Engineering perfluoroarenes for enhanced molecular barrier effect and chirality transfer in solutions

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Organic Electronics

Background:

• Noncovalent forces significantly influence material photophysical properties.
• Arene-perfluoroarene (AP) interactions, a type of π-hole/π interaction, offer unique directionality for supramolecular assembly.
• Designing novel luminescent materials requires precise control over molecular interactions.

Purpose of the Study:

• To develop an amination engineering protocol for creating a perfluoroarene library.
• To investigate the role of perfluoroarenes as molecular barriers in luminescent assemblies.
• To explore the transfer of chirality and the creation of circularly polarized luminescence.

Main Methods:

• Synthesis of a perfluoroarene library based on an octafluoronaphthalene skeleton.
• Assembly of perfluoroarenes with perylene building units in diluted solutions.
• Analysis of structure-property correlations, including steric effects and hydrophobicity.

Main Results:

• Perfluoroarenes effectively act as molecular barriers, enhancing luminescence in solution-based assemblies.
• Steric effects, hydrophobicity, and aromatic pendants are key factors for boosting the molecular barrier effect.
• Chirality transfer from perfluoroarenes to perylene induced chiral microstructures and tailored circularly polarized luminescence.

Conclusions:

• This work expands the possibilities for molecular engineering in noncovalently bonded luminescent materials.
• Structure-property correlations were clearly established, guiding future material design.
• Applications in water-resistant luminescent inks for displays and anti-counterfeiting were demonstrated.