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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
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

3.0K
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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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.5K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.2K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
4.2K
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10.3K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.3K

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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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Hetero-Hydrazone Photoswitches.

Daniil Sosnin1, Syed Ali Abbas Abedi2, Mohammad Izadyar2

  • 1Department of Chemistry, Dartmouth College, Hanover, NH, 03755, USA.

Angewandte Chemie (International Ed. in English)
|September 10, 2025
PubMed
Summary
This summary is machine-generated.

Incorporating specific heterocycles into molecular photoswitches significantly impacts their switching efficiency and stability. Understanding heterocycle basicity and hydrogen-bonding is key to designing advanced photoswitch systems.

Keywords:
BasicityHeterocycleHydrazonePhotoswitchSecondary H‐bonding

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Area of Science:

  • Molecular switches
  • Organic chemistry
  • Photophysics

Background:

  • Molecular photoswitches are crucial for advanced applications.
  • Incorporating heterocycles into photoswitch scaffolds is a recent strategy.
  • Hydrazone-based photoswitches are under investigation for property tuning.

Purpose of the Study:

  • To assess the influence of heterocyclic rings on hydrazone-based photoswitch systems.
  • To examine how heterocycles impact photoswitching efficiency and bistability.
  • To establish design principles for tuning photoswitch performance.

Main Methods:

  • Synthesis of novel photoswitch compounds.
  • Evaluation of photoswitching efficiency and properties.
  • Theoretical calculations using time-dependent density-functional theory (TD-DFT).
  • Structure-property relationship analysis.

Main Results:

  • Heterocycles with basic nitrogen and hydrogen-bonding sites (e.g., imidazole) exhibit poor switching efficiency and rapid thermal back-isomerization.
  • Less basic heterocycles (e.g., benzoxazole, benzothiazole) promote inversion pathways, enhancing bistability.
  • Hydrazones without secondary hydrogen-bonding sites show improved photostationary states, quantum yields, and red-shifted activation wavelengths.
  • Heterocycle basicity, electron-donating ability, and hydrogen-bonding sites critically influence photoswitching efficiency.

Conclusions:

  • Heterocycle selection is vital for optimizing molecular photoswitch performance.
  • Design principles for enhanced bistability and efficiency in hydrazone photoswitches are identified.
  • This study provides insights into tuning photoswitch properties through rational heterocycle incorporation.