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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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New Design Strategy Toward NIR I Xanthene-Based Dyes.

Ishanka Rajapaksha¹, Hao Chang¹, Yao Xiong²

¹Department of Chemistry, Mississippi State University, Hand Lab 1115, Mississippi State, Mississippi 39762, United States.

The Journal of Organic Chemistry

|August 25, 2020

Summary

Researchers developed novel far-red to near-infrared xanthene-based dyes using Suzuki coupling. These dyes, when activated, exhibit strong fluorescence and can be used to create sensitive probes for detecting fluoride ions in water.

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Published on: January 25, 2020

Area of Science:

Organic Chemistry
Materials Science
Analytical Chemistry

Background:

Xanthene-based dyes are crucial for various optical applications.
Developing far-red to near-infrared (NIR) emitting dyes is essential for advanced imaging and sensing.
Efficient synthetic strategies for NIR dyes are in high demand.

Purpose of the Study:

To report an effective design strategy and efficient synthetic route for xanthene-based far-red to NIR dyes.
To synthesize and characterize novel pyrrole and indole-functionalized xanthene dyes.
To evaluate the potential of these dyes as fluorescent probes, including a fluoride ion sensor.

Main Methods:

Suzuki cross-coupling reaction between fluorescein ditriflate and pyrrole/indole moieties.
Acid-catalyzed ring-opening of nonfluorescent closed dye forms to fluorescent open forms.
Spectroscopic characterization (absorption and emission maxima) of the synthesized dyes.
Fabrication and testing of a fluoride ion probe using a silyl ester receptor.

Main Results:

Successfully synthesized xanthene-based dyes with absorption/emission maxima in the far-red to NIR region (665-719 nm).
Achieved efficient ring-opening to fluorescent forms (3C and 3D) from nonfluorescent precursors (2C and 2D).
Developed a turn-off fluoride ion probe from dye 3C that shows high sensitivity to fluoride, carbonate, and acetate ions.

Conclusions:

The reported design strategy provides an efficient route to far-red to NIR xanthene dyes.
The synthesized dyes exhibit desirable photophysical properties for potential applications.
The developed probe demonstrates excellent selectivity and sensitivity for detecting fluoride ions in aqueous media.