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Related Concept Videos

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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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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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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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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Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from 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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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Programming Photodegradability into Vinylic Polymers via Radical Ring-Opening Polymerization.

Phuong T Do1,2, Berwyck L J Poad1,2,3, Hendrik Frisch1,2

  • 1School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, QLD-4000, Australia.

Angewandte Chemie (International Ed. in English)
|December 19, 2022
PubMed
Summary
This summary is machine-generated.

This study introduces a new method to make polymers degrade with light. By using coumarin and UVA light, researchers created cyclic polymers that break down quickly under UVB or sunlight.

Keywords:
CoumarinIon Mobility-Mass SpectrometryPhotodegradable PolymerRing-Opening PolymerizationSunlight Degradable Polymer

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Area of Science:

  • Polymer Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Photodegradable polymers offer remote control over degradation.
  • Existing synthetic methods for incorporating photodegradable units into polymers, particularly for radical polymerization, are limited.

Purpose of the Study:

  • To develop a novel strategy for programming photodegradability into vinylic polymers using wavelength-selective photocycloaddition.
  • To synthesize and characterize copolymers with light-responsive degradation properties.

Main Methods:

  • Utilized coumarin-terminated allylic sulfides and UVA light to initiate intramolecular [2+2] photocycloaddition, forming cyclic macromonomers.
  • Employed RAFT-mediated radical ring-opening polymerization (rROP) with methyl acrylate to create copolymers incorporating the photoreactive cyclic units.
  • Investigated polymer degradation triggered by UVB irradiation and natural sunlight.

Main Results:

  • Successfully synthesized cyclic macromonomers via UVA-induced photocycloaddition.
  • Developed copolymers containing photolabile coumarin dimers that exhibit wavelength-dependent degradation.
  • Achieved rapid polymer degradation (minutes) under UVB light and slower degradation (days) under sunlight exposure.

Conclusions:

  • The reported synthetic strategy enables the incorporation of photolabile linkages into vinylic polymers.
  • This method allows for tunable polymer degradation based on specific wavelengths of light.
  • The approach holds potential for developing advanced materials with controlled degradation properties.