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4-Hydroxyproline-Derived Sustainable Polythioesters: Controlled Ring-Opening Polymerization, Complete Recyclability,

Jingsong Yuan1, Wei Xiong1, Xuhao Zhou1

  • 1Beijing National Laboratory for Molecular Sciences, Center for Soft Matter Science and Engineering, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , People's Republic of China.

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Chemically recyclable polythioesters (PTEs) were synthesized from biosourced materials. These novel polymers offer a sustainable solution for plastic waste, enabling efficient monomer recycling under mild conditions.

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Area of Science:

  • Polymer Chemistry
  • Sustainable Materials Science
  • Organic Synthesis

Background:

  • Petroleum-based plastics pose significant environmental and energy challenges.
  • There is a critical need for novel, chemically recyclable polymer alternatives.
  • Current recycling methods often fall short of addressing the full lifecycle of plastics.

Purpose of the Study:

  • To introduce a new class of biosourced polythioesters (PTEs) with high polymerizability and chemical recyclability.
  • To develop an economical and environmentally benign process for polymer synthesis and monomer recovery.
  • To explore the potential of these PTEs for high-value material applications.

Main Methods:

  • Synthesis of strained thiolactone monomers from 4-hydroxyproline.
  • Controlled ring-opening polymerization (ROP) using weak bases.
  • Copolymerization and side-chain functionalization for property tuning.
  • Selective depolymerization in dilute solution at ambient to moderate temperatures.
  • Density functional theory (DFT) for mechanistic insights.

Main Results:

  • Achieved high molar masses (up to 259 kg mol⁻¹) and narrow dispersities (below 1.15) for PTEs.
  • Demonstrated tunable polymer properties through copolymerization and functionalization.
  • Successfully recycled clean monomers from PTEs under mild conditions.
  • DFT calculations provided insights into the ROP/depolymerization mechanism.

Conclusions:

  • Biosourced PTEs offer a sustainable and versatile platform for polymer development.
  • The unique ROP and depolymerization chemistry enables efficient monomer recycling.
  • These PTEs hold promise for applications in optical plastics, self-immolative polymers, and biomaterials.