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Polymers from Sugars and Cyclic Anhydrides: Ring-Opening Copolymerization of a d-Xylose Anhydrosugar Oxetane

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Macromolecules 2021, 54, 11, 5094-5105
    Article

    Polymers from Sugars and Cyclic Anhydrides: Ring-Opening Copolymerization of a d-Xylose Anhydrosugar Oxetane
    Click to copy article linkArticle link copied!

    • Thomas M. McGuire
      Thomas M. McGuire
      Centre for Sustainable and Circular Technologies, Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.
      More by Thomas M. McGuire
    • Ella F. Clark
      Ella F. Clark
      Centre for Sustainable and Circular Technologies, Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.
      More by Ella F. Clark
    • Antoine Buchard*
      Antoine Buchard
      Centre for Sustainable and Circular Technologies, Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.
      *Email: [email protected]
      More by Antoine Buchard
      Orcidhttps://orcid.org/0000-0003-3417-5194
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    Macromolecules

    Cite this: Macromolecules 2021, 54, 11, 5094–5105
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    https://doi.org/10.1021/acs.macromol.1c00365
    Published May 18, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    A d-xylose 3,5-anhydrosugar derivative has been used as an oxetane co-monomer in the ring-opening copolymerization (ROCOP) with cyclic anhydrides, to form a family of seven novel sugar-derived polyesters, with up to 100% renewable content. ROCOP proceeds with high alternating selectivity to form AB-type copolymers that are thermally robust (Td,onset > 212 °C) and exhibit a broad range of glass-transition temperatures (Tg 60–145 °C). These polyesters are amenable to further postpolymerization functionalization. The hydroxy group of the sugar moiety can be unveiled, then functionalized further, e.g., phosphorylated. The internal alkene of some of the anhydride moieties can also be subject to thiol-ene reactions. Combining those orthogonal strategies affords AB copolyesters with alternating functional substituents. By exploiting the living character of the ROCOP process, block copolymers have also been synthesized through sequential co-monomer addition experiments.

    Copyright © 2021 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.1c00365.

    • Experimental and computational procedures; processed NMR spectra of monomer and polymers and associated digital repository with primary NMR spectroscopic data; plots of Mn and ĐM vs conversion, polymerization kinetic data, images of SEC traces, MALDI-ToF MS, TGA-MS, DSC traces, and WAXS profiles; and DFT calculation data and associated digital repository (PDF)

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    Cited By

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    This article is cited by 19 publications.

