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Related Concept Videos

Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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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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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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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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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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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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Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

2.7K
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

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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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Polymer Classification: Stereospecificity01:26

Polymer Classification: Stereospecificity

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Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
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Updated: Aug 28, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Mechanochemical solid-state vinyl polymerization with anionic initiator.

Kwangho Yoo1,2, Gue Seon Lee1, Hyo Won Lee1

  • 1Department of Chemistry, Research Institute of Physics and Chemistry, Jeonbuk National University, Jeonju 54896, Republic of Korea. jeunggonkim@jbnu.ac.kr.

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|September 20, 2022
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Summary
This summary is machine-generated.

Mechanochemistry enables efficient polymer synthesis. However, mechanochemical anionic polymerization unexpectedly involves radical processes during chain propagation, differing from conventional methods.

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Area of Science:

  • Polymer Chemistry
  • Mechanochemistry
  • Organic Synthesis

Background:

  • Mechanochemistry offers efficient, green, and novel polymer synthesis routes.
  • While mechanochemistry has been applied to polymer synthesis, fundamental reactions like anionic polymerization remain underexplored.
  • Anionic polymerization of vinyl compounds has been investigated under mechanochemical conditions.

Purpose of the Study:

  • To explore the mechanochemical anionic polymerization of methacrylate and styrenic monomers.
  • To investigate the mechanism and efficiency of solid-state anionic polymerization induced by high-speed ball-milling.
  • To determine if conventional anionic polymerization features like molecular weight control are achievable under mechanochemical conditions.

Main Methods:

  • Solid-state polymerization of 4-biphenyl methacrylate and 4-vinyl biphenyl using secondary butyl lithium under high-speed ball-milling.
  • Exclusion of radical initiation pathways to isolate the anionic polymerization process.
  • Analysis of milling parameters, in-situ reaction monitoring, and microstructural characterization of the resulting polymers.

Main Results:

  • Successful polymerization of both monomers was achieved with good efficiency, initiated by alkyl anions.
  • Conventional anionic polymerization characteristics, such as controlled molecular weight and narrow dispersity, were not observed.
  • Mechanochemical analysis revealed a deviation from standard anionic polymerization mechanisms.

Conclusions:

  • The mechanochemical process involves a hybrid mechanism where anionic initiation is followed by radical propagation.
  • Mechanical forces fracture polymer chains, generating macroradicals that contribute to the polymerization process.
  • The study highlights the unique mechanistic pathways in mechanochemical polymerization, distinct from traditional solution-based methods.