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Related Concept Videos

Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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.
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...

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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
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Published on: December 23, 2016

Switchable V-type [2]pseudorotaxanes.

Hongyuan Zhang1, Qiaochun Wang, Minhua Liu

  • 1Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, PR China.

Organic Letters
|July 4, 2009
PubMed
Summary
This summary is machine-generated.

A novel V-type molecule forms distinct pseudorotaxanes with cucurbit[7]uril. Protonation reversibly switches the cucurbit[7]uril position, changing the solution color.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Supramolecular chemistry explores host-guest interactions.
  • Cucurbit[7]uril (CB[7]) is a macrocyclic host with unique binding properties.
  • Controlling host-guest complexation is key for developing responsive materials.

Purpose of the Study:

  • To synthesize a V-type molecule with distinct binding sites.
  • To investigate the formation of pseudorotaxanes with cucurbit[7]uril.
  • To explore the stimuli-responsive behavior of these supramolecular assemblies.

Main Methods:

  • Synthesis of a V-type molecule containing a cyanine branch and an aminophenoxy ethyl arm.
  • Formation of [2]pseudorotaxanes using cucurbit[7]uril as the host in aqueous solution.
  • Protonation of the aniline group to induce host displacement and observe color changes.

Main Results:

  • Successful synthesis of the V-type molecule.
  • Formation of distinct [2]pseudorotaxanes with cucurbit[7]uril, with the host binding to either the cyanine or aminophenoxy ethyl moiety.
  • Reversible switching of cucurbit[7]uril between the two branches upon protonation/deprotonation.
  • Visible color change of the solution from orange-red to yellow, indicating a change in the electronic structure.

Conclusions:

  • The synthesized V-type molecule acts as a tunable platform for forming switchable pseudorotaxanes.
  • Proton-responsive host displacement within the pseudorotaxane structure is demonstrated.
  • The observed color change highlights the potential for developing visual sensors or responsive dyes.