Stereocomplexed Functional and Statistical Poly (lactide-carbonate) s via a Simple Organocatalytic System

Panagiotis Bexis; Jon Husband; Haritz Sardon; Olivier Coulembier; Andrew P. Dove

doi:10.1021/acs.macromol.3c02485

Stereocomplexed Functional and Statistical Poly (lactide-carbonate) s via a Simple Organocatalytic System

Panagiotis Bexis, Jon Husband, Haritz Sardon, Olivier Coulembier, Andrew P. Dove

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The stereocomplexation of polylactide (PLA) has been widely relied upon to develop degradable, sustainable materials with increased strength and improved material properties in comparison to stereopure PLA. However, forming functionalized copolymers of PLA while retaining high crystallinity remains elusive. Herein, the controlled ring-opening copolymerization (ROCOP) of lactide (LA) and functionalized cyclic carbonate monomers is undertaken. The produced polymers are shown to remain crystalline up to 25 mol % carbonate content and are efficiently stereocomplexed with homopolymer PLA and copolymers of opposite chirality. Polymers with alkene and alkyne pendent handles are shown to undergo efficient derivatization with thiol–ene click chemistry, which would allow both the covalent conjugation of therapeutic moieties and tuning of material properties.

Original language	English
Number of pages	8
Journal	Macromolecules
DOIs	https://doi.org/10.1021/acs.macromol.3c02485
Publication status	Published - 28 Feb 2024

Funding

This project has received funding to support P.B. from the European Union’s Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement No 642671(SUSPOL-EJD). A.P.D. and J.T.H. acknowledge the funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program under the grant agreement no. 681559. H.S. ackowledges grant PID2022-138199NB-I00 funded by MCIN/AEI/10.13039/501100011033 and grant TED2021-129852B-C22 funded by MCIN/AEI/10.13039/501100011033 and by the European Union NextGenerationEU/PRTR.

Funders	Funder number
European Union's Horizon 2020 - Research and Innovation Framework Programme	642671(SUSPOL-EJD), 681559

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title = "Stereocomplexed Functional and Statistical Poly (lactide-carbonate) s via a Simple Organocatalytic System",

abstract = "The stereocomplexation of polylactide (PLA) has been widely relied upon to develop degradable, sustainable materials with increased strength and improved material properties in comparison to stereopure PLA. However, forming functionalized copolymers of PLA while retaining high crystallinity remains elusive. Herein, the controlled ring-opening copolymerization (ROCOP) of lactide (LA) and functionalized cyclic carbonate monomers is undertaken. The produced polymers are shown to remain crystalline up to 25 mol % carbonate content and are efficiently stereocomplexed with homopolymer PLA and copolymers of opposite chirality. Polymers with alkene and alkyne pendent handles are shown to undergo efficient derivatization with thiol–ene click chemistry, which would allow both the covalent conjugation of therapeutic moieties and tuning of material properties.",

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AU - Sardon, Haritz

AU - Coulembier, Olivier

AU - Dove, Andrew P.

PY - 2024/2/28

Y1 - 2024/2/28

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AB - The stereocomplexation of polylactide (PLA) has been widely relied upon to develop degradable, sustainable materials with increased strength and improved material properties in comparison to stereopure PLA. However, forming functionalized copolymers of PLA while retaining high crystallinity remains elusive. Herein, the controlled ring-opening copolymerization (ROCOP) of lactide (LA) and functionalized cyclic carbonate monomers is undertaken. The produced polymers are shown to remain crystalline up to 25 mol % carbonate content and are efficiently stereocomplexed with homopolymer PLA and copolymers of opposite chirality. Polymers with alkene and alkyne pendent handles are shown to undergo efficient derivatization with thiol–ene click chemistry, which would allow both the covalent conjugation of therapeutic moieties and tuning of material properties.

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DO - 10.1021/acs.macromol.3c02485

M3 - Article

SN - 0024-9297

JO - Macromolecules

JF - Macromolecules

ER -

Stereocomplexed Functional and Statistical Poly (lactide-carbonate) s via a Simple Organocatalytic System

Abstract

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