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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
2.8K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.2K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.8K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

2.6K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies.

Soh Ishikawa1, Kazuhisa Yamasumi1, Shinya Sugiura1

  • 1Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University Kusatsu 525-8577 Japan maedahir@ph.ritsumei.ac.jp.

Chemical Science
|May 24, 2024
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Summary

Novel norcorrole derivatives self-assemble into triple-decker structures, forming liquid crystals with high electrical conductivity. These findings advance materials science for electronic applications.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Norcorrole derivatives are macrocyclic compounds with potential applications in materials science.
  • Controlling molecular assembly is key to developing materials with specific electronic properties.

Purpose of the Study:

  • To synthesize norcorrole derivatives with trialkoxyphenyl groups.
  • To investigate the self-assembly behavior of these derivatives in single crystals and liquid crystals.
  • To explore the relationship between molecular structure, assembly, and electrical conductivity.

Main Methods:

  • Synthesis of norcorrole derivatives with varying aliphatic chain lengths.
  • Crystallography to determine single-crystal structures.
  • Polarized optical microscopy and differential scanning calorimetry for liquid crystal characterization.
  • Molecular dynamics simulations to support experimental findings.

Main Results:

  • Norcorrole derivatives formed various stacking assemblies based on aliphatic chain length.
  • Triple-decker stacking structures were observed in both single-crystal and liquid crystal states.
  • The liquid crystalline state exhibited discotic columnar structures composed of triple deckers.
  • High electrical conductivity was observed in the liquid crystalline state.

Conclusions:

  • The length of aliphatic chains on trialkoxyphenyl moieties influences the self-assembly of norcorrole derivatives.
  • Triple-decker assemblies are achievable in both solid and liquid crystalline states.
  • Discotic columnar liquid crystals formed by these norcorrole derivatives show promise for high electrical conductivity applications.