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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.
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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?
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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 para...

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Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis

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Published on: November 17, 2011

Super-heptazethrene.

Wangdong Zeng¹, Zhe Sun¹, Tun Seng Herng²

¹Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.

Angewandte Chemie (International Ed. in English)

|May 31, 2016

Summary

This summary is machine-generated.

Researchers synthesized super-heptazethrene (SHZ-CF3), a large polycyclic hydrocarbon. This molecule displays a unique diradical character, offering new possibilities for materials science.

Keywords:

polycyclic hydrocarbons quinoids radicals synthetic methods zethrene

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Published on: July 17, 2020

Area of Science:

Organic Chemistry
Materials Science
Polycyclic Aromatic Hydrocarbons

Background:

Heptazethrene derivatives are complex polycyclic aromatic hydrocarbons.
Synthesizing larger, extended versions presents significant challenges.
Understanding their electronic properties, like diradical character, is crucial.

Purpose of the Study:

To report the challenging synthesis of a laterally extended heptazethrene derivative, super-heptazethrene (SHZ-CF3).
To investigate the electronic properties of the synthesized molecule, particularly its diradical character.
To establish a new synthetic route for large-size quinoidal polycyclic hydrocarbons.

Main Methods:

Utilized a synthetic strategy involving multiple selective intramolecular Friedel-Crafts alkylation.
Employed oxidative dehydrogenation as a key step in the synthesis.
Characterized the resulting compounds, including an intermediate dibenzo-terrylene (SHZ-2H).

Main Results:

Successfully synthesized the super-heptazethrene derivative SHZ-CF3.
SHZ-CF3 was found to possess an open-shell singlet diradical ground state.
The diradical character of SHZ-CF3 is significantly larger than that of smaller heptazethrene derivatives.
An intermediate dibenzo-terrylene (SHZ-2H) was also isolated.

Conclusions:

A novel synthetic methodology for accessing large-size quinoidal polycyclic hydrocarbons has been developed.
The synthesized super-heptazethrene exhibits unique electronic properties due to its enhanced diradical character.
This work opens avenues for exploring novel materials with tailored physical properties.