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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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...
3.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
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...
3.2K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

13.2K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
13.2K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.0K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.0K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

6.1K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
6.1K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

11.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
11.0K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Contorted Heteroannulated Tetraareno[a,d,j,m]coronenes.

Xuan Yang1, Frank Rominger1, Michael Mastalerz1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 10, 2021
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Summary

Researchers synthesized novel coronene derivatives with pyridine, anisole, and thiophene rings for organic electronics. This new method allows for greater control over electronic properties by incorporating both electron-donating and -withdrawing groups.

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contorted PAHscoronenecross-couplingphotocyclizationpolycyclic aromatic hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Fused polycyclic aromatic compounds are crucial for organic electronics.
  • Coronenes and heterocoronenes offer tunable photophysical and electrochemical properties.
  • Existing methods limit the variation of fused heteroaromatics on coronene cores, hindering simultaneous electron-donating and -withdrawing group incorporation.

Purpose of the Study:

  • To develop a versatile synthetic route for novel tetraarenocoronene derivatives.
  • To incorporate pyridine, anisole, and thiophene units into the coronene framework.
  • To investigate the structure-property relationships of these new materials.

Main Methods:

  • A facile two-step synthesis involving Suzuki-Miyaura cross-coupling followed by cyclization.
  • Starting materials: three different diarenoperylene dibromides.
  • Characterization: single-crystal X-ray crystallography, UV/Vis spectroscopy, and cyclovoltammetry.

Main Results:

  • Successful synthesis of pyridine, anisole, and thiophene annulated tetraarenocoronenes.
  • Analysis of contorted molecular π-planes using X-ray crystallography.
  • Systematic investigation of photophysical and electrochemical properties.

Conclusions:

  • The developed synthetic route provides access to a wider range of heterocoronene structures.
  • The new materials exhibit tunable electronic properties due to the incorporated heteroaromatic rings.
  • These findings advance the design of advanced materials for organic electronics.