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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

20.5K
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...
20.5K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.8K
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...
16.8K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.2K
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...
4.2K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

8.1K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
8.1K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

4.7K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.7K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
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...
4.1K

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Related Experiment Video

Updated: Mar 14, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Pentaindenocorannulene: Properties, Assemblies, and C60 Complex.

Samuel Lampart1, Loïc M Roch1, Amit K Dutta1,2

  • 1Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland.

Angewandte Chemie (International Ed. in English)
|October 7, 2016
PubMed
Summary
This summary is machine-generated.

Pentaindenocorannulene, a deep bowl hydrocarbon, accepts four electrons and forms unique nested complexes. This study details its structure, electronic properties, and assembly behavior.

Keywords:
C60corannulenescyclic voltammetrydynamic NMR spectroscopypolycyclic aromatic hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Polynuclear aromatic hydrocarbons (PAHs) are crucial in materials science.
  • Bowl-shaped PAHs offer unique electronic and structural properties.
  • Understanding self-assembly is key for designing advanced materials.

Purpose of the Study:

  • To synthesize and characterize pentaindenocorannulene (1).
  • To investigate the electron accepting capabilities of pentaindenocorannulene.
  • To explore the self-assembly and complex formation of pentaindenocorannulene.

Main Methods:

  • Single-crystal X-ray diffraction for structural analysis.
  • Spectroscopic techniques (UV-Vis, NMR) for electronic characterization.
  • Computational modeling to understand electronic structure and interactions.

Main Results:

  • Pentaindenocorannulene (C50H20) was synthesized and structurally characterized.
  • The molecule exhibits a deep bowl conformation and accepts up to 4 electrons.
  • Columnar bowl-in-bowl assemblies were observed, leading to a nested C60@12 complex.

Conclusions:

  • Pentaindenocorannulene demonstrates significant electron accepting ability.
  • Its unique bowl shape facilitates self-assembly into ordered columnar structures.
  • The formation of nested C60@12 complexes highlights potential applications in molecular encapsulation.