Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids

Autores
Alexander, Francesca M.; Fonrouge Kotik, Sergio Federico; Borioni, José Luis; del Popolo, Mario Gabriel; Horton, Peter N.; Coles, Simon J.; Hutchings, Benjamin P.; Crawford, Deborah E.; James, Stuart L.
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Porous Liquids (PLs) are a new class of material that possess both fluidity and permanent porosity. As such they can act as enhanced, selective solvents and may ultimately find applications which are not possible for porous solids, such as continuous flow separation processes. Type II PLs consist of empty molecular hosts dissolved in size-excluded solvents and to date have mainly been based on hosts that have limited chemical and thermal stability. Here we identify Noria, a rigid cyclic oligomer as a new host for the synthesis of more robust Type II PLs. Although the structure of Noria is well-documented, we find that literature has overlooked the true composition of bulk Noria samples. We find that bulk samples typically consist of Noria (ca.40%), a Noria isomer, specifically a resorcinarene trimer, “R3” (ca.30%) and other unidentified oligomers (ca.30%). Noria has been characterised crystallographically as a diethyl ether solvate and its1H NMR spectrum fully assigned for the first time. The previously postulated but unreported R3 has also been characterised crystallographically as a dimethyl sulfoxide solvate, which confirms its alternative connectivity to Noria. Noria and R3 have low solubility which precludes their use in Type II PLs, however, the partially ethylated derivative Noria-OEt dissolves in the size-excluded solvent 15-crown-5 to give a new Type II PL. This PL exhibits enhanced uptake of methane (CH4) gas supporting the presence of empty pores in the liquid. Detailed molecular dynamics simulations support the existence of pores in the liquid and show that occupation of the pores by CH4is favoured. Overall, this work revises the general accepted composition of bulk Noria samples and shows that Noria derivatives are appropriate for the synthesis of more robust Type II PLs.
Fil: Alexander, Francesca M.. The Queens University of Belfast; Irlanda
Fil: Fonrouge Kotik, Sergio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: Borioni, José Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: del Popolo, Mario Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: Horton, Peter N.. University of Southampton; Reino Unido
Fil: Coles, Simon J.. University of Southampton; Reino Unido
Fil: Hutchings, Benjamin P.. The Queens University of Belfast; Irlanda
Fil: Crawford, Deborah E.. University of Bradford; Reino Unido
Fil: James, Stuart L.. The Queens University of Belfast; Irlanda
Materia
POROUS LIQUIDS
NORIA
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/173844
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/173844
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquidsAlexander, Francesca M.Fonrouge Kotik, Sergio FedericoBorioni, José Luisdel Popolo, Mario GabrielHorton, Peter N.Coles, Simon J.Hutchings, Benjamin P.Crawford, Deborah E.James, Stuart L.POROUS LIQUIDSNORIAhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Porous Liquids (PLs) are a new class of material that possess both fluidity and permanent porosity. As such they can act as enhanced, selective solvents and may ultimately find applications which are not possible for porous solids, such as continuous flow separation processes. Type II PLs consist of empty molecular hosts dissolved in size-excluded solvents and to date have mainly been based on hosts that have limited chemical and thermal stability. Here we identify Noria, a rigid cyclic oligomer as a new host for the synthesis of more robust Type II PLs. Although the structure of Noria is well-documented, we find that literature has overlooked the true composition of bulk Noria samples. We find that bulk samples typically consist of Noria (ca.40%), a Noria isomer, specifically a resorcinarene trimer, “R3” (ca.30%) and other unidentified oligomers (ca.30%). Noria has been characterised crystallographically as a diethyl ether solvate and its1H NMR spectrum fully assigned for the first time. The previously postulated but unreported R3 has also been characterised crystallographically as a dimethyl sulfoxide solvate, which confirms its alternative connectivity to Noria. Noria and R3 have low solubility which precludes their use in Type II PLs, however, the partially ethylated derivative Noria-OEt dissolves in the size-excluded solvent 15-crown-5 to give a new Type II PL. This PL exhibits enhanced uptake of methane (CH4) gas supporting the presence of empty pores in the liquid. Detailed molecular dynamics simulations support the