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Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

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...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

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...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

Aromatic Compounds: Overview

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...

Basicity of Aromatic Amines

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

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Updated: Feb 3, 2026

A Modified QuEChERS-HPLC Method for Detection of Polycyclic Aromatic Hydrocarbons in Zebrafish Embryos Exposed to Fine Particulate Matter

A Modified QuEChERS-HPLC Method for Detection of Polycyclic Aromatic Hydrocarbons in Zebrafish Embryos Exposed to Fine Particulate Matter

Published on: June 13, 2025

Helical Ullazine-Quinoxaline-Based Polycyclic Aromatic Hydrocarbons.

Marcus Richter¹, Sebastian Hahn², Evgenia Dmitrieva³

¹Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Dresden University of Technology, Institute for Molecular Functional Materials, Mommsenstrasse 4, 01069, Dresden, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|November 7, 2018

Summary

This study introduces a new method for synthesizing helical nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs) using polycyclic aromatic azomethine ylides (PAMYs). These novel compounds exhibit excellent optical and redox properties, suggesting potential applications in organic electronics.

Keywords:

azaacene cycloaddition helical structures heterocycles polycyclic aromatic hydrocarbons

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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

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A Modified QuEChERS-HPLC Method for Detection of Polycyclic Aromatic Hydrocarbons in Zebrafish Embryos Exposed to Fine Particulate Matter

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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Polycyclic aromatic azomethine ylides (PAMYs) are key precursors for synthesizing nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs).
Previous syntheses often involved symmetric quinones, limiting structural diversity.

Purpose of the Study:

To develop a novel synthetic route to helical N-PAHs using asymmetric ortho-quinones and PAMYs.
To investigate the structural, optical, and redox properties of the synthesized compounds.

Main Methods:

1,3-cycloaddition reactions of PAMYs with asymmetric ortho-quinones.
Single-crystal X-ray analysis and computational modeling for structural elucidation.
In situ EPR/UV/Vis-NIR spectroelectrochemistry for property investigation.

Main Results:

Successful synthesis of three helical N-PAHs with ullazine-quinoxaline (UQ-1-3) backbones.
UQ-3 demonstrated a stable geometry with four helical centers in a (P,P,M,M) configuration.
Redox properties correlated with the number of ullazine/quinoxaline units; excellent optical and redox characteristics observed.

Conclusions:

The study presents a versatile method for creating complex helical N-PAHs.
The synthesized UQ compounds show promise for applications as chiral emitters or ambipolar charge transport materials in organic electronics due to their unique optical and redox properties.