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Related Concept Videos

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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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...
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Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Base-Catalyzed Ring-Opening of Epoxides02:26

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

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

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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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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

2.1K
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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Updated: Sep 9, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Ion-Exchange Catalyst Marries Cationic Ring-Opening Polymerization with Functional Carboxylic Acid Initiators.

Tingwei Chen1, Chenke Zhao1, Junpeng Zhao1,2

  • 1Faculty of Materials Science and Engineering, South China University of Technology, Guangzhou 510640, China.

Journal of the American Chemical Society
|September 4, 2025
PubMed
Summary
This summary is machine-generated.

Carboxylic acids can now initiate cationic ring-opening polymerization for functional polymers using a novel catalyst system. This breakthrough enables controlled synthesis of polymers with desired end-group functionalities.

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Area of Science:

  • Polymer Chemistry
  • Macromolecular Engineering
  • Organic Synthesis

Background:

  • Conventional cationic polymerization initiators (strong acids/electrophiles) lack functional group compatibility.
  • Carboxylic acids are functional-group tolerant but historically incapable of initiating cationic polymerization.
  • One-step synthesis of end-functionalized polymers remains a challenge.

Purpose of the Study:

  • To develop a novel method for carboxylic acid-initiated cationic ring-opening polymerization (CROP).
  • To enable the one-step synthesis of end-functionalized polymers with controlled architectures.
  • To explore the mechanism and scope of this new polymerization technique.

Main Methods:

  • Carboxylic acid-initiated CROP of 2-ethyl-2-oxazoline (EtOx) using lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) as a catalyst.
  • Investigation of the role of Li+ -carboxylate interaction and anion exchange dynamics.
  • Exploration of solvent effects (γ-valerolactone) on polymerization.
  • Characterization of polymer properties including molar mass, dispersity, and end-group fidelity.
  • Computational studies to elucidate reaction mechanisms.

Main Results:

  • Successful initiation of EtOx CROP by carboxylic acids, enabled by LiTFSI catalyst.
  • Demonstrated control over molar mass, low dispersity, and high end-group fidelity.
  • Polymerization rate influenced by initiator structure and solvent.
  • Achieved functional polyEtOx with properties like protein resistance and aggregation-induced emission.

Conclusions:

  • A new catalytic paradigm for weak-acid-initiated CROP has been established.
  • This method overcomes limitations of traditional initiators, expanding polymer synthesis capabilities.
  • The developed technique offers a versatile platform for macromolecular engineering and creating functional materials.