Meso enyne substituted BODIPYs: synthesis, structure and properties

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Boron-dipyrromethene (BODIPY) dyes are widely used in various applications due to their photophysical properties.
• Functionalization of BODIPY core is crucial for tuning their properties and expanding their applications.
• Meso-alkynylated BODIPYs serve as versatile platforms for further chemical modifications.

Purpose of the Study:

• To synthesize novel meso enyne substituted BODIPY dyes.
• To investigate the optical properties of these new BODIPY derivatives.
• To explore the self-assembly behavior and supramolecular structures formed by these compounds.

Main Methods:

• Sonogashira coupling reaction between 8-chloro BODIPY and terminal alkynes.
• Palladium-copper catalyzed hydroalkynylation of meso alkynylated BODIPYs with terminal alkynes.
• Single crystal X-ray diffraction for structural analysis.

Main Results:

• Successful synthesis of a range of meso enyne substituted BODIPYs with diverse substituents.
• Meso enyne substituted BODIPYs exhibit blue-shifted absorption and red-shifted emission compared to their precursors.
• Formation of 1D supramolecular frameworks extending into 3D structures driven by C-Hπ, C-HF hydrogen bonding, and ππ stacking.

Conclusions:

• The developed synthetic strategies provide access to novel enyne-functionalized BODIPY dyes.
• The new BODIPY derivatives possess tunable photophysical properties suitable for advanced applications.
• The compounds demonstrate propensity for forming ordered supramolecular architectures with potential in materials science.