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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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...
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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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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.
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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,...
4.4K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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A Negatively Curved Pyrene-Fused Azaacene.

Marco Carini1, Miguel Martín-Arroyo1, Manuel Melle-Franco2

  • 1POLYMAT, Department of Applied Chemistry, University of the Basque Country (EHU), Donostia-San Sebastián, Spain.

Angewandte Chemie (International Ed. in English)
|April 30, 2026
PubMed
Summary
This summary is machine-generated.

Researchers created a bent, saddle-shaped molecule from aromatic hydrocarbons using steric overcrowding. This novel structure exhibits unique optoelectronic properties due to its non-planar, negatively curved π-framework.

Keywords:
curved aromaticsovercrowdingpolycyclic aromatic hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Non-planar aromatic hydrocarbons possess unique optoelectronic properties due to distorted π-frameworks.
  • Steric overcrowding typically induces twisting (helical or alternate) in aromatic hydrocarbons.
  • Bent, non-planar structures are rare in this class of compounds.

Purpose of the Study:

  • To synthesize and characterize a novel pyrene-fused azaacene derivative.
  • To investigate the generation of bent, non-planar aromatic structures via steric overcrowding.
  • To explore the resulting optoelectronic properties of such negatively curved molecules.

Main Methods:

  • Synthesis of a pyrene-fused azaacene derivative with eight phenyl substituents.
  • Single-crystal X-ray diffraction analysis to determine molecular structure.
  • Computational modeling to understand π-framework distortion and stabilization.

Main Results:

  • A novel, negatively curved, saddle-shaped molecular structure was successfully synthesized.
  • Eight phenyl substituents enforced bending of the aromatic core, achieving bend angles of 41° and 34°.
  • Intramolecular π-π stacking between phenyl rings stabilized the non-planar conformation.

Conclusions:

  • Steric overcrowding can be utilized to create bent, saddle-shaped aromatic architectures, complementing existing twisting strategies.
  • The synthesized molecule exhibits significant deviation from planarity, leading to unique structural and electronic characteristics.
  • This work expands the scope of non-planar aromatic hydrocarbons for potential applications in optoelectronics.