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Related Concept Videos

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...
2.6K
Olefin Metathesis Polymerization: Overview01:13

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...
2.2K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

1.9K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
1.9K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.4K
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...
2.4K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.7K
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...
8.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Related Experiment Video

Updated: Jul 24, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Carbodiimide Ring-Opening Metathesis Polymerization.

J Drake Johnson1, Samuel W Kaplan1, Jozsef Toth1

  • 1Department of Chemistry, University of North Carolina at Chapel Hill; Chapel Hill, North Carolina 27599, United States.

ACS Central Science
|July 3, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for creating nitrogen-rich polymers, overcoming a major challenge in materials science. This breakthrough allows for precise synthesis of advanced macromolecules with potential applications in various fields.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Area of Science:

  • Polymer Chemistry
  • Macromolecular Science
  • Organic Synthesis

Background:

  • Controlled nitrogen incorporation into polymer backbones is a significant challenge, limiting the development of advanced soft materials.
  • Existing nitrogen-rich polymers are scarce and often lack synthetic precision, hindering structure-property relationship studies.
  • Nature's proteins demonstrate high functionality achievable through nitrogen-rich structures, a benchmark for synthetic materials.

Purpose of the Study:

  • To develop a precise and scalable method for synthesizing nitrogen-rich macromolecules.
  • To explore the potential of ring-opening metathesis polymerization (ROMP) for carbodiimide monomers.
  • To enable the creation of diverse polymer architectures, including polyureas, polythioureas, and polyguanidinates.

Main Methods:

  • Mechanistic discovery of carbodiimide ring-opening metathesis polymerization (ROMP).
  • Initiation and catalysis of ROMP using a novel iridium guanidinate complex.
  • Derivatization of resulting polycarbodiimides via nucleophilic addition.

Main Results:

  • Successful ROMP of N-aryl and N-alkyl cyclic carbodiimides was achieved.
  • A versatile strategy for preparing polyureas, polythioureas, and polyguanidinates with controlled architectures was established.
  • The developed method offers a scalable approach to nitrogen-rich polymers.

Conclusions:

  • This work presents a significant advancement in metathesis chemistry, enabling precise synthesis of nitrogen-rich polymers.
  • The findings open new avenues for investigating structure-folding-property relationships in complex macromolecules.
  • The developed methodology facilitates the creation of novel soft materials with tunable properties.