Highly fluorinated benzobisbenzothiophenes.

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Benzobisbenzothiophenes (BBBT) are a class of organic semiconductors with potential applications in electronics.
• Fluorination is a common strategy to tune the electronic properties and solid-state packing of organic molecules.
• Understanding the self-assembly behavior of fluorinated BBBTs is crucial for designing high-performance materials.

Purpose of the Study:

• To develop facile and efficient synthetic routes for highly fluorinated benzobisbenzothiophenes (BBBTs).
• To investigate the impact of peripheral sulfur and fluorine atom arrangements on molecular self-assembly.
• To explore the relationship between molecular structure, crystalline networks, and electronic properties.

Main Methods:

• Expedient synthetic methodologies were employed to access a range of fluorinated BBBT derivatives.
• X-ray crystallography was used to analyze the crystalline structures and identify intermolecular interactions.
• Solid-state electronic properties were measured and correlated with structural features.

Main Results:

• Highly fluorinated BBBTs were synthesized efficiently.
• Defined arrangements of sulfur and fluorine atoms resulted in extensive crystalline networks.
• Close S-F contacts were observed, facilitating edge-to-edge molecular packing.
• Substitution patterns significantly influenced self-assembly and electronic properties.

Conclusions:

• Facile synthetic access to fluorinated BBBTs is achievable.
• The precise arrangement of S and F atoms dictates the formation of specific crystalline networks driven by S-F interactions.
• These findings provide a foundation for designing novel organic electronic materials with tailored properties.