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Radical Chain-Growth Polymerization: Overview01:10

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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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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 species into...
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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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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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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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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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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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Photoinduced Organocatalyzed Atom Transfer Radical Polymerization Using Continuous Flow.

Bonnie L Ramsey1, Ryan M Pearson1, Logan R Beck1

  • 1Department of Chemistry and Biochemistry University of Colorado Boulder, Boulder, Colorado 80309, United States.

Macromolecules
|October 21, 2017
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Summary

Metal-free organocatalyzed atom transfer radical polymerization (O-ATRP) is now adaptable to continuous flow systems. This advancement offers enhanced polymerization performance, achieving narrow molecular weight distributions and high initiator efficiencies with minimal photocatalyst.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Photocatalysis

Background:

  • Atom transfer radical polymerization (ATRP) traditionally relies on transition metals.
  • Organocatalyzed ATRP (O-ATRP) offers a metal-free alternative using organic photoredox catalysts.
  • Previous O-ATRP studies were limited to batch reaction formats.

Purpose of the Study:

  • To adapt organocatalyzed atom transfer radical polymerization (O-ATRP) to a continuous flow system.
  • To investigate the polymerization performance under continuous flow conditions.
  • To demonstrate the robustness and versatility of flow O-ATRP.

Main Methods:

  • Utilized visible-light absorbing organic photoredox catalysts for O-ATRP.
  • Implemented a continuous flow reactor setup for the polymerization.
  • Tested a diverse range of methacrylate monomers.
  • Performed chain-extension polymerizations to assess versatility.

Main Results:

  • Achieved narrow molecular weight distributions (as low as 1.05).
  • Demonstrated quantitative initiator efficiencies.
  • Successfully employed low photocatalyst loadings (0.01%).
  • Showcased versatility with various methacrylate monomers and chain extensions.

Conclusions:

  • Continuous flow O-ATRP is a robust and versatile polymerization method.
  • Flow conditions enhance polymerization performance compared to batch methods.
  • This metal-free approach offers efficient and controlled polymer synthesis.