Borylated perylenediimide: self-assembly, photophysics and sensing application

Area of Science:

• Materials Science
• Supramolecular Chemistry
• Organic Electronics

Background:

• Perylenediimide (PDI) derivatives are widely studied for their optical and electronic properties.
• Controlling self-aggregation and solubility is crucial for developing functional PDI-based materials.
• Triarylboranes (TABs) are known for their electron-deficient nature and ability to influence molecular interactions.

Purpose of the Study:

• To design and synthesize a novel Triarylboryl appended perylenediimide (PDI-TAB) molecule.
• To investigate the impact of TAB incorporation on PDI solubility, self-aggregation, and optical properties.
• To explore the controlled self-assembly of PDI-TAB and its application as a fluorogenic sensor for fluoride anions.

Main Methods:

• Chemical synthesis of PDI-TAB.
• Solubility and fluorescence spectroscopy measurements.
• Controlled precipitation and solution processing for self-assembly.
• Powder X-ray Diffraction (PXRD) analysis.
• Theoretical calculations to elucidate sensing mechanism.

Main Results:

• Successful synthesis of PDI-TAB, exhibiting enhanced solubility and reduced self-aggregation.
• Tunable fluorescence emission (red, yellow, green) achieved by modulating PDI-TAB concentration.
• Controlled formation of self-assembled structures, including finite fibers and flexible 1D fibers, depending on experimental conditions.
• PXRD confirmed consistent molecular organization in different self-assembled morphologies.
• PDI-TAB demonstrated selective fluorogenic sensing of toxic fluoride anions.

Conclusions:

• PDI-TAB is a versatile material with tunable photophysical properties and controllable self-assembly.
• The incorporation of triarylboranes effectively enhances solubility and modulates aggregation behavior.
• PDI-TAB shows significant potential as a selective and sensitive fluorogenic sensor for fluoride detection.