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Related Concept Videos

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

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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A redox-switchable alpha-cyclodextrin-based [2]rotaxane.

Yan-Li Zhao1, William R Dichtel, Ali Trabolsi

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

Journal of the American Chemical Society
|August 6, 2008
PubMed
Summary
This summary is machine-generated.

A novel bistable rotaxane featuring an alpha-cyclodextrin ring and a redox-active tetrathiafulvalene system was synthesized. The alpha-cyclodextrin ring controllably moves between the tetrathiafulvalene and triazole units upon redox stimulation.

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Area of Science:

  • Supramolecular Chemistry
  • Molecular Machines
  • Organic Synthesis

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in nanotechnology.
  • Controlling the movement of molecular components is crucial for developing functional molecular devices.
  • Redox-active units offer a pathway for external control over molecular motion.

Purpose of the Study:

  • To synthesize a bistable [2]rotaxane incorporating a redox-active tetrathiafulvalene (TTF) unit and an alpha-cyclodextrin (alpha-CD) ring.
  • To elucidate the redox-driven movement of the alpha-CD ring between the TTF and triazole moieties.
  • To quantitatively and semiquantitatively establish the preferred binding site of the alpha-CD ring.

Main Methods:

  • Synthesis via Cu(I)-catalyzed azide-alkyne cycloaddition.
  • Microcalorimetric titrations for binding affinity studies.
  • Electrochemical experiments (cyclic voltammetry) for redox-driven switching.
  • Spectroscopic and chiroptical measurements for structural confirmation.

Main Results:

  • Successful synthesis of a bistable [2]rotaxane with alpha-cyclodextrin and a TTF-containing dumbbell.
  • The alpha-cyclodextrin ring preferentially binds to the TTF unit over the triazole unit by an order of magnitude.
  • Redox-induced oxidation of TTF causes the alpha-CD ring to move to the triazole unit.
  • Switching is reversible upon reduction of the oxidized TTF species.

Conclusions:

  • The synthesized bistable [2]rotaxane demonstrates controllable, reversible molecular switching based on redox stimuli.
  • The study provides quantitative evidence for the preferential binding of alpha-cyclodextrin to the TTF unit.
  • This work contributes to the development of redox-addressable molecular machines and switches.