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Related Concept Videos

Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

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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

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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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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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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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Step-Growth Polymerization: Overview01:03

Step-Growth Polymerization: Overview

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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Mechanism-Guided Design of Chain-Growth Click Polymerization Based on a Thiol-Michael Reaction.

Suqiu Jiang1, Hanchu Huang1

  • 1School of Materials Science and Engineering, Sun Yat-Sen University, Guangzhou, 510006, China.

Angewandte Chemie (International Ed. in English)
|February 3, 2023
PubMed
Summary

This study introduces a new chain-growth click polymerization using the thiol-Michael reaction. This method efficiently synthesizes sulfur-containing polymers under ambient conditions, controllable with UV light.

Keywords:
Allylic SulfideChain-Growth PolymerizationClick PolymerizationRing-Opening PolymerizationThiol-Michael Reaction

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Chain-growth polymerization offers precise control over polymer architecture.
  • Click polymerization enables efficient and selective bond formation.
  • Developing new chain-growth click polymerization methods is crucial for advanced polymer synthesis.

Purpose of the Study:

  • To report a novel chain-growth click polymerization strategy.
  • To utilize the thiol-Michael reaction for controlled polymer synthesis.
  • To enable spatiotemporal control over polymerization using UV light.

Main Methods:

  • Employing thiol-Michael addition for chain-growth polymerization.
  • Utilizing ultraviolet (UV) light for spatiotemporal control.
  • Conducting density functional theory (DFT) calculations to understand reaction mechanisms.

Main Results:

  • Achieved efficient synthesis of sulfur-containing polymers.
  • Obtained polymers with excellent yields and high molecular weights.
  • Identified thiolate addition to Michael acceptor as rate-determining step.
  • Demonstrated that phenyl group introduction facilitates chain-growth.

Conclusions:

  • Developed a novel UV-light-regulated chain-growth click polymerization.
  • The thiol-Michael reaction provides an efficient route to functional polymers.
  • This method offers a unique approach for creating advanced sulfur-containing polymers.