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

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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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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Radical Chain-Growth Polymerization: Chain Branching01:17

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Macrochain Transfer Agents for Catalytic Ring-Opening Metathesis Polymerization.

Indradip Mandal1, Ankita Mandal1, Andreas F M Kilbinger1

  • 1Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700 Fribourg, Switzerland.

ACS Macro Letters
|December 1, 2022
PubMed
Summary
This summary is machine-generated.

This study introduces polymer-based macrochain transfer agents for ring-opening metathesis polymerization. These agents enable efficient synthesis of well-defined polyethylene glycol (PEG) and polylactide (PLA) block copolymers.

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Area of Science:

  • Polymer Chemistry
  • Macromolecular Science
  • Catalysis

Background:

  • Ring-opening metathesis polymerization (ROMP) is a powerful tool for polymer synthesis.
  • Controlling polymer architecture and molecular weight distribution is crucial for advanced material applications.
  • Developing efficient macrochain transfer agents (MTAs) can simplify complex polymer synthesis.

Purpose of the Study:

  • To demonstrate the utility of a monosubstituted 1,3-diene polymer as a macrochain transfer agent (MTA) in ROMP.
  • To synthesize well-defined polyethylene glycol (PEG)- and polylactide (PLA)-based block copolymers.
  • To characterize the synthesized block copolymers and confirm their structures.

Main Methods:

  • Synthesis of PEG- and PLA-based macrochain transfer agents.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy, Size Exclusion Chromatography (SEC), and Matrix-Assisted Laser Desorption/Ionization-Time-of-Flight (MALDI-ToF) mass spectrometry.
  • Catalytic ring-opening metathesis polymerization in a one-pot approach.

Main Results:

  • Successful synthesis of PEG- and PLA-based macrochain transfer agents.
  • Preparation of poly(l-lactide) diblock, PEG-based diblock, and triblock (ABA type) copolymers with controlled chain lengths.
  • SEC analysis confirmed monomodal molecular weight distributions for the block copolymers.
  • DOSY NMR spectroscopy verified the block microstructures of the synthesized polymers.

Conclusions:

  • Monosubstituted 1,3-diene polymers effectively function as macrochain transfer agents in ROMP.
  • This method provides a versatile route to synthesize well-defined PEG and PLA block copolymers.
  • The developed approach offers a simplified and efficient pathway for creating advanced block copolymer architectures.