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Ready BODIPY-Tagging of Carboxylic Acids
José G Becerra-González1, Sergio E Solorio-Hernández1, Dante G Zacarías-Gómez1
1Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, Guanajuato, Guanajuato 36050, Mexico.
The Journal of Organic Chemistry
|May 11, 2026
Summary
Meso-aminoBODIPY derivatives are efficient for tagging carboxylic acids using Steglich amidation. These new fluorescent compounds exhibit significant spectral shifts and high quantum yields for sensing applications.
Area of Science:
- Organic Chemistry
- Fluorescent Probes
- Materials Science
Background:
- BODIPY dyes are widely used fluorescent probes.
- Functionalization of BODIPY dyes is crucial for tuning their photophysical properties.
- Carboxylic acid tagging is essential in various chemical and biological applications.
Purpose of the Study:
- To develop a robust method for synthesizing novel meso-aminoBODIPY amide derivatives.
- To investigate the photophysical properties of these new derivatives.
- To explore their potential applications in fluorescence sensing.
Main Methods:
- Utilized the Steglich amidation protocol (DCC, DMAP) at room temperature.
- Synthesized 18 new derivatives from unsubstituted meso-aminoBODIPY.
- Synthesized 4 additional analogues from functionalized amino derivatives.
Main Results:
- Achieved moderate-to-high yields (30-86%) for the synthesized derivatives.
- Demonstrated excellent functional group tolerance during the amidation reaction.
- Observed a significant bathochromic shift (60-80 nm) in absorption and emission spectra.
- Maintained high fluorescence quantum yields and short lifetimes.
Conclusions:
- Meso-aminoBODIPY derivatives are stable and efficient starting materials for carboxylic acid tagging.
- The developed amidation method is versatile and tolerant of various functional groups.
- The resulting BODIPY amides possess tunable photophysical properties suitable for fluorescence sensing applications.
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