Liquid-Crystalline Naphthalene and Perylene Bisimides with a D2-?2-A Architecture for High-Mobility Organic Field-Effect Transistors

We designed and synthesized four naphthalene and perylene bisimide-based imidazole-containing liquid-crystalline (NI and PI) derivatives based on a donor-pi-acceptor-pi-donor (D2-pi 2-A) architecture. These compounds bear 10 flexible peripheral chains to ensure liquid crystallinity and solution processability making them suitable to use as organic semi-conductors. All four compounds stabilized different columnar phases. Higher thermal stability and lower band gaps were also observed in both NI and PI derivatives. NI derivatives showed larger Stokes shifts, while PI derivatives exhibited very high molar extinction coefficients. Two solution-processable liquid-crystalline compounds (NI-12 and PI-12) were utilized for the fabrication of organic field-effect transistors, exhibiting a hole mobility of 1.99 cm2/V center dot s for NI-12 and 0.63 cm2/V center dot s for PI-12 derivatives at room temperature in normal air conditions.

Automated summary

We designed and synthesized four liquid-crystalline derivatives based on naphthalene and perylene bisimide with imidazole-containing groups. These compounds with 10 flexible peripheral chains possess liquid crystallinity and solution processability, suitable for use as organic semiconductors. They showed different columnar phases and exhibited higher thermal stability and lower band gaps. The NI derivatives showed larger Stokes shifts, while the PI derivatives exhibited very high molar extinction coefficients. Two solution-processable liquid-crystalline compounds (NI-12 and PI-12) were used to fabricate organic field-effect transistors, with NI-12 derivatives showing a hole mobility of 1.99 cm2/V center dot s and PI-12 derivatives showing a hole mobility of 0.63 cm2/V center dot s at room temperature in normal air conditions.