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Published on: June 10, 2021
Boron difluoride complexes of 3-hydroxyflavone derivatives: efficient bioinspired dyes for solution and solid-state
Anthony D'Aléo1, Frédéric Fages
1Aix Marseille Université, CINaM UMR 7325 CNRS, Campus de Luminy, Case 913, 13288 Marseille, France. daleo@cinam.univ-mrs.fr
Summary
Six novel boron difluoride dyes derived from 3-hydroxyflavone exhibit bright emission in solution and solid states. Their photophysical properties, influenced by donor-acceptor strength and molecular packing, offer insights into advanced luminescent materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- 3-hydroxyflavone derivatives are known for their fluorescent properties.
- Boron difluoride (BF2) complexation can significantly alter the photophysical characteristics of organic molecules.
- Understanding structure-property relationships in luminescent dyes is crucial for developing new optical materials.
Purpose of the Study:
- To synthesize and characterize a series of boron difluoride complexes of 3-hydroxyflavone derivatives.
- To investigate the effect of boron difluoride complexation on the emission properties of these dyes in solution and solid states.
- To explore the influence of substituent variations on the photophysical behavior and solid-state emission.
Main Methods:
- Simple synthesis of six boron difluoride complexes of 3-hydroxyflavone derivatives.
- Spectroscopic analysis (UV-Vis absorption and fluorescence emission) in solution.
- Investigation of solid-state emission properties.
- Analysis of molecular packing and electronic properties.
Main Results:
- The synthesized dyes displayed bright visible emission with quantum yields up to unity in solution.
- Boron difluoride complexation induced donor-acceptor character, shifting emission to the visible spectrum.
- Emission intensity in the solid state was quenched compared to solution, attributed to π-stacking, packing, and electronic effects.
- Molecular packing arrangement was found to be dependent on the substituents of the 3-hydroxyflavone derivatives.
Conclusions:
- Boron difluoride complexes of 3-hydroxyflavone are promising luminescent materials with tunable emission.
- The interplay between molecular structure, electronic properties, and solid-state packing governs their photophysical behavior.
- These findings provide a foundation for designing novel fluorescent dyes with tailored optical properties for various applications.
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