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Backbone Degradation of Polymethacrylates via Metal-Free Ambient-Temperature Photoinduced Single-Electron Transfer

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    Backbone Degradation of Polymethacrylates via Metal-Free Ambient-Temperature Photoinduced Single-Electron Transfer
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    • John B. Garrison
      John B. Garrison
      George & Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science & Engineering, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States
      More by John B. Garrison
    • Rhys W. Hughes
      Rhys W. Hughes
      George & Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science & Engineering, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States
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    • Brent S. Sumerlin*
      Brent S. Sumerlin
      George & Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science & Engineering, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0001-5749-5444
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    ACS Macro Letters

    Cite this: ACS Macro Lett. 2022, 11, 4, 441–446
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    https://doi.org/10.1021/acsmacrolett.2c00091
    Published March 15, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    Polymeric materials comprised of all-carbon backbones are ubiquitous to modern society due to their low cost, impressive robustness, and unparalleled physical properties. It is well-known that these materials often persist long beyond their intended usage lifetime, resulting in environmental accumulation of plastic waste. A substantial barrier to the breakdown of these polymers is the relative chemical inertness of carbon–carbon bonds within their backbone. Herein, we describe a photocatalytic strategy for cleaving carbon-based polymer backbones. Inclusion of a low mole percent of a redox-active comonomer allows for a dramatic reduction in polymer molecular weight upon exposure to light. The N-(acyloxy)phthalimide comonomer, upon reception of an electron from a single-electron transfer (SET) donor, undergoes decarboxylation to yield a backbone-centered radical. Depending on the nature of this backbone radical, as well as the substitution on neighboring monomer repeat units, a β-scission pathway is thermodynamically favored, resulting in backbone cleavage. In this way, polymers with an all-carbon backbone may be degraded at ambient temperature under metal-free conditions.

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    • Materials, instrumentation, methods, 1H NMR spectra for all compounds, and GPC elugrams for all polymers (PDF)

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    ACS Macro Letters

    Cite this: ACS Macro Lett. 2022, 11, 4, 441–446
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsmacrolett.2c00091
    Published March 15, 2022
    Copyright © 2022 American Chemical Society
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