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Related Concept Videos

Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

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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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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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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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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Radical Formation: Addition00:47

Radical Formation: Addition

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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Metal-free atom transfer radical polymerization.

Nicolas J Treat1, Hazel Sprafke, John W Kramer

  • 1Materials Department, Materials Research Laboratory, University of California , Santa Barbara, California 93106, United States.

Journal of the American Chemical Society
|November 1, 2014
PubMed
Summary
This summary is machine-generated.

This study introduces a metal-free atom transfer radical polymerization (ATRP) method using light and organic photoredox catalysts. This approach offers excellent control over polymer properties and enables versatile block copolymer synthesis.

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Area of Science:

  • Polymer Chemistry
  • Organic Catalysis
  • Photochemistry

Background:

  • Traditional atom transfer radical polymerization (ATRP) methods often suffer from metal contamination.
  • Developing metal-free polymerization techniques is crucial for applications requiring high purity.

Purpose of the Study:

  • To report a novel metal-free ATRP process utilizing light and organic photoredox catalysts.
  • To demonstrate efficient control over polymer molecular weight, polydispersity, and chain ends.
  • To showcase the facile synthesis of block copolymers and integration with other controlled radical processes.

Main Methods:

  • Employing visible light to mediate polymerization.
  • Utilizing organic-based photoredox catalysts for activation and deactivation cycles.
  • Investigating the polymerization of vinyl monomers.

Main Results:

  • Achieved efficient polymerization of vinyl monomers with excellent control.
  • Demonstrated precise control over molecular weight, polydispersity, and chain ends.
  • Facilitated straightforward synthesis of block copolymers with high structural versatility.

Conclusions:

  • The developed metal-free ATRP system overcomes metal contamination issues.
  • Organic photoredox catalysts offer a versatile platform for controlled radical polymerization.
  • This methodology holds promise for advanced polymer synthesis and small molecule chemistry.