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BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies
Andrei V Zaitsev1, Sergey S Kiselev1, Alexander F Smol'yakov1,2
1A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, bld. 1 Vavilova St., 119334 Moscow, Russian Federation. olshevsk@ineos.ac.ru.
Organic & Biomolecular Chemistry
|May 2, 2023
Summary
Researchers developed a new method to create boron-enriched BODIPY dyes by attaching carborane clusters. This functionalization enhances the optical properties of these important fluorescent molecules.
Area of Science:
- Organic Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Boron-dipyrromethene (BODIPY) dyes are widely used due to their strong fluorescence and photostability.
- Carboranes are unique boron-rich clusters with potential applications in medicine and materials science.
- Functionalization of BODIPYs with carboranes can lead to novel materials with tailored optoelectronic properties.
Purpose of the Study:
- To develop an efficient synthetic route for 3,5-dicarborane-substituted BODIPY conjugates.
- To investigate the impact of carborane substitution on the photophysical properties of BODIPYs.
- To explore the potential for further functionalization of carborane-BODIPY conjugates.
Main Methods:
- Nucleophilic substitution reactions using neutral and anionic carborane S-nucleophiles.
- Functionalization of 3,5-dibromo-8-pentafluorophenyl-BODIPY.
- SNAr reactions on the meso-pentafluorophenyl substituent.
- Spectroscopic analysis (absorption, fluorescence) and quantum yield determination.
- X-ray crystallography for structural elucidation.
- Density Functional Theory (DFT) calculations for electronic and geometric analysis.
Main Results:
- Successful synthesis of 3,5-dicarborane-substituted BODIPYs in good yields.
- Demonstration of facile introduction of a third carborane cluster via SNAr reactions.
- Analysis of the influence of carborane substitution on absorption/fluorescence spectra and quantum yields.
- Structural characterization of key BODIPY derivatives.
- DFT studies provided insights into electronic structures and molecular geometries.
Conclusions:
- An efficient method for preparing carborane-BODIPY conjugates was established.
- Carborane substitution significantly modulates the photophysical properties of BODIPYs.
- The developed compounds represent novel boron-enriched fluorescent materials.
- The synthetic strategy allows for further diversification and tuning of BODIPY properties.
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