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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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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...
3.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.1K
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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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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...
3.1K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.7K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.7K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

10.4K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
10.4K

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Updated: Oct 14, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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An Expanded 2D Fused Aromatic Network with 90-Ring Hexagons.

Alberto Riaño1, Karol Strutyński2, Meng Liu3

  • 1POLYMAT, University of the Basque Country UPV/EHU, Avenida de Tolosa 72, 20018, Donostia-San Sebastián, Spain.

Angewandte Chemie (International Ed. in English)
|November 8, 2021
PubMed
Summary

Researchers synthesized a novel, expanded two-dimensional fused aromatic network (2D FAN) with 90-ring hexagons. This breakthrough overcomes limitations in creating larger 2D FANs, paving the way for new applications.

Keywords:
2D polymersconjugated 2D polymersconjugated microporous polymersfused aromatic networkspolycyclic aromatic hydrocarbons

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Two-dimensional fused aromatic networks (2D FANs) are advanced materials offering an alternative to graphene.
  • The development of larger lattice dimensions in 2D FANs is crucial for unlocking novel applications.
  • Current synthesis methods and monomer availability limit the creation of larger 2D FAN analogues.

Purpose of the Study:

  • To report the synthesis and characterization of an expanded 2D FAN with unprecedented lattice dimensions.
  • To address the limitations in producing larger 2D FAN structures.
  • To investigate the properties of these novel, large-scale 2D FANs.

Main Methods:

  • Development of novel synthetic strategies to overcome limitations in monomer design and reaction pathways.
  • Characterization of the synthesized material using advanced spectroscopic and microscopic techniques.
  • Exploration of the structural and electronic properties of the expanded 2D FAN.

Main Results:

  • Successful synthesis of a 2D FAN featuring 90-ring hexagons, significantly larger than previously reported structures.
  • Demonstration of a viable method for creating larger-scale 2D FANs.
  • Initial characterization revealing unique structural and electronic properties.

Conclusions:

  • The study presents a significant advancement in the synthesis of large-scale 2D FANs.
  • The developed methodology enables the creation of 2D FANs with larger lattice dimensions.
  • This work opens new avenues for the application of 2D FANs in various fields.