Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of Epoxides03:00

Preparation of Epoxides

7.7K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
7.7K
Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

8.5K
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.
8.5K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.0K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.0K
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

2.8K
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...
2.8K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.2K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.2K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

1.7K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
1.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Synthesis and Morphology of High-Molecular-Weight Polyisobutylene-Polystyrene Block Copolymers Containing Dynamic Covalent Bonds.

Macromolecular rapid communications·2022
Same author

Responsive and Degradable Highly Branched Polymers with Hypervalent Iodine(III) Groups at the Branching Points.

Macromolecular rapid communications·2019
Same author

Hypervalent Iodine Compounds with Tetrazole Ligands.

The Journal of organic chemistry·2018
Same author

Cationic branched polymers for cellular delivery of negatively charged cargo.

Journal of drug delivery science and technology·2018
Same author

Iodosylbenzene-Pseudohalide-Based Initiators for Radical Polymerization.

The Journal of organic chemistry·2017
Same author

Reversible Deactivation Radical Polymerization of Monomers Containing Activated Aziridine Groups.

Macromolecular rapid communications·2016

Related Experiment Video

Updated: May 6, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

10.5K

Epoxides as reducing agents for low-catalyst-concentration atom transfer radical polymerization.

Shannon R Woodruff1, Brad J Davis1, Nicolay V Tsarevsky1

  • 1Department of Chemistry and Center for Drug Discovery, Design, and Delivery in Dedman College, Southern Methodist University, 3215 Daniel Avenue, Dallas, TX, 75275, USA.

Macromolecular Rapid Communications
|November 12, 2013
PubMed
Summary

Activators regenerated via electron transfer atom transfer radical polymerization (ARGET ATRP) prepare well-defined polymers without external reducing agents. Epoxide groups intrinsically reduce catalyst complexes, enabling controlled polymerization and block copolymer synthesis.

Keywords:
atom transfer radical polymerization (ATRP)block copolymerscatalysiscontrolled radical polymerizationepoxides

More Related Videos

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

7.4K
Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

3.2K

Related Experiment Videos

Last Updated: May 6, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

10.5K
Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

7.4K
Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

3.2K

Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Controlled radical polymerization techniques like ATRP are crucial for synthesizing polymers with defined architectures.
  • Traditional ATRP often requires high catalyst concentrations or external reducing agents, posing limitations for practical applications.
  • Developing self-regenerating catalytic systems is key to advancing sustainable polymerization methods.

Purpose of the Study:

  • To investigate the use of intrinsic epoxide groups as reducing agents for catalyst regeneration in ARGET ATRP.
  • To synthesize well-defined poly(glycidyl methacrylate) without external reducing agents.
  • To explore the formation of block copolymers through chain extension using this novel ARGET ATRP system.

Main Methods:

  • Utilizing electron transfer atom transfer radical polymerization (ARGET ATRP) with low catalyst concentrations.
  • Employing glycidyl methacrylate (GMA) as both monomer and intrinsic reducing agent.
  • Performing chain extension experiments with methyl methacrylate and methyl acrylate.

Main Results:

  • Successfully synthesized well-defined poly(glycidyl methacrylate) without external reducing agents.
  • Demonstrated the living nature of the polymerization through successful chain extensions.
  • Produced block copolymers by extending poly(glycidyl methacrylate) chains.
  • Showcased the ability of epoxide groups to continuously regenerate the Cu(I) activator from Cu(II) complexes.

Conclusions:

  • The epoxide groups in GMA serve as effective intrinsic reducing agents for catalyst regeneration in ARGET ATRP.
  • This method allows for the controlled synthesis of well-defined polymers and block copolymers under mild conditions.
  • The study highlights a sustainable approach to controlled polymerization by eliminating the need for external reducing agents.