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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

2.6K
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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Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

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Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
8.5K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.2K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Cooperative Allosteric Transitions01:58

Cooperative Allosteric Transitions

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Updated: Nov 2, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Singlet oxygen stimulus for switchable functional organic cages.

Cédric Mongin1, Alejandro Mendez Ardoy1, Raphaël Méreau1

  • 1Université de Bordeaux, CNRS, Bordeaux INP, ISM UMR 5255 351 cours de la Libération 33400 Talence France dario.bassani@u-bordeaux.fr brigitte.bibal@u-bordeaux.fr.

Chemical Science
|June 7, 2021
PubMed
Summary
This summary is machine-generated.

New molecular cages with a 9,10-diphenylanthracene (DPA) chromophore show reversible endoperoxide formation. This transformation significantly alters metal ion binding, enhancing selectivity for sodium (Na+) and cesium (Cs+) ions.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Molecular cages are crucial for host-guest chemistry and molecular recognition.
  • The 9,10-diphenylanthracene (DPA) moiety is a known photosensitizer and reactive group.
  • Controlling cavity size and guest binding in molecular cages remains a significant challenge.

Purpose of the Study:

  • To synthesize novel molecular cages incorporating a DPA chromophore.
  • To investigate the reversible endoperoxide formation and its impact on cage structure.
  • To evaluate the modulation of metal ion binding properties upon endoperoxide formation.

Main Methods:

  • Templated ring-closure metathesis for cage synthesis.
  • Photogeneration of singlet oxygen for reversible Diels-Alder reaction.
  • Spectroscopic and binding studies to characterize cage properties.
  • Density Functional Theory (DFT) calculations for structural analysis.

Main Results:

  • Successful synthesis of molecular cages 1a and 2a with tunable cavity sizes.
  • Reversible conversion between DPA cages (1a, 2a) and endoperoxide cages (1b, 2b) via singlet oxygen.
  • Endoperoxide formation introduces new coordination sites and alters internal cage geometry.
  • Significant modulation of Na+ and Cs+ binding constants (4-450 fold) upon endoperoxide formation.

Conclusions:

  • Reversible covalent modification of molecular cages can precisely tune metal ion binding.
  • The endoperoxide cages exhibit enhanced affinity and altered coordination preferences for alkali metal cations.
  • This work presents a novel strategy for designing responsive molecular receptors.