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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 of a...
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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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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

3.8K
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
3.8K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.0K
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.
12.0K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.7K
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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Related Experiment Video

Updated: Jan 3, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Living β-selective cyclopolymerization using Ru dithiolate catalysts.

Kijung Jung1, Tonia S Ahmed2, Jaeho Lee1

  • 1Department of Chemistry , Seoul National University , Seoul 08826 , Republic of Korea .

Chemical Science
|November 26, 2019
PubMed
Summary
This summary is machine-generated.

Researchers achieved living β-selective cyclopolymerization (CP) of conjugated polyenes by engineering steric factors in monomers or catalysts. This method allows controlled molecular weight and dispersity, enabling the synthesis of block copolymers.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Cyclopolymerization (CP) of 1,6-heptadiyne derivatives yields conjugated polyenes with five- or six-membered rings via α- or β-addition.
  • Previous ruthenium (Ru)-based catalysts favored α-addition, limiting access to six-membered ring structures.
  • Recent advancements achieved β-selective control but suffered from slow initiation and poor catalyst stability, hindering controlled polymerization.

Purpose of the Study:

  • To develop a living β-selective cyclopolymerization method for synthesizing conjugated polyenes with six-membered rings.
  • To achieve controlled polymerization by addressing issues of slow initiation and catalyst instability.
  • To enable the synthesis of well-defined block copolymers using a broad range of monomers.

Main Methods:

  • Rational engineering of steric factors in either the monomer or the ruthenium-based catalyst structure.
  • Utilizing dithiolate-chelated Ru catalysts for β-selective addition.
  • Employing in situ kinetic studies with 1H NMR spectroscopy and pyridine additives for mechanistic investigation.

Main Results:

  • Achieved living β-selective cyclopolymerization by imposing steric demands on monomers or catalysts.
  • Demonstrated control over polymer molecular weight and narrow dispersities, tunable by catalyst loading.
  • Successfully synthesized diblock and triblock copolymers across a wide range of monomers.

Conclusions:

  • Steric engineering is crucial for enhancing catalyst stability and controlling initiation/propagation rates in β-selective CP.
  • The developed method provides a robust platform for synthesizing precisely controlled conjugated polymers and block copolymers.
  • This advancement expands the synthetic utility of cyclopolymerization for creating advanced polymer architectures.