Synthesis of acenaphthene fused azabenzannulated perylene diimide for ambipolar organic field-effect transistors

Abstract

Azabenzannulated perylene diimides (AzaBPDIs) represent an important class of nitrogen-doped perylene diimides that have attracted considerable attention in the field of organic electronics. However, most AzaBPDIs synthesized via ring-fusion strategies exhibit solely n-type transport characteristics and lack efficient, balanced ambipolar transport capabilities. This limitation restricts their applications in complementary circuits and multifunctional optoelectronic devices. To address this challenge, this study introduces an acenaphthene unit to structurally modify AzaBPDI molecules through a ring-fusion strategy, yielding a new derivative termed acenaphthene-fused azabenzannulated perylene diimide (AABPDI). Systematic studies demonstrate that AABPDI exhibit favorable ambipolar transport behavior in organic field-effect transistors, with an electron mobility of up to 0.165 cm2 V-1 s-1 and a hole mobility of 0.011 cm2 V-1 s-1. This work confirms the potential of the acenaphthene-fused strategy in developing high-performance ambipolar AzaBPDI semiconductors, providing a reference for the subsequent design of related materials and device applications.