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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

17.5K
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...
17.5K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.5K
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...
4.5K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

22.0K
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...
22.0K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

16.9K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
16.9K
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

24.1K
Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...
24.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.5K
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...
4.5K

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Updated: Apr 20, 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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Shape-persistent arylene ethynylene organic hosts for fullerenes.

Chao Yu1, Yinghua Jin, Wei Zhang

  • 1Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO, 80309, USA.

Chemical Record (New York, N.Y.)
|December 3, 2014
PubMed
Summary
This summary is machine-generated.

Researchers developed shape-persistent organic cages using alkyne metathesis. These covalent molecules offer controlled guest binding and show potential for fullerene purification applications.

Keywords:
cage compoundsdynamic covalent chemistryfullerenesmetathesisreceptors

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Shape-persistent host molecules are explored as alternatives to supramolecular architectures.
  • Dynamic covalent chemistry enables the assembly of complex organic molecules with defined cavities.
  • Alkyne metathesis is an emerging dynamic covalent reaction forming rigid, linear acetylene linkages.

Purpose of the Study:

  • To describe the dynamic assembly of shape-persistent arylene ethynylene cages.
  • To investigate cages with various shapes and sizes.
  • To explore cage-fullerene binding and purification applications.

Main Methods:

  • One-step alkyne metathesis for cage assembly.
  • Synthesis of shape-persistent arylene ethynylene cages.
  • Investigation of cage-fullerene interactions.

Main Results:

  • Successfully assembled shape-persistent arylene ethynylene cages of diverse shapes and sizes.
  • Demonstrated controlled binding between cages and fullerenes.
  • Identified potential for fullerene purification using these covalent cages.

Conclusions:

  • Alkyne metathesis is effective for constructing complex, shape-persistent covalent cages.
  • These cages exhibit tunable properties for specific guest binding.
  • The developed cages show promise for advanced separation technologies like fullerene purification.