shows that chiral cyclodextrin could be available for a guest in an organic medium such as the RMs. Therefore we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
publishDate 2014
dc.date.none.fl_str_mv 2014-03
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/11336/31570
Silva, Oscar Fernando; Correa, Nestor Mariano; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Fernández, Mariana Adela; Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles; American Chemical Society; Langmuir; 30; 12; 3-2014; 3354-3362
0743-7463
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31570
identifier_str_mv Silva, Oscar Fernando; Correa, Nestor Mariano; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Fernández, Mariana Adela; Supramolecular Assemblies Obtained by Mixing Different Cyclodextrins and AOT or BHDC Reverse Micelles; American Chemical Society; Langmuir; 30; 12; 3-2014; 3354-3362
0743-7463
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/la404584q
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/la404584q
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
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: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
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