Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels

Gelation of organic solvents using N,N′-((1S,2S)-cyclohexane-1,2-diyl)didodecanamide (C12–Cyc) is driven by its self-assembly via antiparallel hydrogen bonds and van der Waals intermolecular interactions. In this work we carried out a dual isosteric substitution of the two amide groups with 1,2,3-tr...

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Autores: Tautz, Markus, Torras, Juan, Grijalvo, Santiago, Eritja Casadellà, Ramón, Saldías, César, Alemán, Carlos, Díaz Díaz, David
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2019
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositório:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/185517
Acesso em linha:http://hdl.handle.net/10261/185517
Access Level:Acceso aberto
Palavra-chave:Physical gels
Gelation
Organic solvents
Amide–triazole isosteric substitution
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spelling Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gelsTautz, MarkusTorras, JuanGrijalvo, SantiagoEritja Casadellà, RamónSaldías, CésarAlemán, CarlosDíaz Díaz, DavidPhysical gelsGelationOrganic solventsAmide–triazole isosteric substitutionGelation of organic solvents using N,N′-((1S,2S)-cyclohexane-1,2-diyl)didodecanamide (C12–Cyc) is driven by its self-assembly via antiparallel hydrogen bonds and van der Waals intermolecular interactions. In this work we carried out a dual isosteric substitution of the two amide groups with 1,2,3-triazole rings affording the corresponding isosteric gelator (click-C12–Cyc). A detailed comparative study in terms of the gelation ability and gel properties demonstrated that the 1,2,3-triazoles can take over all of the functions derived from the amide groups offering a versatile strategy for tuning the properties of the corresponding gels. This is not an obvious outcome because the directional amide groups in C12–Cyc constitute the source of the hydrogen bonds to build the 3D self-assembled network. Furthermore, theoretical calculations revealed that click-C12–Cyc can adopt a wide variety of interacting patterns, whose relative stability depends on the polarity of the environment, this is in good agreement with the experimental data obtained regarding its gelation ability. Other important features of click-C12–Cyc for potential practical applications are its non-cytotoxic character and its phase-selective gelation of water–oil mixtures.This work was supported by the University of Regensburg, the Deutsche Forschungsgemeinschaft (DFG), Generalitat de Catalunya (SGR/264), Instituto de Salud Carlos III (ISCIII) (CB06_01_0019); Ministerio de Economía, Industria y Competitividad (MINECO) (CTQ2014-52588-R and CTQ2017-84415-R) and European FEDER funds (MAT2015-69367-R), the Agència de Gestió d'Ajuts Universitaris i de Recerca (2017SGR359 and XRTQC), and Fondecyt iniciación 11160707. Support for the research of C. A. was received through the prize “ICREA Academia” for excellence in research funded by the Generalitat de Catalunya. D. D. D. thanks the DFG for the Heisenberg Professorship Award.Peer reviewedRoyal Society of Chemistry (UK)Ministerio de Economía y Competitividad (España)Eritja Casadellà, Ramón [0000-0001-5383-9334]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/185517reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52588-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84415-Rhttps://doi.org/10.1039/C9RA03316ESíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1855172026-05-22T06:33:51Z
dc.title.none.fl_str_mv Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
title Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
spellingShingle Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
Tautz, Markus
Physical gels
Gelation
Organic solvents
Amide–triazole isosteric substitution
title_short Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
title_full Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
title_fullStr Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
title_full_unstemmed Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
title_sort Expanding the limits of amide–triazole isosteric substitution in bisamide-based physical gels
dc.creator.none.fl_str_mv Tautz, Markus
Torras, Juan
Grijalvo, Santiago
Eritja Casadellà, Ramón
Saldías, César
Alemán, Carlos
Díaz Díaz, David
author Tautz, Markus
author_facet Tautz, Markus
Torras, Juan
Grijalvo, Santiago
Eritja Casadellà, Ramón
Saldías, César
Alemán, Carlos
Díaz Díaz, David
author_role author
author2 Torras, Juan
Grijalvo, Santiago
Eritja Casadellà, Ramón
Saldías, César
Alemán, Carlos
Díaz Díaz, David
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Eritja Casadellà, Ramón [0000-0001-5383-9334]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Physical gels
Gelation
Organic solvents
Amide–triazole isosteric substitution
topic Physical gels
Gelation
Organic solvents
Amide–triazole isosteric substitution
description Gelation of organic solvents using N,N′-((1S,2S)-cyclohexane-1,2-diyl)didodecanamide (C12–Cyc) is driven by its self-assembly via antiparallel hydrogen bonds and van der Waals intermolecular interactions. In this work we carried out a dual isosteric substitution of the two amide groups with 1,2,3-triazole rings affording the corresponding isosteric gelator (click-C12–Cyc). A detailed comparative study in terms of the gelation ability and gel properties demonstrated that the 1,2,3-triazoles can take over all of the functions derived from the amide groups offering a versatile strategy for tuning the properties of the corresponding gels. This is not an obvious outcome because the directional amide groups in C12–Cyc constitute the source of the hydrogen bonds to build the 3D self-assembled network. Furthermore, theoretical calculations revealed that click-C12–Cyc can adopt a wide variety of interacting patterns, whose relative stability depends on the polarity of the environment, this is in good agreement with the experimental data obtained regarding its gelation ability. Other important features of click-C12–Cyc for potential practical applications are its non-cytotoxic character and its phase-selective gelation of water–oil mixtures.
publishDate 2019
dc.date.none.fl_str_mv 2019
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/185517
url http://hdl.handle.net/10261/185517
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52588-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84415-R
https://doi.org/10.1039/C9RA03316E
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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