existence of pores in the liquid and show that occupation of the pores by CH4is favoured. Overall, this work revises the general accepted composition of bulk Noria samples and shows that Noria derivatives are appropriate for the synthesis of more robust Type II PLs.Fil: Alexander, Francesca M.. The Queens University of Belfast; IrlandaFil: Fonrouge Kotik, Sergio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; ArgentinaFil: Borioni, José Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; ArgentinaFil: del Popolo, Mario Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; ArgentinaFil: Horton, Peter N.. University of Southampton; Reino UnidoFil: Coles, Simon J.. University of Southampton; Reino UnidoFil: Hutchings, Benjamin P.. The Queens University of Belfast; IrlandaFil: Crawford, Deborah E.. University of Bradford; Reino UnidoFil: James, Stuart L.. The Queens University of Belfast; IrlandaRoyal Society of Chemistry2021-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/173844Alexander, Francesca M.; Fonrouge Kotik, Sergio Federico; Borioni, José Luis; del Popolo, Mario Gabriel; Horton, Peter N.; et al.; Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids; Royal Society of Chemistry; Chemical Science; 12; 42; 11-2021; 14230-142402041-65202041-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2021/SC/D1SC03367Kinfo:eu-repo/semantics/altIdentifier/doi/10.1039/d1sc03367kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:47:35Zoai:ri.conicet.gov.ar:11336/173844instacron: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 14:47:35.889CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
title Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
spellingShingle Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
Alexander, Francesca M.
POROUS LIQUIDS
NORIA
title_short Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
title_full Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
title_fullStr Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
title_full_unstemmed Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
title_sort Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids
dc.creator.none.fl_str_mv Alexander, Francesca M.
Fonrouge Kotik, Sergio Federico
Borioni, José Luis
del Popolo, Mario Gabriel
Horton, Peter N.
Coles, Simon J.
Hutchings, Benjamin P.
Crawford, Deborah E.
James, Stuart L.
author Alexander, Francesca M.
author_facet Alexander, Francesca M.
Fonrouge Kotik, Sergio Federico
Borioni, José Luis
del Popolo, Mario Gabriel
Horton, Peter N.
Coles, Simon J.
Hutchings, Benjamin P.
Crawford, Deborah E.
James, Stuart L.
author_role author
author2 Fonrouge Kotik, Sergio Federico
Borioni, José Luis
del Popolo, Mario Gabriel
Horton, Peter N.
Coles, Simon J.
Hutchings, Benjamin P.
Crawford, Deborah E.
James, Stuart L.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv POROUS LIQUIDS
NORIA
topic POROUS LIQUIDS
NORIA
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Porous Liquids (PLs) are a new class of material that possess both fluidity and permanent porosity. As such they can act as enhanced, selective solvents and may ultimately find applications which are not possible for porous solids, such as continuous flow separation processes. Type II PLs consist of empty molecular hosts dissolved in size-excluded solvents and to date have mainly been based on hosts that have limited chemical and thermal stability. Here we identify Noria, a rigid cyclic oligomer as a new host for the synthesis of more robust Type II PLs. Although the structure of Noria is well-documented, we find that literature has overlooked the true composition of bulk Noria samples. We find that bulk samples typically consist of Noria (ca.40%), a Noria isomer, specifically a resorcinarene trimer, “R3” (ca.30%) and other unidentified oligomers (ca.30%). Noria has been characterised crystallographically as a diethyl ether solvate and its1H NMR spectrum fully assigned for the first time. The previously postulated but unreported R3 has also been characterised crystallographically as a dimethyl sulfoxide solvate, which confirms its alternative connectivity to Noria. Noria and R3 have low solubility which precludes their use in Type II PLs, however, the partially ethylated derivative Noria-OEt dissolves in the size-excluded solvent 15-crown-5 to give a new Type II PL. This PL exhibits enhanced uptake of methane (CH4) gas supporting the presence of empty pores in the liquid. Detailed molecular dynamics simulations support the existence of pores in the liquid and show that occupation of the pores by CH4is favoured. Overall, this work revises the general accepted composition of bulk Noria samples and shows that Noria derivatives are appropriate for the synthesis of more robust Type II PLs.
