Synthesis, Photophysical Properties, and Field-Effect Characteristics of (Ethynylphenyl)benzimidazole-Decorated Anthracene and Perylene Bisimide Derivatives

A series of anthracene and perylene bisimide derivatives with electron-withdrawing benzimidazole substituents has been designed and prepared. Detailed studies on the electrochemical and photophysical properties as well as the field-effect mobilities of these new compounds were explored. The incorporation of electron-withdrawing benzimidazole groups lowered the LUMO levels in both anthracene and perylene bisimide derivatives compared to those of the parent compounds. Strong emission was observed for all anthracene derivatives, but only weak emission was observed for perylene bisimide derivatives. The anthracene derivatives showed typical p-type semiconducting character, even when the derivatives were substituted with electron-withdrawing benzimidazole groups at the 9- and 10-positions, which apparently does not lower the LUMO levels to transform them into electron-transporting molecules. Perylene bisimide derivatives displayed typical n-channel semiconducting properties with low threshold voltages and electron mobilities of ca. 5.2?X?105 cm2?V1?s1.