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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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...
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Dipole Moment of a Molecule
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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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Stability of Substituted Cyclohexanes02:30

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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...
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Stereoisomerism of Cyclic Compounds02:33

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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,...
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Conformations of Butane02:20

Conformations of Butane

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Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Shape-Persistent, Sterically Crowded Star Mesogens: From Exceptional Columnar Dimer Stacks to Supermesogens.

Matthias Lehmann1, Philipp Maier2

  • 1Institut of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg (Germany). Matthias.Lehmann@uni-wuerzburg.de.

Angewandte Chemie (International Ed. in English)
|June 24, 2015
PubMed
Summary

Shape-persistent star mesogens with pyridyl groups form unique dimers and helical packing in columnar liquid crystal phases. This host material can encapsulate guest molecules, acting as an endoreceptor for functional columnar structures.

Keywords:
columnar phasesendoreceptorshexasubstituted benzenesliquid crystalsstar mesogens

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Liquid Crystals

Background:

  • Hexasubstituted C3-symmetric benzenes with oligophenylenevinylene (OPV) arms and pyridyl/phenyl substituents exhibit shape persistence.
  • These star mesogens are sterically crowded at the core, leading to significant void spaces between arms in condensed phases.

Purpose of the Study:

  • To investigate the self-assembly behavior of these star mesogens in neat form and in the presence of carboxylic acids.
  • To explore the potential of these mesogens as host materials for guest molecules within liquid crystal phases.

Main Methods:

  • Synthesis of hexasubstituted C3-symmetric benzene derivatives with OPV arms and pyridyl/phenyl groups.
  • Characterization of mesophase behavior using techniques such as polarized optical microscopy and differential scanning calorimetry.
  • Structural analysis of neat and guest-host systems to understand molecular packing and interactions.

Main Results:

  • Neat star mesogens form dimers and exhibit short-range helical packing in columnar mesophases.
  • The pyridyl derivative forms a thermodynamically stable mesophase.
  • This pyridyl compound acts as a host, forming star-shaped supermesogens that encapsulate carboxylic acids as monomers within columnar stacks.

Conclusions:

  • The star mesogens, particularly the pyridyl derivative, demonstrate unique self-assembly into columnar structures.
  • The pyridyl-based host material functions as an effective liquid crystal endoreceptor, fully enclosing guest molecules.
  • This discovery opens avenues for designing novel columnar functional materials with encapsulated guests.