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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Autores principales:	Kolender, Adriana Andrea, Varela, Oscar José
Publicado:	2015
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:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23524928_v2_n_pe70_Fidalgo 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	paper:paper_23524928_v2_n_pe70_Fidalgo
record_format	dspace
spelling	paper:paper_23524928_v2_n_pe70_Fidalgo2023-06-08T16:35:49Z Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers Kolender, Adriana Andrea Varela, Oscar José 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. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23524928_v2_n_pe70_Fidalgo 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 Kolender, Adriana Andrea Varela, Oscar José 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.
author	Kolender, Adriana Andrea Varela, Oscar José
author_facet	Kolender, Adriana Andrea Varela, Oscar José
author_sort	Kolender, Adriana Andrea
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
publishDate	2015
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23524928_v2_n_pe70_Fidalgo http://hdl.handle.net/20.500.12110/paper_23524928_v2_n_pe70_Fidalgo
work_keys_str_mv	AT kolenderadrianaandrea polyamidetriazolesobtainedbyregioselectivemicrowaveassistedclickpolymerizationofbiobasedmonomers AT varelaoscarjose polyamidetriazolesobtainedbyregioselectivemicrowaveassistedclickpolymerizationofbiobasedmonomers
_version_	1768545997405814784

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

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