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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.
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...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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.

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Related Experiment Video

Updated: May 29, 2026

Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids
09:04

Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids

Published on: September 21, 2017

An azo-based PNA monomer: synthesis and spectroscopic study.

Mohamed E Moustafa1, Robert H E Hudson

  • 1Department of Chemistry, The University of Western Ontario, London, Ontario, Canada.

Nucleosides, Nucleotides & Nucleic Acids
|September 10, 2011
PubMed
Summary

Researchers synthesized a novel peptide nucleic acid (PNA) monomer with an azobenzene base surrogate. This PNA monomer can quench fluorescence and act as an energy transfer partner in molecular beacons.

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Area of Science:

  • Synthetic organic chemistry
  • Biochemistry
  • Materials science

Background:

  • Peptide nucleic acids (PNAs) are DNA/RNA mimics with unique binding properties.
  • Azobenzene moieties can be incorporated into biomolecules for photoresponsive applications.
  • Fluorescence quenching and Förster resonance energy transfer (FRET) are key mechanisms in molecular sensing.

Purpose of the Study:

  • To synthesize and characterize a novel PNA monomer incorporating an azobenzene group.
  • To evaluate the photophysical properties of the azobenzene-PNA monomer.
  • To demonstrate the utility of the monomer in a PNA-based molecular beacon system.

Main Methods:

  • Full synthetic procedures for the azobenzene-PNA monomer.
  • Photospectroscopic characterization techniques.
  • Assembly of a PNA-based molecular beacon incorporating the novel monomer.

Main Results:

  • Successful synthesis and full characterization of the azobenzene-PNA monomer.
  • Demonstrated ability of the monomer to quench fluorescence of fluorescein and pyrene.
  • Established the monomer as a competent FRET partner in a PNA molecular beacon.

Conclusions:

  • A novel azobenzene-containing PNA monomer was developed.
  • The monomer exhibits useful photophysical properties for fluorescence modulation.
  • This PNA monomer is suitable for developing advanced molecular sensing and imaging tools.