Fil: Alexander, Francesca M.. The Queens University of Belfast; Irlanda
Fil: Fonrouge Kotik, Sergio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: Borioni, José Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: del Popolo, Mario Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto Interdisciplinario de Ciencias Básicas. - Universidad Nacional de Cuyo. Instituto Interdisciplinario de Ciencias Básicas; Argentina
Fil: Horton, Peter N.. University of Southampton; Reino Unido
Fil: Coles, Simon J.. University of Southampton; Reino Unido
Fil: Hutchings, Benjamin P.. The Queens University of Belfast; Irlanda
Fil: Crawford, Deborah E.. University of Bradford; Reino Unido
Fil: James, Stuart L.. The Queens University of Belfast; Irlanda
description Porous Liquids (PLs) are a new class of material that possess both fluidity and permanent porosity. As such they can act as enhanced, selective solvents and may ultimately find applications which are not possible for porous solids, such as continuous flow separation processes. Type II PLs consist of empty molecular hosts dissolved in size-excluded solvents and to date have mainly been based on hosts that have limited chemical and thermal stability. Here we identify Noria, a rigid cyclic oligomer as a new host for the synthesis of more robust Type II PLs. Although the structure of Noria is well-documented, we find that literature has overlooked the true composition of bulk Noria samples. We find that bulk samples typically consist of Noria (ca.40%), a Noria isomer, specifically a resorcinarene trimer, “R3” (ca.30%) and other unidentified oligomers (ca.30%). Noria has been characterised crystallographically as a diethyl ether solvate and its1H NMR spectrum fully assigned for the first time. The previously postulated but unreported R3 has also been characterised crystallographically as a dimethyl sulfoxide solvate, which confirms its alternative connectivity to Noria. Noria and R3 have low solubility which precludes their use in Type II PLs, however, the partially ethylated derivative Noria-OEt dissolves in the size-excluded solvent 15-crown-5 to give a new Type II PL. This PL exhibits enhanced uptake of methane (CH4) gas supporting the presence of empty pores in the liquid. Detailed molecular dynamics simulations support the existence of pores in the liquid and show that occupation of the pores by CH4is favoured. Overall, this work revises the general accepted composition of bulk Noria samples and shows that Noria derivatives are appropriate for the synthesis of more robust Type II PLs.
publishDate 2021
dc.date.none.fl_str_mv 2021-11
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/11336/173844
Alexander, Francesca M.; Fonrouge Kotik, Sergio Federico; Borioni, José Luis; del Popolo, Mario Gabriel; Horton, Peter N.; et al.; Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids; Royal Society of Chemistry; Chemical Science; 12; 42; 11-2021; 14230-14240
2041-6520
2041-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/173844
identifier_str_mv Alexander, Francesca M.; Fonrouge Kotik, Sergio Federico; Borioni, José Luis; del Popolo, Mario Gabriel; Horton, Peter N.; et al.; Noria and its derivatives as hosts for chemically and thermally robust Type II porous liquids; Royal Society of Chemistry; Chemical Science; 12; 42; 11-2021; 14230-14240
2041-6520
2041-6539
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://pubs.rsc.org/en/content/articlelanding/2021/SC/D1SC03367K
info:eu-repo/semantics/altIdentifier/doi/10.1039/d1sc03367k
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
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: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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score 13.22299

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