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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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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
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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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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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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Related Experiment Video

Updated: May 16, 2025

Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch
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Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch

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Computational Rational Design of Bridgehead Nitrogen Heterocyclic Azobenzene Photoswitches.

Dunja Pupavac1, Andrea M Nikolić2, John-Paul Webster3

  • 1Innovative Centre, Faculty of Chemistry, Ltd., Studentski Trg 12-16, 11158 Belgrade, Serbia.

The Journal of Organic Chemistry
|May 15, 2025
PubMed
Summary

Researchers developed a computational method to design novel heteroaryl azobenzene photoswitches. This approach accelerates the discovery of molecules with improved spectral properties, like red-shifted absorption maxima.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Azobenzenes are versatile molecular photoswitches used in various fields.
  • Their photochromic properties depend on structure and substitution.
  • Designing new azobenzenes often requires synthesizing large compound libraries.

Purpose of the Study:

  • To develop a computational workflow for designing novel heteroaryl azobenzene photoswitches.
  • To synthesize and evaluate photoswitching properties of new compounds.
  • To create azobenzene derivatives with improved spectral characteristics.

Main Methods:

  • Computational design and in silico evaluation of photoswitch candidates.
  • Synthesis of a small library of heteroaryl azobenzenes, including pyrazolo[1,5-a]pyrimidine and 1,2,4-triazolo[1,5-a]pyrimidine derivatives.
  • Photochemical property evaluation and validation of computational models.

Main Results:

  • A novel class of heteroaryl azobenzene photoswitches was designed and synthesized.
  • The computational approach was validated using experimental photochemical data.
  • A new photoswitch with red-shifted absorption maxima (λmax) was successfully synthesized.

Conclusions:

  • A computationally driven workflow enables efficient design of azobenzene photoswitches.
  • Incorporating N-bridgehead heterocycles offers a strategy for improved photoswitching properties.
  • This method accelerates the discovery of advanced molecular photoswitches.