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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...
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Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

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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: Overview01:11

Radical Reactivity: Overview

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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...
2.2K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.0K
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: Abstraction00:47

Radical Formation: Abstraction

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
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Updated: Sep 8, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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Aqueous electrochemically-triggered atom transfer radical polymerization.

Boyu Zhao1, Fred Pashley-Johnson1, Bryn A Jones1

  • 1University of Warwick UK p.wilson.1@warwick.ac.uk.

Chemical Science
|June 13, 2022
PubMed
Summary
This summary is machine-generated.

Simplified electrochemical atom transfer radical polymerization (seATRP) using a novel copper complex enables controlled polymer synthesis in water. This electrochemically-triggered process offers a new pathway for creating polymers with specific molecular weights.

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Area of Science:

  • Polymer Chemistry
  • Electrochemistry
  • Materials Science

Background:

  • Atom Transfer Radical Polymerization (ATRP) is a controlled polymerization technique.
  • Electrochemical ATRP (eATRP) offers a metal-free or reduced metal catalyst approach.
  • Copper complexes are commonly used catalysts in ATRP.

Purpose of the Study:

  • To report simplified electrochemical atom transfer radical polymerization (seATRP) for the first time.
  • To investigate the use of copper(II)-N-propyl pyridineimine complexes (Cu(II)(NPPI)2) in aqueous polymerization.
  • To elucidate the polymerization mechanism, distinguishing between electrochemically mediated and triggered processes.

Main Methods:

  • Utilized simplified electrochemical atom transfer radical polymerization (seATRP).
  • Employed copper(II)-N-propyl pyridineimine complexes (Cu(II)(NPPI)2) as catalysts.
  • Conducted polymerization in aqueous solution using oligo(ethylene glycol) methyl ether methacrylate (OEGMA) monomer under standard electrolysis conditions.

Main Results:

  • Achieved poly(oligo(ethylene glycol) methyl ether methacrylate) (POEGMA) with good control over molecular weight distribution (Đm < 1.35).
  • Observed continued monomer conversion after halting electrolysis, indicating incomplete electrochemical control.
  • Demonstrated that polymerization extent and rate depend on an initial electrolysis period.

Conclusions:

  • The seATRP using Cu(II)(NPPI)2 in aqueous solution provides controlled POEGMA synthesis.
  • The polymerization mechanism is proposed to be electrochemically-triggered rather than electrochemically mediated.
  • This finding differentiates the Cu(II)(NPPI)2 system from previously reported copper(II) ligand complexes in eATRP.