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Related Concept Videos

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...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
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...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Molecular Shape and Polarity03:37

Molecular Shape and Polarity

Dipole Moment of a Molecule
Newman Projections02:06

Newman Projections

Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Mesomorphic [2]rotaxanes: sheltering ionic cores with interlocking components.

Natalie D Suhan1, Stephen J Loeb, S Holger Eichhorn

  • 1Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, N9B 3P4, Canada.

Journal of the American Chemical Society
|December 11, 2012
PubMed
Summary
This summary is machine-generated.

Researchers developed liquid crystalline [2]rotaxanes with tunable properties. Sheltering ionic cores with macrocycles enhanced thermal stability and fluidity, with linear side chains promoting smectic phases and branched chains inducing soft crystal phases.

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Liquid Crystals

Background:

  • Liquid crystalline [2]rotaxanes are advanced materials with potential applications.
  • Tetracatenar motifs form the basis for these rotaxane structures.
  • Ionic cores significantly influence molecular properties.

Purpose of the Study:

  • To synthesize and characterize dicationic and tetracationic liquid crystalline [2]rotaxanes.
  • To investigate the effect of macrocycle-sheltering on mesomorphism and thermal stability.
  • To explore the impact of side chain architecture (linear vs. branched) and charge density on material behavior.

Main Methods:

  • Synthesis of tetracationic and dicationic [2]rotaxanes with ester and pyridinium stoppers.
  • Comparative analysis with dumbbell-shaped analogs.
  • Varying side chain length and branching (aliphatic vs. siloxane).
  • Thermal analysis (DSC, TGA) to determine mesophase behavior and stability.

Main Results:

  • [2]Rotaxanes with linear side chains and specific chain-to-core volume ratios exhibited smectic liquid crystal phases.
  • Increasing side chain ratios broadened the smectic A phase range but exceeded decomposition temperatures.
  • Transition from tetracationic to dicationic rotaxanes improved fluidity, thermal, and chemical stability.
  • Branched side chains induced soft crystal phases, while non-rotaxane analogs showed only soft crystals.

Conclusions:

  • Macrocycle-induced ion-core sheltering significantly impacts mesomorphism and stability in liquid crystalline [2]rotaxanes.
  • Side chain structure and charge density are critical for controlling liquid crystalline phase behavior.
  • The design of [2]rotaxanes offers a route to tune material properties for specific applications.