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RESEARCH PAPER · Journal of the American Chemical Society · 2021

Depolymerization of Hydroxylated Polymers via Light-Driven C–C Bond Cleavage

Suong T. Nguyen, Elizabeth A. McLoughlin, James H. Cox, Brett P. Fors, Robert R. Knowles

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Depolymerization of Hydroxylated Polymers via Light-Driven C–C Bond CleavageOriginalTransforming superabsorbant polymers to super sticky notes0Sunlight‐Mediated Degradation of Polyethylene under the Synergy of Photothermal CH Activation and Modification14Metal-Catalyzed Switching Degradation of Vinyl Polymers via Introduction of an “In-Chain” Carbon–Halogen Bond as the Trigger69Applications of Photoredox Catalysis for the Radical-Induced Cleavage of C–C Bonds39Visible-light-driven polymerization towards the green synthesis of plastics47Contra-Thermodynamic Positional Isomerization of Olefins93Hypervalent-iodine promoted selective cleavage of C(sp 3 )–C(sp 3 ) bonds in ethers9Photoredox/persistent radical cation dual catalysis for alkoxy radical generation from alcohols20Catalytic carbon and hydrogen cycles in plastics chemistry78Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing33Towards Upcycling Biomass‐Derived Crosslinked Polymers with Light19Towards Upcycling Biomass‐Derived Crosslinked Polymers with Light3Cyanamide as a Highly Efficient Organocatalyst for the Glycolysis Recycling of PET103Plastic Waste Valorization by Leveraging Multidisciplinary Catalytic Technologies169Sustainably Recycling and Upcycling of Single-Use Plastic Wastes through Heterogeneous Catalysis32Solar-driven catalytic plastic upcycling87Polyolefin Innovations toward Circularity and Sustainable Alternatives96Recycling and Upgrading Utilization of Polymer Plastics †34New insights into urethane alcoholysis enable chemical full recycling of blended fabric waste65N -Haloimide-enabled halogenation via halogen-bond-assisted C–C activation of alkanols15Progress and perspective for conversion of plastic wastes into valuable chemicals395Mechanistic insights into the photocatalytic valorization of lignin models via C−O/C−C cleavage or C−C/C−N coupling41Rapid and Selective Photo‐degradation of Polymers: Design of an Alternating Copolymer with an o‐Nitrobenzyl Ether Pendant22Rapid and Selective Photo‐degradation of Polymers: Design of an Alternating Copolymer with an o‐Nitrobenzyl Ether Pendant0Detoxification of bisphenol A via sulfur-mediated carbon–carbon σ-bond scission15Visible light-mediated hydrogen atom transfer and proton transfer for the conversion of (2-vinylaryl)methanol derivatives to aryl aldehydes or aryl ketones5Depolymerization of robust polyetheretherketone to regenerate monomer units using sulfur reagents26Constructing stable “bridge” structures with compatibilizer POE‐g‐GMA to improve the compatibility of starch‐based composites12β-Scission by Direct Electrochemical Oxidation: Proton-coupled Electron Transfer Mechanism Dictated by Synthetic Study and Computations3Visible Light Induced Degradation of Poly(methyl methacrylate‐ co ‐methyl α ‐chloro acrylate) Copolymer at Ambient Temperature23Hydrogen Atom Transfer for C(sp3)−H Functionalization Enabled by Photoredox/Thianthrene/Methanol Synergistic Catalysis6Rational design of photo− /electro−catalytic systems for the transformation of plastic wastes51Sustainable catalytic strategies for the transformation of plastic wastes into valued products53Photocatalysis as an Effective Tool for Upcycling Polymers into Value‐Added Molecules87Photocatalysis as an Effective Tool for Upcycling Polymers into Value‐Added Molecules4FeCl3-Promoted Photocatalytic Cleavage of Cα–Cβ Bond in Lignin and Lignin Model to Aromatic Monomers0Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins3Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins87Chemical Recycling of Thiol Epoxy Thermosets via Light-Driven C–C Bond Cleavage81Metal free, white LED induced, room temperature degradation of methyl methacrylate - Methyl haloacrylate copolymers13Donor–Acceptor Covalent Organic Frameworks as a Heterogeneous Photoredox Catalyst for Scissoring Alkenes to Carbonyl Constituents13Unlocking Circularity Through the Chemical Recycling and Upcycling of Lignin-Derivable Polymethacrylates17Selective Electrocatalytic Degradation of Ether‐Containing Polymers31Selective Electrocatalytic Degradation of Ether‐Containing Polymers1Solvent–base mismatch enables the deconstruction of epoxy polymers and bisphenol A recovery41The thermodynamics and kinetics of depolymerization: what makes vinyl monomer regeneration feasible?98Photochemical Upcycling/Modification of Polystyrene-based Plastic Waste8β-Scission of Secondary Alcohols via Photosensitization: Synthetic Utilization and Mechanistic Insights27Chemical recycling of bromine-terminated polymers synthesized by ATRP26Controlled degradation of chemically stable poly(aryl ethers) via directing group-assisted catalysis6Photochemical upcycling and recycling of plastics: achievements and future opportunities56Plastonomics: Impact of Plastic on Ecosystem and the World Economy9Selectively self-recyclable, highly transparent and fire-safe polycarbonate plastic enabled by thermally responsive phosphonium-phosphate13Alcoholysis of oxyphenylene-based super engineering plastics mediated by readily available bases11Surface and interface engineering of BiOCl nanomaterials and their photocatalytic applications122Controlling photodegradation in vinyl ketone