Soluble Twisted Diarenoperylenes: Synthesis, Characterization, and Device Performance

Area of Science:

• Organic Chemistry
• Materials Science
• Solid-State Physics

Background:

• Polycyclic aromatic hydrocarbons (PAHs) are crucial in organic electronics.
• Developing PAHs with efficient charge transport remains a key challenge.
• Functionalization of PAHs can tune their electronic properties and solid-state packing.

Purpose of the Study:

• To synthesize and characterize two new TIPS-ethynyl functionalized PAHs: dibenzo[a,j]perylene (TIPS-DBP) and dinaphtho[a,j]perylene (TIPS-DNP).
• To investigate the charge-transport properties of these novel materials in crystalline form.
• To explore the relationship between molecular structure and charge mobility in twisted PAHs.

Main Methods:

• Synthesis of TIPS-ethynyl functionalized PAHs via established organic chemistry routes.
• Crystallization and structural characterization using X-ray diffraction.
• Measurement of charge-carrier mobility using field-effect transistor devices.

Main Results:

• Successful synthesis and characterization of TIPS-DBP and TIPS-DNP.
• Demonstrated formation of one-dimensional charge-transport systems with short intermolecular C-C contacts.
• Achieved high hole mobility in TIPS-DBP crystals (up to 0.17 cm² V⁻¹s⁻¹) and TIPS-DNP crystals (up to 0.74 cm² V⁻¹s⁻¹).

Conclusions:

• TIPS-ethynyl functionalization enables the formation of efficient charge-transport pathways in twisted PAHs.
• TIPS-DNP exhibits exceptionally high hole mobility, highlighting its potential for organic electronic applications.
• These findings contribute to the design of high-performance organic semiconductor materials.