Curcuminoid-BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage.

Area of Science:

• Coordination Chemistry
• Organic Synthesis
• Materials Science

Background:

• Curcumin derivatives are known for their versatile chemical properties and biological activities.
• Difluoroboron complexes offer unique photophysical properties, making them attractive for various applications.
• Developing efficient synthetic routes and understanding the properties of novel curcumin-based difluoroboron complexes is of significant interest.

Purpose of the Study:

• To synthesize novel difluoroboron complexes derived from substituted alkyne-containing curcuminoids.
• To investigate the photophysical properties of the synthesized complexes as fluorescent dyes.
• To establish a reliable method for the hydrolysis of the difluoroboron group in these complexes.

Main Methods:

• Optimized reaction pathway for the synthesis of eight difluoroboron curcumin derivatives.
• Characterization of synthesized complexes for yield and purity.
• Investigation of fluorescent properties.
• Development of a hydrolysis strategy using aqueous methanol with sodium hydroxide or triethylamine.

Main Results:

• Eight novel difluoroboron complexes of curcumin derivatives were successfully synthesized.
• The synthesis achieved high yields (up to 98%) and high purities.
• The fluorescent properties of the complexes were systematically investigated.
• An effective hydrolysis strategy for the difluoroboron group was established.

Conclusions:

• The optimized synthesis provides a reliable route to novel difluoroboron curcumin complexes.
• These complexes exhibit promising characteristics as fluorescent dyes.
• The developed hydrolysis method offers a pathway for further functionalization or modification of the complexes.