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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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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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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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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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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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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...
3.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Reversible Light-Induced Dimerization of Secondary Face Azobenzene-Functionalized β-Cyclodextrin Derivatives.

Gonzalo Rivero-Barbarroja1, Carlos Fernández-Clavero2, Cristina García-Iriepa2

  • 1Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Sevilla 41012, Spain.

The Journal of Organic Chemistry
|June 21, 2023
PubMed
Summary
This summary is machine-generated.

New beta-cyclodextrin (βCyD) derivatives with azobenzene moieties self-assemble into light-responsive dimers. This controlled self-organization offers potential for advanced supramolecular systems and stimuli-responsive materials.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Aromatic appendage-equipped beta-cyclodextrin (βCyD) derivatives show tunable self-assembly.
  • Aromatic interactions and inclusion phenomena drive supramolecular assembly.
  • Stimuli-responsive, diastereomerically pure systems with low synthetic effort are highly desired.

Purpose of the Study:

  • To synthesize novel βCyD-azobenzene derivatives via click chemistry.
  • To investigate their light-controlled self-organization into dimers.
  • To characterize photoswitching and supramolecular properties for potential applications like gene delivery.

Main Methods:

  • Synthesis of 1,2,3-triazole-linked βCyD-azobenzene derivatives.
  • Characterization using UV-vis absorption, induced circular dichroism, and NMR spectroscopy.
  • Computational modeling and stability studies against guest competitors and varying polarity.

Main Results:

  • Azobenzene moiety successfully clicked to the secondary O-2 position of βCyD.
  • Reversible light-induced self-organization into dimers observed, with monomers facing secondary rims.
  • Dimers stabilized by aromatic-aromatic and partial inclusion interactions; photoswitching to Z-isomer disrupts dimers.

Conclusions:

  • E-configured βCyD-azobenzene derivatives form light-reversible dimers in aqueous solution.
  • Partial reciprocal inclusion and aromatic interactions stabilize the dimeric structure.
  • Spatiotemporal control over supramolecular organization is achievable via photoswitching.