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Related Concept Videos

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
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

20.7K
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...
20.7K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.9K
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...
16.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.2K
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...
4.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

13.6K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
13.6K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.2K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.2K

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Updated: Mar 19, 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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Cylindrical Cycloparaphenylene Triple-Decker.

Zhuofan Xu1, Xingchi Liu1, Xiaonan Ma1

  • 1Department of Chemistry, Institute of Molecular Plus, Tianjin University, Tianjin, P. R. China.

Angewandte Chemie (International Ed. in English)
|March 18, 2026
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel cycloparaphenylene triple-decker molecule (CPP-TD), achieving the first persistent molecular cylinder. This breakthrough enables new host-guest complex formation and optical applications.

Keywords:
cyclocondensationcycloparaphenylenefluorescencenanocarbonsupramolecular chemistry

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • The synthesis of discrete molecular cylinders, specifically those composed of axially aligned cycloparaphenylene (CPP) units, has been a significant challenge in chemical research.
  • Achieving persistent cylindrical geometries in discrete molecular structures is crucial for developing advanced functional materials.

Purpose of the Study:

  • To report the first successful synthesis and characterization of a well-defined cycloparaphenylene triple-decker molecule (CPP-TD).
  • To investigate the structural stability, conformational persistence, and host-guest properties of the synthesized CPP-TD molecule.

Main Methods:

  • Stereoselective cyclocondensation reaction for efficient synthesis of the CPP-TD molecule.
  • X-ray crystallographic analysis to determine solid-state structure and conformation.
  • Spectroscopic studies (e.g., NMR, UV-Vis) to confirm structural integrity and properties in solution.

Main Results:

  • Successful bottom-up synthesis of a discrete CPP triple-decker molecule (CPP-TD) with a persistent cylindrical geometry.
  • X-ray crystallography confirmed a rigid cis-cis cylindrical conformation, maintained in solution.
  • The molecule exhibits attractive van der Waals (vdW) interactions between CPP layers, ensuring shape persistency.
  • CPP-TD displayed unique optical properties and strong binding affinity for fullerene C70, forming a 1:2 host-guest complex.

Conclusions:

  • The development of CPP-TD represents a significant advancement in the synthesis of complex molecular architectures.
  • The persistent cylindrical shape and tunable electronic properties of CPP-TD open avenues for applications in molecular recognition and optical devices.
  • The strong host-guest complexation with C70 highlights the potential of CPP-TD in supramolecular chemistry and materials science.