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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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Highly Fluorescent Dianionic Polymethines with a 1,3,2-Dioxaborine Core.

Vladyslav Polishchuk¹, Andrii Kulinich¹, Eduard Rusanov¹

¹Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska Str., 02094 Kyiv, Ukraine.

The Journal of Organic Chemistry

|March 17, 2021

Summary

Researchers developed novel dianionic cyanine dyes featuring a difluoroboron β-diketonate core. These bright fluorophores exhibit tunable absorption from 530-770 nm and high quantum yields for visible and near-infrared applications.

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Published on: October 24, 2017

Area of Science:

Organic Chemistry
Materials Science
Photophysics

Background:

Difluoroboron β-diketonate motifs are increasingly utilized in synthesizing polymethine fluorophores.
Polymethine dyes are crucial for applications spanning the visible and near-infrared (NIR) spectral regions.

Purpose of the Study:

To synthesize and characterize a new series of dianionic cyanine dyes with a central dioxaborine ring.
To investigate the spectral properties, including absorption and fluorescence, of these novel dyes with varying electron-acceptor terminal groups.

Main Methods:

Synthesis of A¹-π-A-π-A¹ type dianionic cyanine dyes incorporating a central dioxaborine ring (A).
Spectroscopic analysis (absorption and fluorescence) to determine photophysical properties.
Evaluation of solvatochromism and quantum yields in various solvents.

Main Results:

Intensive absorption bands (molar extinction up to 380,000 M^-1 cm^-1) were observed in the 530-770 nm range, tunable by terminal groups.
Absorption and fluorescence spectra showed near mirror-image symmetry with minimal solvatochromism, except in methanol.
High fluorescence quantum yields were achieved, up to 92% in the visible range and 18-37% for NIR dyes in DMF.

Conclusions:

The synthesized dianionic cyanine dyes offer tunable photophysical properties for visible and NIR applications.
The difluoroboron β-diketonate core enables the creation of highly emissive and stable fluorophores.
These dyes represent promising candidates for advanced optical and imaging technologies.