    1. Aya Katto, Sadahito Aoshima, Arihiro Kanazawa. Sugar-Derived Cyclic Acetals as Comonomers for Cationic Copolymerization with Vinyl Ethers. Macromolecules 2024, 57 (13) , 6255-6266. https://doi.org/10.1021/acs.macromol.4c00847
    2. Iyoka Ota, Ryota Suzuki, Yuta Mizukami, Xiaochao Xia, Kenji Tajima, Takuya Yamamoto, Feng Li, Takuya Isono, Toshifumi Satoh. Organobase-Catalyzed Ring-Opening Copolymerization of Cyclic Anhydrides and Oxetanes: Establishment and Application in Block Copolymer Synthesis. Macromolecules 2024, 57 (8) , 3741-3750. https://doi.org/10.1021/acs.macromol.3c02483
    3. Arianna Brandolese, David H. Lamparelli, Ilaria Grimaldi, Salvatore Impemba, Piero Baglioni, Arjan W. Kleij. Access to Functionalized Polycarbonates Derived from Fatty Acid Esters via Catalytic ROCOP and Their Potential in Gel Formulations. Macromolecules 2024, 57 (8) , 3816-3823. https://doi.org/10.1021/acs.macromol.4c00411
    4. Craig Hardy, Martin E. Levere, Gabriele Kociok-Köhn, Antoine Buchard. Radical Ring Opening Polymerization of Cyclic Ketene Acetals Derived From d-Glucal. ACS Macro Letters 2023, 12 (11) , 1443-1449. https://doi.org/10.1021/acsmacrolett.3c00397
    5. David K. Tran, Ashley N. Braaksma, Autumn M. Andras, Senthil K. Boopathi, Donald J. Darensbourg, Karen L. Wooley. Structural Metamorphoses of d-Xylose Oxetane- and Carbonyl Sulfide-Based Polymers In Situ during Ring-Opening Copolymerizations. Journal of the American Chemical Society 2023, 145 (33) , 18560-18567. https://doi.org/10.1021/jacs.3c05529
    6. David H. Lamparelli, Ilaria Grimaldi, Alicia Martínez-Carrión, Fernando Bravo, Arjan W. Kleij. Supercritical CO2 as an Efficient Medium for Macromolecular Carbonate Synthesis through Ring-Opening Co- and Teroligomerization. ACS Sustainable Chemistry & Engineering 2023, 11 (22) , 8193-8198. https://doi.org/10.1021/acssuschemeng.3c02002
    7. Sumin Lee, Woo Hyuk Jung, Minseong Kim, Dong June Ahn, Byeong-Su Kim. Tailoring the Interplay between Two Monomers in the Properties of Degradable Polyesters Synthesized via Ring-Opening Alternating Copolymerization. ACS Macro Letters 2023, 12 (5) , 590-597. https://doi.org/10.1021/acsmacrolett.3c00104
    8. Emma L. Daniels, James R. Runge, Matthew Oshinowo, Hannah S. Leese, Antoine Buchard. Cross-Linking of Sugar-Derived Polyethers and Boronic Acids for Renewable, Self-Healing, and Single-Ion Conducting Organogel Polymer Electrolytes. ACS Applied Energy Materials 2023, 6 (5) , 2924-2935. https://doi.org/10.1021/acsaem.2c03937
    9. Xiaochao Xia, Tianle Gao, Feng Li, Ryota Suzuki, Takuya Isono, Toshifumi Satoh. Multidimensional Control of Repeating Unit/Sequence/Topology for One-Step Synthesis of Block Polymers from Monomer Mixtures. Journal of the American Chemical Society 2022, 144 (39) , 17905-17915. https://doi.org/10.1021/jacs.2c06860
    10. Maria Varghese, Kaitlynn A. Sockett, Sara El-Arid, Jenny Korunes-Miller, Jean-Michel Guigner, Mark W. Grinstaff. Synthesis of Amphiphilic Diblock Poly-amido-saccharides and Self-Assembly of Polymeric Nanostructures. Macromolecules 2022, 55 (13) , 5675-5684. https://doi.org/10.1021/acs.macromol.2c00146
    11. Chang Qiao, Alba Villar-Yanez, Diego Garay-Ruiz, Jordi-Benet Buchholz, Carles Bo, Arjan W. Kleij. Domino Synthesis of Bicyclic 3,5-Anhydro Furanose Mimics Using a Binary Al(III) Complex/Halide Catalyst. ACS Catalysis 2022, 12 (9) , 5464-5469. https://doi.org/10.1021/acscatal.2c00925
    12. Ryan W. F. Kerr, Charlotte K. Williams. Zr(IV) Catalyst for the Ring-Opening Copolymerization of Anhydrides (A) with Epoxides (B), Oxetane (B), and Tetrahydrofurans (C) to Make ABB- and/or ABC-Poly(ester-alt-ethers). Journal of the American Chemical Society 2022, 144 (15) , 6882-6893. https://doi.org/10.1021/jacs.2c01225
    13. Lanlan Zheng, Jiabing Feng, Hongyan Xie, Zhiguang Xu. Organocatalytic synthesis of sugar‐derived polyesters via ring‐opening alternating copolymerization of anhydrosugar oxetane and anhydrides. Journal of Polymer Science 2023, 61 (14) , 1430-1438. https://doi.org/10.1002/pol.20230036
    14. Ella F. Clark, Gabriele Kociok-Köhn, Matthew G. Davidson, Antoine Buchard. Polymers from sugars and isothiocyanates: ring-opening copolymerization of a d -xylose anhydrosugar oxetane. Polymer Chemistry 2023, 14 (23) , 2838-2847. https://doi.org/10.1039/D3PY00443K
    15. Jing Wang, Ji Zhou, Yuzhuo Ding, Xiangguo Hu, Yiwang Chen. Glycopolymers based on carbohydrate or vinyl backbones and their biomedical applications. Polymer Chemistry 2023, 14 (20) , 2414-2434. https://doi.org/10.1039/D3PY00117B
    16. Wilfred T. Diment, Gloria Rosetto, Noura Ezaz-Nikpay, Ryan W. F. Kerr, Charlotte K. Williams. A highly active, thermally robust iron( iii )/potassium( i ) heterodinuclear catalyst for bio-derived epoxide/anhydride ring-opening copolymerizations. Green Chemistry 2023, 25 (6) , 2262-2267. https://doi.org/10.1039/D2GC04580J
    17. Xiaoqian Wang, Ziyu Huo, Xiaoyu Xie, Narasimhamurthy Shanaiah, Rong Tong. Recent Advances in Sequence‐Controlled Ring‐Opening Copolymerizations of Monomer Mixtures. Chemistry – An Asian Journal 2023, 18 (4) https://doi.org/10.1002/asia.202201147
    18. Craig Hardy, Gabriele Kociok-Köhn, Antoine Buchard. Variations around the presence and position of sulfur in sugar-derived cyclic monomers: influence on polymerisation thermodynamics, polymer sequence and thermal properties. Polymer Chemistry 2023, 14 (5) , 623-632. https://doi.org/10.1039/D2PY01366E
    19. Thomas M. McGuire, Antoine Buchard. Polymers from sugars and CS 2 : ring opening copolymerisation of a d -xylose anhydrosugar oxetane. Polymer Chemistry 2021, 12 (29) , 4253-4261. https://doi.org/10.1039/D1PY00753J
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    Macromolecules

    Cite this: Macromolecules 2021, 54, 11, 5094–5105
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.macromol.1c00365
    Published May 18, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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