title: Benzimidazole derivatives: synthesis, physical properties, and n-type semiconducting properties.
abstract: A series of new benzimidazole derivatives were synthesized by the solid-state condensation and direct sublimation (SSC-DS) method and their physical properties were investigated. The reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. On the other hand, the substituents of the benzimidazole ring allowed fine tuning of the emission maxima, fluorescence quantum yields, and redox potentials. The HOMO-LUMO levels were estimated by cyclic voltammetry in film on indium tin oxide (ITO) and compared with values obtained by other methods. The described benzimidazoles showed high crystallinity, which is attributed to a high planarity and interactions between carbon and heteroatoms. These compounds showed n-type semiconducting behavior in organic field-effect transistors (OFETs). Optimized devices for fluorinated NTCBI (naphthalene tetracarboxylic bisbenzimidazole) showed respectable electron mobilities of ∼10(-2)  cm(2)  V(-1)  s(-1) .
authors: Department of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Bowling Green, Ohio 43403 (USA), Fax: (+1) 419-372-9809; Research Center for Organic Electronics, Graduate School of Science and Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510 (Japan), Fax: (+81) 238-26-3788.
authors: Masashi
authors: M
authors: Mamada
authors: César
authors: C
authors: Pérez-Bolívar
authors: Daisuke
authors: D
authors: Kumaki
authors: Nina A
authors: NA
authors: Esipenko
authors: Shizuo
authors: S
authors: Tokito
authors: Pavel
authors: P
authors: Anzenbacher
keywords: dyes/pigments; green chemistry; heterocycles; organic field-effect transistors; semiconductors