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Related Concept Videos

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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

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

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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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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Related Experiment Video

Updated: Jun 13, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Post-Synthetic Modification of the C═C Linkage in a Vinylene-Linked COF for ROS-Mediated Enamine Dimerization.

Hongryeol Yun1, Eunji Kim1, Ha Yeon Kim1

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

Small (Weinheim an Der Bergstrasse, Germany)
|June 12, 2026
PubMed
Summary

This study demonstrates a new method for modifying vinylene-linked covalent organic frameworks (COFs) via ruthenium-catalyzed arylation. This functionalization enhances their photocatalytic efficiency for ROS-driven reactions.

Keywords:
covalent organic frameworksphotocatalysispost‐synthetic modification (PSM)reactive oxygen species (ROS)

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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

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Last Updated: Jun 13, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
11:09

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Area of Science:

  • Materials Science
  • Catalysis
  • Organic Chemistry

Background:

  • Vinylene-linked covalent organic frameworks (COFs) are promising photocatalysts due to their stability and π-conjugation.
  • Post-synthetic modification (PSM) of the vinylene linkage in COFs is difficult.
  • Developing new methods for COF functionalization is crucial for advancing their applications.

Purpose of the Study:

  • To develop a method for direct C═C linkage modification in vinylene-linked COFs.
  • To investigate the impact of this modification on photocatalytic activity.
  • To explore the mechanism of enhanced photocatalysis.

Main Methods:

  • Ruthenium-catalyzed arylation of a vinylene-linked COF using 4-bromobenzonitrile.
  • Characterization of the modified COF (COF-PhCN) and pristine COF (COF-H).
  • Photocatalytic experiments monitoring reactive oxygen species (ROS) generation and enamine dimerization.

Main Results:

  • Successful arylation at the C═C linkage, yielding COF-PhCN.
  • COF-PhCN exhibited enhanced generation of singlet oxygen (1O2) and superoxide radicals (O2·-).
  • COF-PhCN achieved significantly faster enamine dimerization conversion (3 h vs. 12 h) and demonstrated recyclability over five cycles.

Conclusions:

  • The arylation strategy effectively functionalizes vinylene-linked COFs at the C═C linkage.
  • Enhanced photocatalytic activity is attributed to restricted rotation and promoted intersystem crossing.
  • This work presents the first COF-catalyzed enamine dimerization and a novel route for ROS-driven photocatalysis.