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Related Concept Videos

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

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

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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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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.0K
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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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.8K
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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Preparation of Epoxides03:00

Preparation of Epoxides

8.1K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

8.1K
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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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Orthogonally deconstructable and depolymerizable polysilylethers via entropy-driven ring-opening metathesis

Alayna M Johnson1, Keith E L Husted1, Landon J Kilgallon1

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA. jaj2109@mit.edu.

Chemical Communications (Cambridge, England)
|July 12, 2022
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Researchers developed new deconstructable polysilylethers using entropy-driven ring-opening metathesis polymerization. These polymers exhibit low glass transition temperatures and can be rapidly broken down using specific triggers.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Ring-opening metathesis polymerization (ROMP) is a versatile method for polymer synthesis.
  • Developing polymers with tunable properties and controlled degradation is crucial for advanced applications.
  • Cyclic silyl ether monomers offer unique structural possibilities for polymer design.

Purpose of the Study:

  • To synthesize novel polysilylethers utilizing entropy-driven ring-opening metathesis polymerization (ED-ROMP).
  • To investigate the thermal properties, deconstructability, and microstructure of the synthesized polymers.
  • To explore the potential applications of this new class of deconstructable polymers.

Main Methods:

  • Entropy-driven ring-opening metathesis polymerization (ED-ROMP) of cyclic bifunctional silyl ether-based monomers.
  • Characterization of polymer thermal stability and glass transition temperature (Tg).
  • Investigation of deconstruction mechanisms using acid, fluoride, and metathesis catalysts.

Main Results:

  • Successful synthesis of novel polysilylethers with good thermal stability.
  • Achieved ultra-low glass transition temperature (Tg) of -88 °C.
  • Demonstrated rapid deconstruction via silicon-oxygen bond cleavage and partial depolymerization.

Conclusions:

  • ED-ROMP provides a new route to polysilylethers with desirable properties.
  • The synthesized polymers are rapidly deconstructable, offering environmental and recycling advantages.
  • The regiorandom nature of the ED-ROMP process was elucidated, providing insights into polymer microstructure.