dc.contributor.author | Ximenis, Marta | |
dc.contributor.author | Monot, Julien | |
dc.contributor.author | Gabirondo Amenabar, Elena | |
dc.contributor.author | Jeschke, Janna | |
dc.contributor.author | Martín Vaca, Blanca | |
dc.contributor.author | Bourissou, Didier | |
dc.contributor.author | Sardon Muguruza, Haritz | |
dc.date.accessioned | 2024-04-30T13:40:11Z | |
dc.date.available | 2024-04-30T13:40:11Z | |
dc.date.issued | 2024-03 | |
dc.identifier.citation | Macromolecules 57(7) : 3319-3327 (2024) | es_ES |
dc.identifier.issn | 0024-9297 | |
dc.identifier.issn | 1520-5835 | |
dc.identifier.uri | http://hdl.handle.net/10810/66943 | |
dc.description.abstract | The development of new sustainable polymeric materials endowed with improved performances but minimal environmental impact is a major concern, with polyesters as primary targets. Lactones are key monomers thanks to ring-opening polymerization, but their use in step-growth polymerization has remained scarce and challenging. Herein, we report a powerful bis(γ-lactone) (γSL) that was efficiently prepared on a gram scale from malonic acid by Pd-catalyzed cycloisomerization. The γ-exomethylene moieties and the spiro structure greatly enhance its reactivity toward ring-opening and enable step-growth polymerization under mild conditions. Using diols, dithiols, or diamines as comonomers, a variety of regioregular (AB)n copolymers with diverse linkages and functional groups (from oxo-ester to β-thioether lactone and β-hydroxy-lactame) have been readily prepared. Reaction modeling and monitoring revealed the occurrence of an original trans-lactonization process following the first ring-opening of γSL. This peculiar reactivity opens the way to regioregular (ABAC)n terpolymers, as illustrated by the successive step-growth polymerization of γSL with a diol and a diamine. | es_ES |
dc.description.sponsorship | This work was supported financially by the Centre National de la Recherche Scientifique and the Université de Toulouse, Pascale Laborie (Saint-Aguet), and Marc Vedrenne (ICT, UAR2599) are acknowledged for their help in the nonroutine SEC and NMR analyses, respectively. H.S., E.G., and M.X. acknowledge the financial support from el Ministerio de Ciencia e Innovación from TED2021-129852B-C22 funded by MCIU/AEI/10.13039/501100011033 and by the European Union NextGenerationEU/PRTR and the grant PID2022-138199NB-I00 funded by MCIU/AEI/10.13039/501100011033. M.X. thanks the Gipuzkoa Fellows Programme (G75067454), and E.G. thanks the Basque Government for the Postdoctoral grant. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | ACS | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/TED2021-129852B-C22 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2022-138199NB-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es/ | * |
dc.subject | diols | es_ES |
dc.subject | lactones | es_ES |
dc.subject | reactivity | es_ES |
dc.subject | ring opening reactions | es_ES |
dc.subject | ring-opening polymerization | es_ES |
dc.title | Boosting the Reactivity of Bis-Lactones to Enable Step-Growth Polymerization at Room Temperature | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2024 The Authors. Published by American Chemical Society. This publication is licensed under
CC-BY 4.0. | es_ES |
dc.rights.holder | Atribución 3.0 España | * |
dc.relation.publisherversion | https://pubs.acs.org/doi/10.1021/acs.macromol.3c02527 | es_ES |
dc.identifier.doi | 10.1021/acs.macromol.3c02527 | |
dc.departamentoes | Polímeros y Materiales Avanzados: Física, Química y Tecnología | es_ES |
dc.departamentoeu | Polimero eta Material Aurreratuak: Fisika, Kimika eta Teknologia | es_ES |