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Conventional BODIPY Conjugates for Live-Cell Super-Resolution Microscopy and Single-Molecule Tracking
Published on: June 8, 2020
Highly substituted Bodipy dyes with spectroscopic features sensitive to the environment
Thomas Bura1, Pascal Retailleau, Gilles Ulrich
1Laboratoire de Chimie Moléculaire et Spectroscopies Avancées (LCOSA), ECPM, CNRS, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
The Journal of Organic Chemistry
|January 20, 2011
Summary
A new method synthesizes butterfly-shaped difluoroboradiaza-s-indacenes, offering tunable optical properties. These novel dyes exhibit strong absorption and emission, with potential applications in pH sensing.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Difluoroboradiaza-s-indacenes (Bodipy) are versatile fluorophores.
- Developing synthetic routes for tailored Bodipy derivatives is crucial for advanced applications.
Purpose of the Study:
- To develop a general synthetic method for butterfly-shaped difluoroboradiaza-s-indacenes.
- To investigate structure-property relationships for tuning optical characteristics.
- To explore their potential as pH sensors.
Main Methods:
- Sequential Knoevenagel reactions using substituted benzaldehydes.
- Synthesis of A(2)B(2) and ABCD derivatives from a tetramethyl-substituted Bodipy precursor.
- Stepwise functionalization including methylation and alkylation.
- Spectroscopic characterization (absorption, emission, quantum yield, lifetime).
Main Results:
- Successful synthesis of butterfly-shaped difluoroboradiaza-s-indacenes with diverse substituents.
- Absorption wavelengths from 573-718 nm and emission from 585-800 nm.
- High quantum yields and nanosecond excited state lifetimes indicating singlet emission.
- pH-dependent optical properties due to amino and phenol groups.
- Demonstration of a three-color ratiometric pH sensor.
Conclusions:
- A versatile synthetic strategy for butterfly-shaped difluoroboradiaza-s-indacenes has been established.
- The developed dyes exhibit excellent photophysical properties and tunable characteristics.
- These compounds show promise for applications in sensing, particularly as ratiometric pH sensors.
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