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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.

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1,3,2-Dioxaborine-based mero-polyanionic dyes: high-extinction NIR-absorbing polymethines.

Vladyslav Polishchuk1, Svitlana Shishkina1, Mykola Shandura1

  • 1Institute of Organic Chemistry, National Academy of Sciences of Ukraine Akademika Kukharya Street 5 Kyiv 02094 Ukraine vlad3ds@gmail.com.

RSC Advances
|June 1, 2026
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Summary

New polymethine dyes with unique electronic structures were synthesized. These mero-polyanionic chromophores show strong near-infrared absorption and fluorescence, offering potential applications in advanced materials.

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Published on: June 10, 2021

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Polymethine dyes are crucial chromophores with diverse applications.
  • Developing dyes with tunable electronic structures and enhanced optical properties is an ongoing challenge.

Purpose of the Study:

  • To synthesize and characterize novel polymethine dyes incorporating meso-cyano-2,2-difluoro-1,3,2-dioxaborine units.
  • To investigate the unique electronic structure combining merocyanine-like and polyanionic characteristics.
  • To evaluate their photophysical properties, including absorption, fluorescence, and photostability.

Main Methods:

  • Synthesis of polymethine dyes with specific donor-acceptor units.
  • Characterization using X-ray crystallography to determine molecular structure.
  • Spectroscopic analysis (UV-Vis absorption, fluorescence) in various solvents.
  • Photostability testing against standard cyanine dyes.

Main Results:

  • Successful synthesis of polymethine dyes with mero-polyanionic chromophores in symmetric and unsymmetric architectures.
  • X-ray analysis revealed non-uniform electron density distribution.
  • Observed strong near-infrared absorption up to 940 nm with high molar absorption coefficients (up to 468,000 M-1 cm-1).
  • Oligomers exhibited strong fluorescence around 800 nm (quantum yields 0.10-0.16) and good photostability.

Conclusions:

  • The synthesized dyes possess an unusual electronic structure combining D-π-A and polyanionic systems.
  • These dyes demonstrate excellent NIR absorption and fluorescence properties with high molar absorptivity.
  • Their photostability is comparable to established cyanine dyes, indicating potential for advanced optical and material applications.