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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
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.
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...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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.
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...
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...

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Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications
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Structure-Reactivity Relationships Applied to Diazonium-Based Surface Functionalization: Toward Tunable Redox

Elie Bou Rahhal1, Talia Bsaibess1, Yanis Ntalagana1

  • 1MOLTECH-Anjou, SFR MATRIX, Université Angers, CNRS, Angers F-49000, France.

Langmuir : the ACS Journal of Surfaces and Colloids
|May 7, 2026
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Summary

Rational molecular design with alkyl spacers enables controlled surface modification. This approach overcomes limitations in diazonium salt chemistry, allowing precise tuning of mixed organic monolayers for advanced materials.

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Area of Science:

  • Materials Chemistry
  • Surface Science
  • Organic Electronics

Background:

  • Precise engineering of surface-bound organic layers is crucial for materials chemistry.
  • Diazonium salt electroreduction creates robust films but lacks control over coverage and dynamic exchange, leading to multilayer growth.
  • Tuning composition in mixed monolayers is complicated by uncontrolled film thickness.

Purpose of the Study:

  • To demonstrate how rational molecular design, using extended alkyl spacers, overcomes limitations in diazonium-based surface modification.
  • To enable controlled coimmobilization of functional and diluent species in mixed monolayers.
  • To promote confinement of film growth within the monolayer regime.

Main Methods:

  • Utilized diazonium salt electroreduction for surface modification.
  • Incorporated extended alkyl spacers (C12) into diazonium precursors.
  • Employed TEMPO as a model redox-active motif for electrochemical characterization.
  • Compared mixed layers with and without alkyl spacers.

Main Results:

  • Extended alkyl spacers suppressed overgrowth, confining film growth to the monolayer regime.
  • Predictable tuning of redox unit surface density was achieved by adjusting solution composition.
  • The presence of linkers influenced the interfacial arrangement of grafted species.
  • Controlled coimmobilization of functional and diluent species was demonstrated.

Conclusions:

  • Rational molecular design with extended alkyl spacers provides clear design principles for controlled assembly of multifunctional organic interfaces.
  • This approach overcomes limitations in diazonium-based surface modification, enabling precise control over monolayer composition and structure.
  • Established new insights into structure-reactivity relationships for diazonium-mediated surface functionalization.