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

Abstract

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 × 10–5 cm2 V–1 s–1.

Inter‐Ligand Energy Transfer Process in an Ir‐Complex with Expanding π‐Conjugated Ligand

“…The solvent dependency on the emission of bpy‐Im 2 indicates that the observed emission comes from the CT state. Indeed, it is well‐known that the Im moiety is a moderate electron‐donating group (EDG), whereas the bpy moiety is a strong electron‐withdrawing group (EWG). Thus, bpy‐Im 2 can be considered as a donor‐acceptor‐donor (D−A‐D) triad, which shows significant solvatochromism due to the intramolecular charge transfer (ICT) .…”

Polycyclic Aromatic Hydrocarbons Bearing Polyethynyl Bridges: Synthesis, Photophysical Properties, and their Applications

“…Highest activity was shown by compound 95 b which had mobility of 5.2×10 −5 cm 2 / Vs. However, 95 a – c showed very less threshold voltage of about 10 V and very poor I on/off ratio (10–100) [134] . Representative examples of polyalkynylated π‐conjugated PAHs that show mobility greater than 0.1 cm 2 /Vs in OFET applications are provided in Table 2.…”

Phenylethynylanthracene based push–pull molecular systems: tuning the photophysics through para-substituents on the phenyl ring

“…26 Some studies on a few of these molecules have been done with regard to solvent studies and electroluminescence. 9,27–31 Here, a detailed photophysical study has been carried out to understand the effect of para -conjugation on the photophysics of 9-phenylethynylanthracenes. This includes a comparative study on the photophysical, computational, electrochemical and fluorescence polarization properties of these compounds.…”