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Related Concept Videos

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...
3.6K
Ion Exchange01:17

Ion Exchange

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Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
1.1K
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 para...
3.6K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
3.5K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

13.5K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
13.5K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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An In Vitro Enzymatic Assay to Measure Transcription Inhibition by GalliumIII and H3 5,10,15-trispentafluorophenylcorroles
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Two Cationic Antiaromatic Free-Base Corroles.

Pengfei Li1, Fan Wu2, Chulin Qu1

  • 1State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.

Organic Letters
|September 19, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel cationic free-base antiaromatic corroles, BC(H2)+ and BC(H4)3+, using a unique annulation strategy. This breakthrough overcomes challenges in creating these unusual, non-planar aromatic compounds.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Porphyrinoids are vital macrocyclic compounds with diverse applications.
  • Synthesizing antiaromatic porphyrinoids, especially free-base variants, presents significant synthetic hurdles.
  • Controlling the geometry and electronic properties of these systems is crucial for their function.

Purpose of the Study:

  • To report the first successful synthesis of cationic free-base antiaromatic corroles.
  • To introduce a novel synthetic strategy employing beta-annulated benzene rings to stabilize these reactive species.
  • To characterize the structural and electronic properties of the synthesized compounds.

Main Methods:

  • A strategy involving beta-annulated benzene rings was employed to direct the synthesis.
  • Crystallographic analysis was used to determine the solid-state structures.
  • Spectroscopic techniques (e.g., NMR, UV-Vis) were utilized for characterization.
  • Theoretical calculations were performed to understand electronic properties and confirm antiaromaticity.

Main Results:

  • Two novel cationic free-base antiaromatic corroles, BC(H2)+ and BC(H4)3+, were successfully synthesized.
  • BC(H2)+ exhibits a slightly saddle-shaped geometry, while BC(H4)3+ shows a severely distorted saddle shape.
  • Crystallographic, spectroscopic, and computational data robustly confirmed the antiaromatic nature of both compounds.
  • The beta-annulation strategy effectively suppressed unwanted side reactions during synthesis.

Conclusions:

  • The study presents the first examples of cationic free-base antiaromatic corroles.
  • The developed synthetic approach provides a viable route to access challenging antiaromatic porphyrinoid systems.
  • These findings expand the scope of known porphyrinoid structures and offer new platforms for exploring antiaromaticity in macrocyclic chemistry.