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Related Concept Videos

Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

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...
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

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 the...
Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...

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Related Experiment Video

Updated: May 25, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

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

Published on: April 22, 2016

Controlled radical polymerization mediated by amine-bis(phenolate) iron(III) complexes.

Laura E N Allan1, Jarret P MacDonald, Amy M Reckling

  • 1Department of Chemistry, University of Prince Edward Island, Charlottetown, PE, Canada.

Macromolecular Rapid Communications
|February 3, 2012
PubMed
Summary
This summary is machine-generated.

Iron(III) catalysts with chloro-substituted aromatic rings efficiently control radical polymerization, yielding polymers with low polydispersity. These catalysts offer fast polymerization rates and simple purification, making them highly effective for styrene and methyl methacrylate.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Published on: August 12, 2019

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Last Updated: May 25, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

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Published on: April 22, 2016

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Controlled radical polymerization (CRP) is crucial for synthesizing polymers with defined architectures.
  • Iron complexes offer a cost-effective and tunable alternative to traditional CRP catalysts.
  • Developing efficient and versatile iron-based catalysts remains an active area of research.

Purpose of the Study:

  • To investigate the catalytic activity of tetradentate amine-bis(phenolate) iron(III) halide complexes in controlled radical polymerization.
  • To evaluate the effect of aromatic ring substituents on catalyst performance.
  • To explore the polymerization kinetics and mechanism.

Main Methods:

  • Synthesis and characterization of iron(III) complexes with varying substituents.
  • Controlled radical polymerization of styrene and methyl methacrylate.
  • Analysis of polymer molecular weights and polydispersity indices (PDIs).
  • Kinetic studies to determine polymerization rates and mechanistic insights.

Main Results:

  • Iron(III) complexes with chloro-substituted aromatic rings demonstrated high efficiency in controlled radical polymerization.
  • Achieved low PDIs (as low as 1.11) and molecular weights consistent with theoretical predictions for styrene and methyl methacrylate.
  • Catalysts with alkyl substituents were less efficient.
  • Styrene polymerization exhibited one of the fastest rates reported to date, suggesting a multimechanism system.
  • Simple work-up procedures yielded pure white polymers despite colored polymerization media.

Conclusions:

  • Tetradentate amine-bis(phenolate) iron(III) halide complexes, particularly those with chloro substituents, are highly effective catalysts for controlled radical polymerization.
  • These catalysts provide excellent control over polymer molecular weight and PDI.
  • The findings highlight the potential of these iron complexes as efficient and practical catalysts for polymer synthesis.