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Related Concept Videos

Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

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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: Mechanism01:09

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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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Radical Reactivity: Overview01:11

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Formation: Homolysis00:54

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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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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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Organocatalyzed atom transfer radical polymerization driven by visible light.

Jordan C Theriot1, Chern-Hooi Lim2, Haishen Yang1

  • 1Department of Chemistry and Biochemistry, University of Colorado Boulder, Boulder, CO 80309, USA.

Science (New York, N.Y.)
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Summary

Researchers developed new organic photoredox catalysts for atom transfer radical polymerization (ATRP). These catalysts enable precise polymer synthesis with visible light, avoiding metal contamination and achieving tunable molecular weights.

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Area of Science:

  • Polymer Chemistry
  • Organic Catalysis
  • Photoredox Catalysis

Background:

  • Atom transfer radical polymerization (ATRP) is a widely used polymer synthesis method offering excellent control over polymer properties.
  • A significant limitation of metal-catalyzed ATRP is the residual metal contamination in the final polymer product.
  • Existing organic photoredox catalysts for ATRP have not matched the performance of metal-based systems.

Purpose of the Study:

  • To develop metal-free photoredox catalysts for ATRP that overcome the limitations of current methods.
  • To achieve high initiator efficiencies and precise control over polymer synthesis using visible light activation.
  • To introduce a new class of organic photoredox catalysts for controlled polymerization.

Main Methods:

  • Computationally directed discovery was employed to identify novel catalyst candidates.
  • Diaryl dihydrophenazines were synthesized and characterized as strongly reducing photoredox catalysts.
  • Visible light was used to activate the catalysts for atom transfer radical polymerization.

Main Results:

  • The newly developed diaryl dihydrophenazine catalysts demonstrated high initiator efficiencies.
  • Visible light activation enabled the synthesis of polymers with tunable molecular weights.
  • Polymers with low dispersities were obtained, indicating precise control over the polymerization process.
  • The catalysts effectively mediated ATRP without metal contamination.

Conclusions:

  • Diaryl dihydrophenazines represent a promising class of organic photoredox catalysts for metal-free ATRP.
  • These catalysts offer a viable alternative to metal-based systems, addressing concerns about contamination.
  • The findings open new avenues for controlled polymer synthesis using sustainable and efficient photoredox catalysis.