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Related Concept Videos

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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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, or cyano...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Published on: August 22, 2018

Three-stage binary switching of azoaromatic polybase.

Ho Yong Lee1, András Olasz, Chun-Hsing Chen

  • 1Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.

Organic Letters
|December 5, 2012
PubMed
Summary
This summary is machine-generated.

A novel azoaniline-based polybase enables three-stage binary switching. Its unique protonation-dependent optical response, distinct from typical behaviors, was confirmed through experimental and computational analyses.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Azo-based polymers offer tunable optical properties.
  • Protonation-responsive materials are crucial for sensors and switches.
  • Understanding molecular mechanisms behind optical changes is key for material design.

Purpose of the Study:

  • To design and synthesize an azoaniline-based polybase capable of multi-stage switching.
  • To investigate the unusual optical response of the polybase upon protonation.
  • To elucidate the molecular mechanism governing the observed optical behavior.

Main Methods:

  • Synthesis of azoaniline-based polybase (1).
  • Spectroscopic analysis (UV-Vis, fluorescence) of protonation states ([1·H]+, [1·2H]2+).
  • Density Functional Theory (DFT) computational modeling.

Main Results:

  • Achieved an OFF-ON-OFF three-stage binary switching behavior.
  • Observed indistinguishable optical properties for 1 and [1·2H]2+ but distinct from [1·H]+.
  • Demonstrated an unusual bell-shaped optical response curve as a function of protonation.
  • Unraveled the molecular mechanism using combined experimental and DFT data.

Conclusions:

  • The azoaniline-based polybase exhibits controllable multi-stage switching.
  • The unique protonation-dependent optical response is attributed to specific molecular interactions and electronic changes.
  • This study provides insights into designing advanced responsive materials.