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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

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 with both...
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UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...
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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 overlap of p...
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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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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, respectively.
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When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...

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Updated: May 18, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Undecaphenylcorroles.

Steffen Berg1, Kolle E Thomas, Christine M Beavers

  • 1Department of Chemistry and Center for Theoretical and Computational Chemistry, University of Tromsø, 9037 Tromsø, Norway.

Inorganic Chemistry
|September 8, 2012
PubMed
Summary
This summary is machine-generated.

This study introduces undecaphenylcorrole (UPC) derivatives, revealing that β-aryl substituents significantly influence copper corrole structure and redox potentials. These findings offer new insights into tuning corrole properties for potential applications.

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Area of Science:

  • Supramolecular Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Corrole complexes are vital in catalysis and medicine.
  • Understanding substituent effects is key to designing functional corroles.
  • Undecaphenylcorrole (UPC) derivatives offer a unique structural platform.

Purpose of the Study:

  • To synthesize and characterize novel undecaphenylcorrole (UPC) derivatives.
  • To investigate the impact of β-aryl substituents on copper corrole structure and electronic properties.
  • To compare the effects of β- versus meso-substituents on redox potentials.

Main Methods:

  • Suzuki-Miyaura coupling for synthesis of Cu-UPC derivatives.
  • Single-crystal X-ray diffraction for structural analysis.
  • Electrochemical and UV-Vis absorption spectroscopy for electronic property evaluation.

Main Results:

  • Successfully synthesized three Cu-UPC derivatives with varying para substituents (CF(3), H, CH(3)).
  • X-ray structure revealed a saddled macrocycle conformation in a Cu-UPC complex.
  • Electrochemical studies showed β-phenyl substituents tune redox potentials more effectively than meso-substituents.

Conclusions:

  • β-Aryl substituents significantly impact the macrocycle conformation and electronic properties of copper corroles.
  • The study provides crucial comparative data on substituent effects in corrole chemistry.
  • Findings advance the rational design of tailored copper corrole complexes.