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

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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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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Diazonium Group Substitution: –OH and –H01:19

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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.
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Controlling the Isomerization Rate of an Azo-BF2 Switch Using Aggregation.

Hai Qian1, Yu-Ying Wang2, Dong-Sheng Guo2

  • 1Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.

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|January 11, 2017
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Researchers developed a new light-activated molecule that self-assembles. This aggregation allows precise control over its switching speed, enabling tunable molecular switches with half-lives from seconds to days.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Electronics
  • Photochemistry

Background:

  • Molecular switches are crucial for developing advanced materials and devices.
  • Controlling the switching dynamics of molecular switches is a significant challenge.
  • Self-assembly offers a promising route to modulate molecular properties.

Purpose of the Study:

  • To synthesize and characterize a novel visible-light activated azo-BF2 switch.
  • To investigate the influence of self-aggregation on the switching properties of the molecule.
  • To demonstrate the active tuning of the thermal relaxation half-life.

Main Methods:

  • Synthesis of a novel azo-BF2 molecule with a phenanthridinyl π-system.
  • Characterization of switching properties as a function of concentration.
  • Analysis of self-aggregation behavior through π-π interactions.
  • Measurement of Z → E thermal isomerization rates and half-lives.

Main Results:

  • Successful synthesis of the visible-light activated azo-BF2 switch.
  • Demonstration of self-aggregation driven by π-π interactions.
  • Correlation between the degree of aggregation and the Z → E thermal isomerization rate.
  • Tunable thermal relaxation half-life ranging from seconds to days.

Conclusions:

  • The synthesized azo-BF2 switch exhibits concentration-dependent self-aggregation.
  • Self-aggregation effectively modulates the thermal isomerization rate, enabling tunable switching.
  • This work presents a novel strategy for designing responsive molecular switches with controllable dynamics.