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Related Concept Videos

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
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 Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

3.9K
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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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

10.4K
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.
10.4K
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

3.8K
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...
3.8K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

4.5K
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...
4.5K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

3.0K
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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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Simplified electrochemically mediated atom transfer radical polymerization using a sacrificial anode.

Sangwoo Park1, Paweł Chmielarz, Armando Gennaro

  • 1Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, PA 15213 (USA).

Angewandte Chemie (International Ed. in English)
|January 8, 2015
PubMed
Summary

Simplified electrochemically mediated atom transfer radical polymerization (seATRP) uses a sacrificial anode for efficient polymer synthesis. This method allows control over polymerization rates and produces polymers with narrow molecular-weight distribution.

Keywords:
atom transfer radical polymerizationblock copolymerselectrochemistrysacrificial electrodes

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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 external control over polymerization kinetics.
  • Simplifying eATRP procedures is crucial for broader application.

Purpose of the Study:

  • To simplify the electrochemically mediated atom transfer radical polymerization (seATRP) process.
  • To investigate the effect of applied potentials on polymerization rate and control.
  • To develop galvanostatic conditions for seATRP.

Main Methods:

  • Utilized a sacrificial aluminum wire anode immersed directly in the reaction flask.
  • Performed seATRP under potentiostatic conditions with varying applied potentials (Eapp).
  • Developed a two-electrode system for galvanostatic seATRP.

Main Results:

  • Achieved efficient polymerization under both potentiostatic and galvanostatic conditions.
  • Demonstrated that more reducing potentials (lower Eapp) led to faster polymerization rates (Rp).
  • Synthesized high-molecular-weight poly(butyl acrylate) (PBA) and diblock copolymers with >90% conversion and narrow molecular-weight distribution.

Conclusions:

  • seATRP provides an efficient and simplified method for controlled polymerization.
  • Polymerization rate is tunable by adjusting applied potentials.
  • The developed seATRP method is suitable for synthesizing polymers and copolymers with controlled characteristics.