A Cyclic tris-BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as...

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Dithienopyrrole embedded macrocycles offer unique structural and electronic properties.
• Boron-dipyrromethene (BODIPY) dyes are known for their photophysical characteristics.
• Developing novel contrast agents for photoacoustic imaging is crucial for biomedical applications.

Purpose of the Study:

• To synthesize a rigid dithienopyrrole embedded dodecaphyrin and its tris-BODIPY complex.
• To investigate the structural and optical properties of the synthesized compounds.
• To evaluate the potential of the tris-BODIPY complex as a photoacoustic imaging contrast agent.

Main Methods:

• Synthesis of dodecaphyrin and tris-BODIPY complex.
• Density Functional Theory (DFT) analysis for structural elucidation.
• UV-Vis absorption spectroscopy to determine optical properties.
• Evaluation of nonfluorescent characteristics for imaging applications.

Main Results:

• A rigid dithienopyrrole embedded dodecaphyrin and its tris-BODIPY complex were successfully synthesized.
• DFT analysis revealed a "ruffled" structure for dodecaphyrin and a "saddle-shaped" structure for tris-BODIPY.
• The tris-BODIPY complex exhibited a significant red-shift in absorption (ca. 115 nm) into the NIR-I region due to increased conjugation.
• The compound demonstrated nonfluorescent characteristics, essential for photoacoustic imaging.

Conclusions:

• The synthesized tris-BODIPY complex possesses favorable optical properties for photoacoustic imaging.
• Its strong absorption in the NIR-I region and nonfluorescent nature make it an efficient contrast agent.
• This study presents a promising new material for advanced biomedical imaging techniques.