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Related Concept Videos

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Base-Catalyzed Ring-Opening of Epoxides02:26

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Chemically Recyclable Polymer System Based on Nucleophilic Aromatic Ring-Opening Polymerization.

Yong-Liang Su1, Liang Yue2, Huan Tran3

  • 1School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Journal of the American Chemical Society
|June 12, 2023
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Summary
This summary is machine-generated.

Chemically recyclable polythioethers were developed using dynamic nucleophilic aromatic substitution chemistry. These novel polymers offer tunable properties and efficient depolymerization, advancing sustainable polymer science.

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Area of Science:

  • Polymer Science
  • Materials Chemistry
  • Sustainable Chemistry

Background:

  • Developing chemically recyclable polymers with desirable properties remains a significant challenge.
  • Reversible chemical reactions are crucial for efficient polymerization and depolymerization cycles.

Purpose of the Study:

  • To report a novel chemically recyclable polythioether system.
  • To demonstrate a well-defined monomer platform for chain-growth ring-opening polymerization via nucleophilic aromatic substitution (SNAr).

Main Methods:

  • Utilized dynamic nucleophilic aromatic substitution (SNAr) chemistry.
  • Employed readily accessible benzothiocane (BT) monomers for polymerization.
  • Investigated chain-growth ring-opening polymerization mechanism.

Main Results:

  • Achieved rapid polymerizations reaching completion in minutes.
  • Demonstrated easy customization of pendant functionalities for property tuning.
  • Obtained polythioether materials with performance comparable to commercial thermoplastics.
  • Successfully depolymerized polymers back to original monomers in high yields.

Conclusions:

  • The reported polythioether system is the first example of a well-defined monomer platform for SNAr chain-growth ring-opening polymerization.
  • This work provides a viable route towards sustainable polymers with tunable properties and efficient recyclability.