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Chemically Recyclable Polymer System Based on Nucleophilic Aromatic Ring-Opening Polymerization

Yong-Liang Su, Liang Yue, Tran Doan Huan, Mizhi Xu, Anthony Engler, Rampi Ramprasad, H. Jerry Qi, Will R. Gutekunst

2023Journal of the American Chemical Society62 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide The development of chemically recyclable polymers with desirable properties is a long-standing but challenging goal in polymer science. Central to this challenge is the need for reversible chemical reactions that can equilibrate at rapid rates and provide efficient polymerization and depolymerization cycles. Based on the dynamic chemistry of nucleophilic aromatic substitution (S N Ar), we report a chemically recyclable polythioether system derived from readily accessible benzothiocane ( BT ) monomers. This system represents the first example of a well-defined monomer platform capable of chain-growth ring-opening polymerization through an S N Ar manifold. The polymerizations reach completion in minutes, and the pendant functionalities are easily customized to tune material properties or render the polymers amenable to further functionalization. The resulting polythioether materials exhibit comparable performance to commercial thermoplastics and can be depolymerized to the original monomers in high yields.

Topics & Concepts

Nucleophilic aromatic substitutionChemistryMonomerPolymerizationDepolymerizationPolymerPolymer chemistryRing-opening polymerizationNucleophileNucleophilic substitutionOrganic chemistryCatalysisAdvanced Polymer Synthesis and Characterizationbiodegradable polymer synthesis and propertiesSynthetic Organic Chemistry Methods
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