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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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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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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.4K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
3.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.9K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

5.1K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
5.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Dicyano-Substituted Diazaacenes.

Matthias Müller1, Stella S Beglaryan1, Silke Koser1

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

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 16, 2017
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel dicyano-substituted azaacenes with three to six rings. These organic semiconductors exhibit n-type behavior, demonstrating potential for use in organic field-effect transistors.

Keywords:
Pd-catalyzed couplingazaacenescyanidesdensity functional calculationsn-type semiconductors

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Organic Electronics

Background:

  • Azaacenes are nitrogen-containing polycyclic aromatic hydrocarbons with unique electronic properties.
  • Dicyano substitution can significantly tune the electronic and optical characteristics of organic molecules.

Purpose of the Study:

  • To synthesize and characterize novel 2,3-dicyano-substituted azaacenes with varying numbers of fused rings.
  • To investigate the structural properties and solid-state packing of these new compounds.
  • To evaluate their potential as n-type semiconductors in organic electronics.

Main Methods:

  • Palladium-catalyzed coupling reactions were employed to construct the azaacene frameworks.
  • Synthesis involved coupling diamino-bis(tri-isopropylsilylethynyl) precursors with dibromophthalonitrile or dibromonaphthyldicarbonitrile.
  • Oxidation of intermediate dihydrodiazaacenes using manganese dioxide or lead dioxide yielded the final products.

Main Results:

  • A series of 2,3-dicyano-substituted azaacenes with three to six annelated rings were successfully synthesized.
  • Crystallographic analysis revealed diverse packing motifs, including isolated pairs, stacks, and brick-wall arrangements.
  • Proof-of-concept organic field-effect transistors demonstrated n-type semiconducting behavior with mobilities up to 7×10⁻³ cm² V⁻¹ s⁻¹.

Conclusions:

  • The developed synthetic route provides access to a new class of dicyano-substituted azaacenes.
  • The structural diversity and observed n-type semiconducting properties highlight the potential of these molecules for organic electronic applications.