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Related Concept Videos

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
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Radical Chain-Growth Polymerization: Overview01:10

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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Updated: Jun 30, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Molecular Photothermal Conversion Catalyst Promotes Photocontrolled Atom Transfer Radical Polymerization.

Cristina Preston-Herrera1, Sajjad Dadashi-Silab1, Daniel G Oblinsky1

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society
|March 20, 2024
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Summary
This summary is machine-generated.

This study introduces a vitamin B12 derivative as a dual photothermal conversion and catalysis agent for atom transfer radical polymerization (ATRP). This novel catalyst enables rapid, controlled polymerization using visible and near-infrared light.

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Area of Science:

  • Photochemistry
  • Polymer Chemistry
  • Catalysis

Background:

  • Photothermal conversion efficiently converts light to heat, but its integration with catalysis is limited.
  • Porphyrinic compounds naturally utilize nonradiative relaxation for light-to-heat conversion.
  • Developing dual photothermal conversion and catalysis systems is crucial for advancing light-driven transformations.

Purpose of the Study:

  • To explore the photothermal conversion catalytic activity of a vitamin B12 derivative for polymerization.
  • To achieve controlled atom transfer radical polymerization (ATRP) under light irradiation.
  • To demonstrate temporal control in photocontrolled thermal polymerization.

Main Methods:

  • Utilized heptamethyl ester cobyrinate (HME-Cob), a vitamin B12 derivative, as a photothermal catalyst.
  • Employed atom transfer radical polymerization (ATRP) under visible and near-infrared light irradiation.
  • Incorporated a photoinitiator for light-induced catalyst regeneration and temporal control.

Main Results:

  • HME-Cob demonstrated effective photothermal conversion and catalytic activity for ATRP.
  • Rapid polymerization was achieved with good control under photothermal activation.
  • Exquisite temporal control was observed in photocontrolled thermal polymerization across a broad wavelength range.
  • The catalyst showed efficacy with near-infrared light, expanding application possibilities.

Conclusions:

  • Vitamin B12 derivatives can function as effective photothermal conversion catalysts for polymerization.
  • This approach offers precise temporal control over light-induced polymerization.
  • The findings highlight the potential for developing novel photothermal catalysts for various applications.