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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 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 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: Electrophilic Radicals01:02

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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 Reactivity: Nucleophilic Radicals01:16

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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...
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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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Related Experiment Video

Updated: Jul 16, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Controlled Radical Polymerization Initiated by Solvated Electrons.

Xun Li1, Zhaoyan Pan1, Yichen Xia1

  • 1College of Materials Science and Engineering, Nanjing Tech University, No. 30 Puzhu Road (S), Nanjing, Jiangsu Province, 211816, P.R. China.

Macromolecular Rapid Communications
|September 15, 2023
PubMed
Summary

Solvated electrons initiate polymerization, enabling controlled radical polymerization (CRP) with predictable polymer properties. This novel system offers unique control over polymerization through factors like sodium concentration and electric fields.

Keywords:
controlled radical polymerizationelectric-field effectone-electron transfer initiationsolvated-electron initiated polymerizationsolvent effect

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Solvated electrons (esol-) are potent reducing agents capable of initiating monomer polymerization via one-electron transfer.
  • Controlling polymerization processes is crucial for tailoring polymer properties such as molecular weight and distribution.
  • Existing controlled radical polymerization (CRP) techniques offer methods for polymer synthesis but may have limitations.

Purpose of the Study:

  • To investigate the use of solvated electrons generated from Na/hexamethylphosphoramide as an initiation system for polymerization.
  • To explore the influence of sodium concentration on polymerization mechanisms, specifically radical versus anionic initiation.
  • To demonstrate and characterize a novel controlled radical polymerization (CRP) system initiated by solvated electrons.

Main Methods:

  • Generation of solvated electron solutions using sodium in hexamethylphosphoramide at varying sodium concentrations.
  • Polymerization experiments to study monomer initiation and polymer growth.
  • Characterization of polymers using techniques to determine molecular weights and molecular weight distributions (e.g., Đ).

Main Results:

  • Sodium concentration dictates whether radical or anionic initiation occurs, with lower concentrations favoring radical pathways.
  • A controlled radical polymerization (CRP) was achieved at lower sodium concentrations, yielding polymers with predictable molecular weights and narrow distributions (lowest Đ = 1.25).
  • This CRP system exhibited unique behaviors, including solvent effects, electric field effects, and unusual copolymerization phenomena.

Conclusions:

  • A novel CRP system was developed using solvated electrons, offering a distinct method for polymer synthesis control.
  • The proposed mechanism involves a semi-conjugated radical with a negative charge, responsible for the observed controlled polymerization.
  • This research provides new insights into monomer initiation by solvated electrons and expands the toolkit for CRP.