Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers.
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/8639 https://doi.org/10.1016/j.eurpolymj.2017.03.028 |
Resumo: | A versatile and simple strategy is presented to synthesize reactive polylactide derivatives and their block copolymers with polyethylene glycol. Commercially available glycidyl ethers with an allyl, benzyl or propargyl functional group were copolymerised with D,L-lactide. Tin(II)-2- ethylhexanoate-catalysis produced polymers with up to 4.6, 5.9 and 2.3 allyl, benzyl or propargyl groups per chain, respectively. In contrast, less than one reactive group per chain was obtained with the organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene. By increasing the polymerisation feed ratio in glycidyl ether polymers with a higher number of reactive groups per chain were obtained, however a decrease in molar mass was observed. An azidocoumarin was conjugated to the propargylated polymers via copper-catalysed azide-alkyne cycloaddition. These dye-labelled polymers produced nanospheres with fluorescent properties and diameters in the 100-nm sizerange, as characterised by asymmetric flow field flow fractionation hyphenated with fluorescence, static and dynamic light scattering detection. The functionalised polymers were obtained at gram-scale in one step from commercially available reagents; therefore providing a robust and easy to implement approach for the production of multifunctional nanomaterials. |
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Lana, Gwenaelle Elza Nathalie PoundRabanel, Jean MichelHildgen, PatriceMosqueira, Vanessa Carla Furtado2017-08-31T15:57:09Z2017-08-31T15:57:09Z2017LANA, G. E. N. P. et al. Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. European Polymer Journal, v. 90, p. 344-353, 2017. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0014305717300447>. Acesso em: 29 ago. 2017.0014-3057http://www.repositorio.ufop.br/handle/123456789/8639https://doi.org/10.1016/j.eurpolymj.2017.03.028A versatile and simple strategy is presented to synthesize reactive polylactide derivatives and their block copolymers with polyethylene glycol. Commercially available glycidyl ethers with an allyl, benzyl or propargyl functional group were copolymerised with D,L-lactide. Tin(II)-2- ethylhexanoate-catalysis produced polymers with up to 4.6, 5.9 and 2.3 allyl, benzyl or propargyl groups per chain, respectively. In contrast, less than one reactive group per chain was obtained with the organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene. By increasing the polymerisation feed ratio in glycidyl ether polymers with a higher number of reactive groups per chain were obtained, however a decrease in molar mass was observed. An azidocoumarin was conjugated to the propargylated polymers via copper-catalysed azide-alkyne cycloaddition. These dye-labelled polymers produced nanospheres with fluorescent properties and diameters in the 100-nm sizerange, as characterised by asymmetric flow field flow fractionation hyphenated with fluorescence, static and dynamic light scattering detection. The functionalised polymers were obtained at gram-scale in one step from commercially available reagents; therefore providing a robust and easy to implement approach for the production of multifunctional nanomaterials.O periódico European Polymer Journal concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 4178720595540.info:eu-repo/semantics/openAccessEpoxidePolymer-conjugateFluorescent probeAzide-alkyne cycloadditionPolymeric nanoparticlesFunctional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-8924http://www.repositorio.ufop.br/bitstream/123456789/8639/2/license.txt62604f8d955274beb56c80ce1ee5dcaeMD52ORIGINALARTIGO_FuctionalPolylactideVia.pdfARTIGO_FuctionalPolylactideVia.pdfapplication/pdf748602http://www.repositorio.ufop.br/bitstream/123456789/8639/1/ARTIGO_FuctionalPolylactideVia.pdf07b0096d0e794e7a81b16187210bf55cMD51123456789/86392020-01-23 09:11:29.034oai:localhost: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ório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332020-01-23T14:11:29Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
title |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
spellingShingle |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. Lana, Gwenaelle Elza Nathalie Pound Epoxide Polymer-conjugate Fluorescent probe Azide-alkyne cycloaddition Polymeric nanoparticles |
title_short |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
title_full |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
title_fullStr |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
title_full_unstemmed |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
title_sort |
Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. |
author |
Lana, Gwenaelle Elza Nathalie Pound |
author_facet |
Lana, Gwenaelle Elza Nathalie Pound Rabanel, Jean Michel Hildgen, Patrice Mosqueira, Vanessa Carla Furtado |
author_role |
author |
author2 |
Rabanel, Jean Michel Hildgen, Patrice Mosqueira, Vanessa Carla Furtado |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Lana, Gwenaelle Elza Nathalie Pound Rabanel, Jean Michel Hildgen, Patrice Mosqueira, Vanessa Carla Furtado |
dc.subject.por.fl_str_mv |
Epoxide Polymer-conjugate Fluorescent probe Azide-alkyne cycloaddition Polymeric nanoparticles |
topic |
Epoxide Polymer-conjugate Fluorescent probe Azide-alkyne cycloaddition Polymeric nanoparticles |
description |
A versatile and simple strategy is presented to synthesize reactive polylactide derivatives and their block copolymers with polyethylene glycol. Commercially available glycidyl ethers with an allyl, benzyl or propargyl functional group were copolymerised with D,L-lactide. Tin(II)-2- ethylhexanoate-catalysis produced polymers with up to 4.6, 5.9 and 2.3 allyl, benzyl or propargyl groups per chain, respectively. In contrast, less than one reactive group per chain was obtained with the organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene. By increasing the polymerisation feed ratio in glycidyl ether polymers with a higher number of reactive groups per chain were obtained, however a decrease in molar mass was observed. An azidocoumarin was conjugated to the propargylated polymers via copper-catalysed azide-alkyne cycloaddition. These dye-labelled polymers produced nanospheres with fluorescent properties and diameters in the 100-nm sizerange, as characterised by asymmetric flow field flow fractionation hyphenated with fluorescence, static and dynamic light scattering detection. The functionalised polymers were obtained at gram-scale in one step from commercially available reagents; therefore providing a robust and easy to implement approach for the production of multifunctional nanomaterials. |
publishDate |
2017 |
dc.date.accessioned.fl_str_mv |
2017-08-31T15:57:09Z |
dc.date.available.fl_str_mv |
2017-08-31T15:57:09Z |
dc.date.issued.fl_str_mv |
2017 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
LANA, G. E. N. P. et al. Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. European Polymer Journal, v. 90, p. 344-353, 2017. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0014305717300447>. Acesso em: 29 ago. 2017. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/8639 |
dc.identifier.issn.none.fl_str_mv |
0014-3057 |
dc.identifier.doi.none.fl_str_mv |
https://doi.org/10.1016/j.eurpolymj.2017.03.028 |
identifier_str_mv |
LANA, G. E. N. P. et al. Functional polylactide via ring-opening copolymerisation with allyl, benzyl and propargyl glycidyl ethers. European Polymer Journal, v. 90, p. 344-353, 2017. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0014305717300447>. Acesso em: 29 ago. 2017. 0014-3057 |
url |
http://www.repositorio.ufop.br/handle/123456789/8639 https://doi.org/10.1016/j.eurpolymj.2017.03.028 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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reponame:Repositório Institucional da UFOP instname:Universidade Federal de Ouro Preto (UFOP) instacron:UFOP |
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