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

Panagiotis Bexis; Jonathan Husband; Haritz Sardon; Haritz Sardon; Olivier Coulembier; Andrew Dove

doi:10.1021/acs.macromol.3c02485

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

Panagiotis Bexis, Jonathan Husband, Haritz Sardon, Haritz Sardon, Olivier Coulembier^*, Andrew Dove^*

^*Corresponding author for this work

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
Article number	3c02485
Pages (from-to)	2287-2294
Number of pages	9
Journal	Macromolecules
Volume	57
Issue number	5
Early online date	28 Feb 2024
DOIs	https://doi.org/10.1021/acs.macromol.3c02485
Publication status	Published - 12 Mar 2024

Bibliographical note

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.

Keywords

biodegradable
biocompatible
thermomechanical
stereocomplexation

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10.1021/acs.macromol.3c02485Licence: Creative Commons: Attribution (CC BY)

BexisP2024StereocomplexedFinal published version, 3.4 MBLicence: Creative Commons: Attribution (CC BY)

H2020_ERC_STEREOPOL
Dove, A.
European Commission
1/01/18 → 30/04/23
Project: EU

Cite this

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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.",

keywords = "biodegradable, biocompatible, thermomechanical, stereocomplexation",

author = "Panagiotis Bexis and Jonathan Husband and Haritz Sardon and Haritz Sardon and Olivier Coulembier and Andrew Dove",

note = "Funding This project has received funding to support P.B. from the European Union{\textquoteright}s Horizon 2020 research and innovation program under the Marie Sk{\l}odowska-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{\textquoteright}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.",

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T1 - Stereocomplexed Functional and Statistical Poly(lactide-carbonate)s via a Simple Organocatalytic System

AU - Bexis, Panagiotis

AU - Husband, Jonathan

AU - Sardon, Haritz

AU - Coulembier, Olivier

AU - Dove, Andrew

N1 - 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.

PY - 2024/3/12

Y1 - 2024/3/12

N2 - 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.

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.

KW - biodegradable

KW - biocompatible

KW - thermomechanical

KW - stereocomplexation

U2 - 10.1021/acs.macromol.3c02485

DO - 10.1021/acs.macromol.3c02485

M3 - Article

SN - 0024-9297

VL - 57

SP - 2287

EP - 2294

JO - Macromolecules

JF - Macromolecules

IS - 5

M1 - 3c02485

ER -

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

Abstract

Bibliographical note

Keywords

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Projects

H2020_ERC_STEREOPOL

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