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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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

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

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...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

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Thiol- and Disulfide-Functionalized Polycyclooctene: Metathesis Polymerization, Degradation, and Reformation.

Kyoungwon Lee1, Hong-Gyu Seong1, Thomas P Russell1,2

  • 1Polymer Science & Engineering Department, Conte Center for Polymer Research, University of Massachusetts, Amherst, Massachusetts 01003, United States.

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|May 2, 2025
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Summary

Researchers developed degradable polyolefins by incorporating disulfide bonds. This innovation allows for controlled polymer deconstruction and reconstruction, offering a promising solution for plastic waste management and recyclable materials.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Sustainable Chemistry

Background:

  • Global plastic waste is a significant environmental challenge due to high production and inefficient recycling.
  • Developing polymers with built-in degradability and recyclability is crucial for sustainability.

Purpose of the Study:

  • To design and synthesize degradable polyolefins with controlled deconstruction and reconstruction capabilities.
  • To explore the use of disulfide-containing polymers for recyclable materials.

Main Methods:

  • Synthesis of telechelic α,ω-dithiopolycyclooctene (PCOE) via ring-opening metathesis polymerization.
  • Controlled oxidation to form disulfide linkages and subsequent reductive degradation.
  • Oxidative repolymerization to reform the polymer structure.

Main Results:

  • Successfully synthesized disulfide-containing PCOE with controllable oxidation degrees.
  • Demonstrated efficient reductive degradation and oxidative repolymerization of the synthesized polymers.
  • Achieved integration of degradable and reformable moieties into metathesis-derived polymers.

Conclusions:

  • The developed approach enables the creation of degradable and reformable unsaturated polyolefins.
  • This method offers a pathway to soluble, processable polymers with integrated dynamic covalent chemistry.
  • The findings contribute to the development of advanced recyclable materials for reduced plastic waste.