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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: 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

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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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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Anionic Chain-Growth Polymerization: Mechanism01:04

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Electrochemically Mediated Atom Transfer Radical Polymerization Driven by Alternating Current.

Francesco De Bon1, Marco Fantin2, Vanessa A Pereira1

  • 1Centre for Mechanical Engineering, Materials and Processes (CEMMPRE), ARISE, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II, 3030-790, Coimbra, Portugal.

Angewandte Chemie (International Ed. in English)
|April 22, 2024
PubMed
Summary
This summary is machine-generated.

Alternating current (AC) electrolysis enhances electrochemically mediated Atom Transfer Radical Polymerization (eATRP) by regenerating copper activators. This method enables controlled polymerization of diverse monomers with high fidelity and robust electrodes.

Keywords:
ATRPalternating currentelectrochemistryligand designpolymerization

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Area of Science:

  • Electrochemistry
  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Alternating current (AC) and pulsed electrolysis offer advantages in electro(organic) synthesis.
  • Atom Transfer Radical Polymerization (ATRP) is a controlled polymerization technique.
  • Copper (Cu) complexes are common activators in ATRP.

Purpose of the Study:

  • To investigate the use of AC electrolysis in electrochemically mediated ATRP (eATRP).
  • To explore the dual regeneration of copper activators using AC electrolysis and chemical methods.
  • To assess the efficiency and scope of AC electrolysis in polymerizing various monomers.

Main Methods:

  • Employing sinusoidal, triangular, and square-wave AC electrolysis.
  • Utilizing Cu0 electrodes for activator regeneration and as a supplemental activator (SARA ATRP).
  • Testing AC electrolysis with diverse ATRP catalysts and eleven different monomers.

Main Results:

  • AC electrolysis facilitated faster and more controlled polymerization of acrylates compared to DC electrolysis or SARA ATRP alone.
  • Successful polymerization of eleven monomers in various media (water to bulk).
  • Effective polymerization across a range of catalyst activities, from low to high.
  • Chain extension experiments confirmed high chain-end fidelity for block copolymers.
  • Cu0 electrodes demonstrated robustness, supporting at least 15 consecutive polymerizations.

Conclusions:

  • AC electrolysis is a versatile and effective technique for eATRP.
  • The dual regeneration mechanism enhances polymerization control and efficiency.
  • This method offers broad applicability for diverse monomers and catalyst systems.
  • Robust Cu0 electrodes enable repetitive polymerization, highlighting practical utility.