polymers12Photocatalytic Conversion of Lignin Models into Functionalized Aromatic Molecules Initiated by the Proton-Coupled Electron Transfer Process12Photodegradable Dynamic Polyurethane Networks via Dithioacetals29Catalytic thiolation-depolymerization-like decomposition of oxyphenylene-type super engineering plastics via selective carbon–oxygen main chain cleavages11Light-driven polymer recycling to monomers and small molecules112Perspective on the Development of Monomer Recovery Technologies from Plastics Designed to Last28Positioning dynamic polymeric materials within the modern polymer economy: From application to recycling and circularity10Catalytic chemical recycling and upcycling of polyolefin plastics27Photocatalysis as a tool for upcycling of polymers13Organic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer32A General Approach for Photo‐Oxidative Degradation of Various Polymers16Photocatalytic upcycling of plastics containing aliphatic C–C bonds into versatile chemicals9Challenges and Future Perspectives in Photocatalysis: Conclusions from an Interdisciplinary Workshop222Ozone‐Assisted Cu‐Based Catalysts for the Efficient Electro‐Reforming Glycerol to Formic Acid4FeCl3-Promoted Photocatalytic Cleavage of Cα–Cβ Bond in Lignin and Lignin Model to Benzoic Acid8Targeted valorization of waste polycarbonate into bisphenol A dimethyl ether8Selective Degradation of Polyethylene Terephthalate Plastic Waste Using Iron Salt Photocatalysts15Degradation of stable thermosetting epoxy resins mediated by bases in amide solvents18The carbonate exchange reaction strategy for chemical recycling of poly(bisphenol A carbonate) into an epoxy-curing agent8Recent Progress for Designing of Catalysts for Photothermal Conversion of Plastic Wastes48Research progress and challenges in the upcycling of polyolefin plastics through chemical oxidation4Catalysis in sustainable energy resources: overview studies of hydrogen, methane, biomass and plastics21Controllable site-selective C–C bond cleavage for the divergent synthesis of imidazo[1,5- a ]pyridine derivatives0Photoredox Catalysis0Reaction development: a student's checklist15Synthesis of Polyamides Bearing Directing Groups and Their Catalytic Depolymerization3Photocatalytic Upgrading of Plastic Waste into High-Value-Added Chemicals and Fuels: Advances and Perspectives49ZnTi layered double hydroxide/dealkaline lignin 2D/2D nanosheets for ultraviolet shielding poly(ethylene terephthalate) nanocomposites2On the role of bacterial gut microbiota from supralittoral amphipod Talitrus saltator (Montagu, 1808) in bioplastic degradation1Polymer Chain Modification via HAT Chemistry and Its Application in Graft Copolymer Synthesis13A Mind Map to Address the Next Generation of Artificial Photosynthesis Experiments3In Situ Modification Assisted by HAT Chemistry for the Main Chain Initiated Depolymerization of Polymethacrylates18Light-Driven C(sp3)–C(sp3) Bond Functionalizations Enabled by the PCET Activation of Alcohol O–H Bonds27A Light‐Driven Closed‐Loop Chemical Recycling System for Polypinacols3Recent advances in catalytic hydroprocessing of lignin and plastics for aromatic compound production13Bioinspired Dual-Stimulus-Responsive Macromolecular Engineering Enables Chemically Recyclable, High-Performance and Fire-Retardant Plastic2Surface metal reconstruction enables stable in-situ embedding of active nanostructures on steel mesh for efficient, scalable pollutant degradation0Oxidative depolymerization of polyethylene (PE), polypropylene (PP) and polystyrene (PS) wastes to value-added chemicals8Progress in selective depolymerization of epoxy resin for sustainable recycling of carbon fiber reinforced epoxy resin composites13The photocatalytic synthesis and closed-loop recycling of poly(semi-aromatic 1,2-ethanediol)s1The Effect of Aliphatic or Aromatic Substituents on the Synthesis and Properties of Polyurethanes From AB ‐Type Monomers3From Alkylarenes to α-Amino Acid Derivatives via C-Difunctionalization6Recent advances in photocatalytic plastic degradation and upcycling: Catalysts, experiments, and mechanisms9Selective bond cleavage strategies for chemical recycling of thermosets and their composites10Formalizing structure–property relationships of highly-oxidizing and weakly-reducing organic cyanoarene photocatalysts0Continuous flow Hantzsch ester–enabled photocatalytic valorization of lignin β-O-4 and epoxy resin models2Degradation of Anhydride‐Cured Epoxy Thermosetting Resins Promoted by Two‐Phase Water–Ionic Liquid Mixtures1Structure Elucidation and Total Synthesis of Granolides A–C: Ethyl‐branched Sesquiterpenes From the Tropical Frog Gephyromantis granulatus0A holistic remedy to the plastic era through a high–performance photocatalytic system0Chemical recycling of carbon fibre-reinforced bisphenol A-based epoxy-amine composite for fibre and monomer production: A review0Operando Nanocavity-Confined Raman Spectroscopy Uncovers a Drilling-Shearing Mechanism in Nanoplastic Photodegradation0Base‐Mediated Degradation of Epoxy Thermosets via Carbon–Nitrogen Bond Cleavage for the Recovery of Amine Agents0A Tert ‐Alkyl Terephthalate Derivative as a Universal Degradable Unit for Condensation Polymers0Photocatalytic Recovery of Aromatic Chemicals from Waste Plastics0Chemical Recycling of Waste Wind‐Turbine Blades Through Polymer Deconstruction and Upcycling0“Light activation for polymer circularity”—Chapter in “polymer circularity in sustainable energy”0

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