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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
2.9K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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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...
5.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.4K
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.
10.4K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.4K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.0K
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?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
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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Two-Step Synthesis, Structure, and Optical Features of a Double Hetero[7]helicene.

Mohamed S H Salem1,2, Ahmed Sabri1, Md Imrul Khalid1

  • 1SANKEN, Osaka University, Ibaraki-shi, Osaka 567-0047, Japan.

Molecules (Basel, Switzerland)
|December 23, 2022
PubMed
Summary

Researchers synthesized a novel double aza-oxa[7]helicene using a two-step process involving acid-mediated annulation and electrochemical reactions. This new molecule

Keywords:
double hetero[7]heliceneelectrochemical cross-couplingnucleus-independent chemical shiftpolycyclic aromatic hydrocarbonshort-step synthesis

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Helicenes are chiral aromatic compounds with unique helical structures.
  • Aza-oxa heterocycles offer tunable electronic and optical properties.
  • Developing novel synthetic routes for complex heterocyclic systems is crucial.

Purpose of the Study:

  • To synthesize a novel double aza-oxa[7]helicene.
  • To investigate the structural and optical characteristics of the synthesized molecule.
  • To understand the photophysical properties through computational analysis.

Main Methods:

  • Two-step synthesis involving acid-mediated annulation.
  • Electrochemical sequential reaction: oxidative coupling and dehydrative cyclization.
  • X-ray crystallographic analysis for structural determination.
  • Density Functional Theory (DFT) calculations for optical property rationalization.

Main Results:

  • Successful synthesis of a novel double aza-oxa[7]helicene.
  • Detailed structural elucidation via X-ray crystallography.
  • Experimental and computational data on absorption and emission behaviors.

Conclusions:

  • The study presents an efficient synthetic strategy for a unique double heterohelicene.
  • The synthesized molecule exhibits interesting structural and photophysical properties.
  • DFT calculations provide insights into the observed optical characteristics.