Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers

Autores
Fidalgo, Daniela Marina; Kolender, Adriana Andrea; Varela, Oscar Jose
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based -azide--alkyne monomers afforded, with high regioselectivity, stereoregular poly(amide-triazole)s. The monomers were prepared starting from d-glucono-1,5-lactone as a renewable resource. The synthetic route involves the selective protection of this sugar lactone with formaldehyde to give a gluconic acid derivative, which was subjected to amidation of the carboxylic acid function with alkynylamines (2-propynyl, 3-butynyl, and 4-pentynylamines) and substitution of the primary hydroxyl group by azide. The regioselective click polymerization of these AB-type alkyne/azide monomers led to a series of linear biosourced poly(amide-triazole)s containing mostly (>95%) 1,4-disubstituted triazole linkages. In contrast, the thermal, metal-free click polymerization led to random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The length of the methylene chain linked to the amide of the monomer and the cycloaddition regioselectivity strongly affected the properties of the materials, mainly the Tg values, which were unexpectedly high.
Fil: Fidalgo, Daniela Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
Biomaterials
Click Polymerization
Polytriazole
Carbohydrate
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:11336/17723
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomersFidalgo, Daniela MarinaKolender, Adriana AndreaVarela, Oscar JoseBiomaterialsClick PolymerizationPolytriazoleCarbohydratehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based -azide--alkyne monomers afforded, with high regioselectivity, stereoregular poly(amide-triazole)s. The monomers were prepared starting from d-glucono-1,5-lactone as a renewable resource. The synthetic route involves the selective protection of this sugar lactone with formaldehyde to give a gluconic acid derivative, which was subjected to amidation of the carboxylic acid function with alkynylamines (2-propynyl, 3-butynyl, and 4-pentynylamines) and substitution of the primary hydroxyl group by azide. The regioselective click polymerization of these AB-type alkyne/azide monomers led to a series of linear biosourced poly(amide-triazole)s containing mostly (>95%) 1,4-disubstituted triazole linkages. In contrast, the thermal, metal-free click polymerization led to random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The length of the methylene chain linked to the amide of the monomer and the cycloaddition regioselectivity strongly affected the properties of the materials, mainly the Tg values, which were unexpectedly high.Fil: Fidalgo, Daniela Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaElsevier2015-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/17723Fidalgo, Daniela Marina; Kolender, Adriana Andrea; Varela, Oscar Jose; Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers; Elsevier; Materials Today Communications; 2; 3-2015; e70-e832352-4928enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.mtcomm.2014.12.001info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S2352492814000191info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:36Zoai:ri.conicet.gov.ar:11336/17723instacron: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 10:09:36.349CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
title Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
spellingShingle Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
Fidalgo, Daniela Marina
Biomaterials
Click Polymerization
Polytriazole
Carbohydrate
title_short Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
title_full Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
title_fullStr Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
title_full_unstemmed Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
title_sort Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
dc.creator.none.fl_str_mv Fidalgo, Daniela Marina
Kolender, Adriana Andrea
Varela, Oscar Jose
author Fidalgo, Daniela Marina
author_facet Fidalgo, Daniela Marina
Kolender, Adriana Andrea
Varela, Oscar Jose
author_role author
author2 Kolender, Adriana Andrea
Varela, Oscar Jose
author2_role author
author
dc.subject.none.fl_str_mv Biomaterials
Click Polymerization
Polytriazole
Carbohydrate
topic Biomaterials
Click Polymerization
Polytriazole
Carbohydrate
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based -azide--alkyne monomers afforded, with high regioselectivity, stereoregular poly(amide-triazole)s. The monomers were prepared starting from d-glucono-1,5-lactone as a renewable resource. The synthetic route involves the selective protection of this sugar lactone with formaldehyde to give a gluconic acid derivative, which was subjected to amidation of the carboxylic acid function with alkynylamines (2-propynyl, 3-butynyl, and 4-pentynylamines) and substitution of the primary hydroxyl group by azide. The regioselective click polymerization of these AB-type alkyne/azide monomers led to a series of linear biosourced poly(amide-triazole)s containing mostly (>95%) 1,4-disubstituted triazole linkages. In contrast, the thermal, metal-free click polymerization led to random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The length of the methylene chain linked to the amide of the monomer and the cycloaddition regioselectivity strongly affected the properties of the materials, mainly the Tg values, which were unexpectedly high.
Fil: Fidalgo, Daniela Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based -azide--alkyne monomers afforded, with high regioselectivity, stereoregular poly(amide-triazole)s. The monomers were prepared starting from d-glucono-1,5-lactone as a renewable resource. The synthetic route involves the selective protection of this sugar lactone with formaldehyde to give a gluconic acid derivative, which was subjected to amidation of the carboxylic acid function with alkynylamines (2-propynyl, 3-butynyl, and 4-pentynylamines) and substitution of the primary hydroxyl group by azide. The regioselective click polymerization of these AB-type alkyne/azide monomers led to a series of linear biosourced poly(amide-triazole)s containing mostly (>95%) 1,4-disubstituted triazole linkages. In contrast, the thermal, metal-free click polymerization led to random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The length of the methylene chain linked to the amide of the monomer and the cycloaddition regioselectivity strongly affected the properties of the materials, mainly the Tg values, which were unexpectedly high.
publishDate 2015
dc.date.none.fl_str_mv 2015-03
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/11336/17723
Fidalgo, Daniela Marina; Kolender, Adriana Andrea; Varela, Oscar Jose; Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers; Elsevier; Materials Today Communications; 2; 3-2015; e70-e83
2352-4928
url http://hdl.handle.net/11336/17723
identifier_str_mv Fidalgo, Daniela Marina; Kolender, Adriana Andrea; Varela, Oscar Jose; Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers; Elsevier; Materials Today Communications; 2; 3-2015; e70-e83
2352-4928
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.mtcomm.2014.12.001
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S2352492814000191
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 13.13397

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