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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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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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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Preparation of Epoxides03:00

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Preparation of Alkynes: Alkylation Reaction02:27

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Triazole-Based Functionalized Olygo(Arylene Ethynylene)s-Synthesis and Properties.

Anastasia I Govdi1, Vasiliy V Menchikov1, Ilya E Kolesnikov2

  • 1Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.

Molecules (Basel, Switzerland)
|December 11, 2025
PubMed
Summary

New oligo(arylene ethynylene)s (OAEs) were synthesized using the retro-Favorskii reaction. These OAEs exhibit tunable fluorescence properties, with aggregate-induced emission enhancement observed in aqueous organic solutions.

Keywords:
1,2,3-triazolesSonogashira cross-couplingaggregation-induced emission enhancementazide–alkyne cycloadditionfluorescenceolygo(arylene ethynylene)s

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Oligo(arylene ethynylene)s (OAEs) are conjugated polymers with potential applications in organic electronics and photonics.
  • The synthesis and photophysical properties of OAEs are of significant interest for developing new functional materials.

Purpose of the Study:

  • To synthesize novel OAEs incorporating 1,2,3-triazole units and explore their fluorescence characteristics.
  • To investigate the effect of substituents and solvent polarity on the emission properties of these OAEs.
  • To study the phenomenon of aggregate-induced emission enhancement (AIEE) in aqueous organic media.

Main Methods:

  • Synthesis of OAEs via the retro-Favorskii reaction, utilizing 4,5-(diethynylaryl)-1,2,3-triazoles.
  • Characterization of synthesized OAEs using spectroscopic techniques (fluorescence spectroscopy).
  • Investigation of solvent effects on emission spectra and quantum yields in various organic solvents and aqueous mixtures.
  • Dynamic light scattering (DLS) to study aggregate formation.

Main Results:

  • OAEs with trimethoxyphenyl substituents showed high fluorescence quantum yields (up to 88%) in THF.
  • Minimal solvent polarity effect on emission for trimethoxyphenyl derivatives.
  • Significant red shifts and hypochromic effects observed for OAEs with para-dimethylaminophenyl groups in polar solvents.
  • Aggregate-induced emission enhancement (AIEE) observed in aqueous organic solutions, particularly in DMSO/water mixtures.
  • DLS confirmed the formation of nanoscale aggregates in aqueous organic media.

Conclusions:

  • The retro-Favorskii reaction is an effective method for synthesizing novel OAEs with tunable photophysical properties.
  • The electronic nature of substituents significantly influences the emission behavior of OAEs in different solvent environments.
  • The synthesized OAEs demonstrate potential for applications where aggregate formation leads to enhanced fluorescence, such as in sensing or imaging.