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

The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based α-azide-ω-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 sele...

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Detalles Bibliográficos
Autores principales: Fidalgo, D.M., Kolender, A.A., Varela, O.
Formato: JOUR
Materias:
Biomaterials
Carbohydrate
Click polymerization
Polytriazole
Amides
Carbohydrates
Copper compounds
Hydrocarbons
Polymerization
Regioselectivity
Bio-based monomers
Microwave assisted
Polymer backbones
Random distribution
Renewable resource
Selective protection
Triazole linkages
Monomers
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_23524928_v2_n_pe70_Fidalgo
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_23524928_v2_n_pe70_Fidalgo
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spelling todo:paper_23524928_v2_n_pe70_Fidalgo2023-10-03T16:41:15Z Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers Fidalgo, D.M. Kolender, A.A. Varela, O. Biomaterials Carbohydrate Click polymerization Polytriazole Amides Biomaterials Carbohydrates Copper compounds Hydrocarbons Polymerization Regioselectivity Bio-based monomers Microwave assisted Polymer backbones Polytriazole Random distribution Renewable resource Selective protection Triazole linkages Monomers The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based α-azide-ω-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. © 2014 Elsevier Ltd. Fil:Kolender, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_23524928_v2_n_pe70_Fidalgo
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Biomaterials
Carbohydrate
Click polymerization
Polytriazole
Amides
Biomaterials
Carbohydrates
Copper compounds
Hydrocarbons
Polymerization
Regioselectivity
Bio-based monomers
Microwave assisted
Polymer backbones
Polytriazole
Random distribution
Renewable resource
Selective protection
Triazole linkages
Monomers
spellingShingle Biomaterials
Carbohydrate
Click polymerization
Polytriazole
Amides
Biomaterials
Carbohydrates
Copper compounds
Hydrocarbons
Polymerization
Regioselectivity
Bio-based monomers
Microwave assisted
Polymer backbones
Polytriazole
Random distribution
Renewable resource
Selective protection
Triazole linkages
Monomers
Fidalgo, D.M.
Kolender, A.A.
Varela, O.
Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
topic_facet Biomaterials
Carbohydrate
Click polymerization
Polytriazole
Amides
Biomaterials
Carbohydrates
Copper compounds
Hydrocarbons
Polymerization
Regioselectivity
Bio-based monomers
Microwave assisted
Polymer backbones
Polytriazole
Random distribution
Renewable resource
Selective protection
Triazole linkages
Monomers
description The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based α-azide-ω-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. © 2014 Elsevier Ltd.
format JOUR
author Fidalgo, D.M.
Kolender, A.A.
Varela, O.
author_facet Fidalgo, D.M.
Kolender, A.A.
Varela, O.
author_sort Fidalgo, D.M.
title Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
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
url http://hdl.handle.net/20.500.12110/paper_23524928_v2_n_pe70_Fidalgo
work_keys_str_mv AT fidalgodm polyamidetriazolesobtainedbyregioselectivemicrowaveassistedclickpolymerizationofbiobasedmonomers
AT kolenderaa polyamidetriazolesobtainedbyregioselectivemicrowaveassistedclickpolymerizationofbiobasedmonomers
AT varelao polyamidetriazolesobtainedbyregioselectivemicrowaveassistedclickpolymerizationofbiobasedmonomers
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