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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Radical Formation: Addition00:47

Radical Formation: Addition

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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.8K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

3.8K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
3.8K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K

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Updated: Jul 2, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Modulating β-Keto-enamine-Based Covalent Organic Frameworks for Photocatalytic Atom-Transfer Radical Addition

Yuting Zhao1, Lei Li1, Jiyuan Zang1

  • 1College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 25, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces novel covalent organic frameworks (COFs) as efficient photocatalysts for atom-transfer radical addition (ATRA) reactions. A chlorine-functionalized COF demonstrated high activity and recyclability under visible light.

Keywords:
alkeneatom-transfer radical additionbifunctionalizationcovalent organic frameworkspolyhalogenated hydrocarbons

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photocatalysis

Background:

  • Atom-transfer radical addition (ATRA) reactions form C-C and C-halogen bonds.
  • Conventional photosensitizers like metal complexes and organic dyes pose toxicity and recyclability challenges.
  • Development of sustainable and efficient photocatalysts is crucial for green chemistry.

Purpose of the Study:

  • To synthesize and evaluate novel β-ketoenamine-linked covalent organic frameworks (COFs) as heterogeneous photocatalysts.
  • To investigate the photocatalytic activity of COFs in the ATRA reaction under visible light.
  • To assess the recyclability and functional group tolerance of the developed COF photocatalysts.

Main Methods:

  • Synthesis of three β-ketoenamine-linked COFs using 1,3,5-triformylphloroglucinol and 1,4-phenylenediamines.
  • Characterization of COFs' transient photocurrent and photocatalytic properties.
  • Evaluation of COF photocatalytic performance in the ATRA reaction of polyhalogenated alkanes to halogenated olefins.

Main Results:

  • The synthesized COFs exhibited variable photocatalytic activities.
  • A COF functionalized with electron-deficient chlorine atoms showed superior performance in the ATRA reaction.
  • The chlorine-containing COF facilitated the formation of halogenated olefins under visible light at room temperature.
  • This heterogeneous photocatalyst demonstrated good functional group tolerance and recyclability.

Conclusions:

  • Novel β-ketoenamine-linked COFs can serve as effective and recyclable heterogeneous photocatalysts.
  • Chlorine-functionalized COFs show enhanced activity for ATRA reactions.
  • These COFs offer a sustainable alternative to traditional photosensitizers for organic synthesis.