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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

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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 of a...
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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.
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

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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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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Metal-free ring-opening metathesis polymerization.

Kelli A Ogawa1, Adam E Goetz, Andrew J Boydston

  • 1Department of Chemistry, University of Washington , Seattle, Washington 98195, United States.

Journal of the American Chemical Society
|January 10, 2015
PubMed
Summary

This study introduces a novel metal-free ring-opening metathesis polymerization (ROMP) method. Organic initiators are oxidized to create radical cations, enabling controlled polymerization without transition metals.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Ring-opening metathesis polymerization (ROMP) traditionally relies on transition metal catalysts.
  • Developing metal-free polymerization methods is crucial for sustainability and avoiding metal contamination in products.

Purpose of the Study:

  • To establish a novel, metal-free approach for controlled ROMP.
  • To demonstrate the efficacy of organic initiator oxidation for ROMP.
  • To achieve temporal control over polymerization using photoredox catalysis.

Main Methods:

  • Generation of radical cations via one-electron oxidation of vinyl ethers using an organic photoredox mediator.
  • Reaction of generated radical cations with norbornene to initiate ROMP.
  • Utilizing on/off cycles of light exposure for temporal control of polymer growth.

Main Results:

  • Achieved ROMP with microstructures identical to metal-mediated ROMP.
  • Obtained high polymer yields under mild reaction conditions.
  • Demonstrated good correlation between molecular weight and monomer-to-catalyst ratios.
  • Showcased temporal control over polymerization reinitiation via light exposure.

Conclusions:

  • This work presents the first metal-free method for controlled ROMP.
  • The developed method offers a sustainable and efficient alternative to traditional metal-mediated ROMP.
  • Photoredox-mediated oxidation of organic initiators provides a versatile platform for controlled polymerization.