BOSHPY Fluorophores: BODIPY Analogues with Single Atom Controlled Aggregation

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Porphyrazines and BODIPY dyes are important classes of fluorescent molecules.
• Controlling molecular aggregation is crucial for tuning photophysical properties.
• Semihemiporphyrazines offer a versatile scaffold for developing new functional dyes.

Purpose of the Study:

• To synthesize novel fluorescent compounds based on the semihemiporphyrazine core.
• To investigate the aggregation behavior of these compounds and its dependence on peripheral substituents.
• To explore the potential of these compounds as fluorescent materials, particularly in their aggregated states.

Main Methods:

• Reaction of diiminoisoindoline and iminoxoisoindoline with aminoazoles to form bidentate chelates.
• Complexation of chelates with BF3 to yield difluoroboron semihemiporphyrazines (BOSHPYs).
• Spectroscopic analysis (UV-Vis, fluorescence) to characterize the compounds and their aggregation properties.

Main Results:

• Successful synthesis of novel difluoroboron semihemiporphyrazines (BOSHPYs).
• Demonstrated that the aggregation mode (H or J) is controlled by peripheral oxygen or nitrogen atoms.
• Observed that imine-terminated BOSHPYs retain fluorescence in aggregated states.

Conclusions:

• Difluoroboron semihemiporphyrazines represent a new class of fluorescent dyes with tunable aggregation.
• Peripheral atom modification offers a strategy to control supramolecular assembly and photophysical properties.
• The fluorescence retention in aggregated states makes BOSHPYs promising for applications requiring solid-state emission.