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

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

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...

Free-Radical Chain Reaction and Polymerization of Alkenes

Free-Radical Chain Reaction and Polymerization of Alkenes

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.

Radical Chain-Growth Polymerization: Overview

Radical Chain-Growth Polymerization: Overview

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...

Olefin Metathesis Polymerization: Overview

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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...

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 species into the...

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

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Related Experiment Video

Updated: May 7, 2026

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

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

Published on: November 21, 2017

Degradable and comb-like PEG-based copolymers by nitroxide-mediated radical ring-opening polymerization.

Vianney Delplace¹, Antoine Tardy, Simon Harrisson

¹Institut Galien Paris-Sud, UMR CNRS 8612, University Paris-Sud , Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry Cedex, France.

Biomacromolecules

|September 17, 2013

Summary

Researchers developed degradable PEG-based copolymers using nitroxide-mediated polymerization. The cyclic ketene acetal MPDL yielded well-defined, non-cytotoxic materials ideal for biomedical applications like PEGylation.

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Last Updated: May 7, 2026

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

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Published on: November 21, 2017

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Area of Science:

Polymer Chemistry
Biomedical Engineering
Materials Science

Background:

Developing degradable polymers is crucial for biomedical applications.
Poly(ethylene glycol) (PEG)-based copolymers offer biocompatibility.
Controlled polymerization techniques are needed for precise polymer synthesis.

Purpose of the Study:

To synthesize novel degradable PEG-based copolymers.
To explore the use of cyclic ketene acetals in copolymerization.
To evaluate the properties and applications of the resulting copolymers for biomedical use.

Main Methods:

Copolymerization of cyclic ketene acetals (MDO, BMDO, MPDL) with PEG-methacrylate and acrylonitrile/styrene.
Utilized nitroxide-mediated radical ring-opening polymerization at 90 °C.
Assessed hydrolytic degradation and non-cytotoxicity on cell lines.

Main Results:

MPDL demonstrated superior performance, achieving high monomer conversions.
Well-defined PEG-based copolymers with tunable ester content were synthesized.
Copolymers exhibited nearly complete hydrolytic degradation and were non-cytotoxic to fibroblasts, endothelial cells, and macrophages.

Conclusions:

MPDL is a promising monomer for creating degradable PEG-based copolymers.
The synthesized copolymers are suitable for biomedical applications, including PEGylation and bioconjugation.
Nitroxide-mediated polymerization offers a viable route for designing advanced biomaterials.