BNB-doped phenalenyls - aromaticity switch upon one-electron reduction.

Area of Science:

• Organic Chemistry
• Materials Science
• Photophysics

Background:

• Phenalenyls are a class of polycyclic aromatic hydrocarbons with unique electronic properties.
• Developing novel luminescent and robust organic materials is crucial for advanced applications.

Purpose of the Study:

• To synthesize and characterize fully aromatic, luminescent, and robust BNB-doped phenalenyls.
• To investigate the electronic and photophysical properties of these novel compounds.
• To explore the structural changes upon reduction using theoretical methods.

Main Methods:

• Chemical synthesis of BNB-doped phenalenyls.
• Spectroscopic characterization (UV-Vis absorption, fluorescence).
• Electrochemical measurements (reduction potential).
• Density Functional Theory (DFT) calculations.

Main Results:

• Successfully prepared fully aromatic, luminescent, and robust BNB-doped phenalenyls.
• B-Fluoromesityl-substitution resulted in narrow-range fluorescence and increased reduction potential.
• Theoretical studies confirmed an intramolecular aromaticity switch upon one-electron reduction.

Conclusions:

• BNB-doped phenalenyls represent a new class of functional organic materials.
• The observed aromaticity switch offers potential for redox-switchable optical properties.
• These findings open avenues for designing advanced luminescent and electronic materials.