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Related Concept Videos

Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends on...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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A Simple and Scalable Fabrication Method for Organic Electronic Devices on Textiles
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A Simple and Scalable Fabrication Method for Organic Electronic Devices on Textiles

Published on: March 13, 2017

Rylene and related diimides for organic electronics.

Xiaowei Zhan1, Antonio Facchetti, Stephen Barlow

  • 1Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. xwzhan@iccas.ac.cn

Advanced Materials (Deerfield Beach, Fla.)
|December 15, 2010
PubMed
Summary

Rylene diimide materials offer excellent stability and electron mobility for organic electronics. This review highlights recent advancements in perylene- and naphthalene-diimide small molecules and polymers for high-performance transistors and solar cells.

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds
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Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds

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A Simple and Scalable Fabrication Method for Organic Electronic Devices on Textiles
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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

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Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds
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Area of Science:

  • Organic electronics
  • Materials science
  • Polymer chemistry

Background:

  • Organic electron-transporting materials are crucial for devices like organic photovoltaic cells and field-effect transistors.
  • Rylene diimides are a stable and versatile class of polycyclic aromatic electron-transport materials.

Purpose of the Study:

  • To review and analyze recent developments in high-electron-mobility diimides.
  • Focus on rylene- and related aromatic core-based materials, specifically perylene- and naphthalene-diimide small molecules and polymers.

Main Methods:

  • Literature review and analysis of recent research.
  • Focus on materials with high electron mobility for organic electronics applications.

Main Results:

  • Rylene diimides exhibit excellent thermal and oxidative stability.
  • Perylene- and naphthalene-diimide based small molecules and polymers show high electron mobilities.
  • These materials are promising for high-performance organic field-effect transistors and photovoltaic cells.

Conclusions:

  • Recent advancements have significantly improved the performance of rylene diimide-based organic electronic materials.
  • Perylene- and naphthalene-diimides are key components for next-generation organic electronics.