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Updated: Jun 15, 2026
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Conventional BODIPY Conjugates for Live-Cell Super-Resolution Microscopy and Single-Molecule Tracking
Published on: June 8, 2020
Boron asymmetry in a BODIPY derivative
Alexandre Haefele1, Chantal Zedde, Pascal Retailleau
1LCOSA, ECPM, UMR 7515, CNRS-UdS, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
Organic Letters
|March 19, 2010
Summary
Chiral boradiazaindacene (BODIPY) fluorophores with central boron chirality were synthesized and resolved. Modifications to the BODIPY core created a stable hydrogen bond, confirming the persistence of both enantiomers.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Boron-containing compounds, particularly boradiazaindacene (BODIPY) fluorophores, are crucial in various chemical and material applications.
- Chirality in molecular design is essential for developing advanced functional materials and pharmaceuticals.
- Controlling and understanding chirality in complex organic molecules remains a significant challenge.
Purpose of the Study:
- To synthesize a novel chiral boradiazaindacene (BODIPY) fluorophore with chirality centered on the boron atom.
- To resolve the synthesized racemate into its individual enantiomers.
- To investigate the structural and conformational stability of the chiral BODIPY system.
Main Methods:
- Synthesis of a novel boradiazaindacene (BODIPY) derivative featuring a chiral center at the boron atom.
- Racemic resolution using chiral chromatography techniques.
- Chemical modification of the BODIPY core via oxidation of a methyl group to a carboxaldehyde.
- Structural characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray diffraction.
- Confirmation of enantiomeric persistence using chiral High-Performance Liquid Chromatography (HPLC) and Circular Dichroism (CD) spectroscopy.
Main Results:
- Successful synthesis and resolution of a chiral BODIPY fluorophore with boron chirality.
- Introduction of a carboxaldehyde group through oxidation, leading to dissymetrization of the BODIPY core.
- Evidence of a stable intramolecular hydrogen bond between the aldehyde proton and a fluorine atom on the boron, confirmed by NMR and X-ray diffraction.
- Demonstration of the persistence of both enantiomers under the applied experimental conditions.
Conclusions:
- The study presents a novel chiral BODIPY fluorophore with chirality precisely located at the central boron atom.
- The synthesized molecule exhibits a stable intramolecular hydrogen bond, contributing to its structural integrity.
- The successful resolution and confirmation of enantiomeric persistence open avenues for applications requiring chiral boron-based fluorescent materials.
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