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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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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: 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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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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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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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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Alternating copolymerization by nitroxide-mediated polymerization and subsequent orthogonal functionalization.

Matthias Tesch1, Johannes A M Hepperle, Henning Klaasen

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster (Germany).

Angewandte Chemie (International Ed. in English)
|March 5, 2015
PubMed
Summary

Researchers developed a new method for creating functionalized alternating copolymers. This technique uses nitroxide-mediated polymerization and click chemistry to produce dual-functionalized polymers for diverse applications.

Keywords:
active estersalternating polymerizationnitroxide-mediated polymerizationorthogonal functionalizationthiol-ene reactions

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Alternating copolymers offer unique properties but their synthesis can be challenging.
  • Functionalization of polymers is key to tailoring material properties for specific applications.
  • Orthogonal reactions allow for selective modification of polymer chains.

Purpose of the Study:

  • To present a novel and efficient method for preparing functionalized alternating copolymers.
  • To demonstrate the versatility of the method through dual-functionalization.
  • To create a library of functionalized alternating copolymers for further research.

Main Methods:

  • Nitroxide-mediated polymerization of hexafluoroisopropyl acrylate and 7-octenyl vinyl ether.
  • Sequential application of orthogonal polymer-analogous reactions: thiol-ene click reaction followed by amidation.
  • Synthesis of a library of 15 functionalized alternating copolymer examples.

Main Results:

  • Successful synthesis of alternating copolymers via nitroxide-mediated polymerization.
  • Demonstration of dual-functionalization using orthogonal thiol-ene click and amidation reactions.
  • Generation of a diverse library of functionalized alternating copolymers.

Conclusions:

  • The presented method provides a facile route to dual-functionalized alternating copolymers.
  • The orthogonal functionalization strategy allows for precise control over polymer properties.
  • This approach expands the toolkit for designing advanced functional materials.