Benzimidazole Derivatives: Synthesis, Physical Properties, and n‐Type Semiconducting Properties. Issue 37 (30th July 2014)

• Record Type: Journal Article
• Authors: Mamada, Masashi; Pérez‐Bolívar, César; Kumaki, Daisuke; Esipenko, Nina A.; Tokito, Shizuo; Anzenbacher, Pavel
• Is Part Of: Chemistry. Volume 20:Issue 37(2014)
• Page Start: 11835
• Page End: 11846
• Publication Date: 2014-07-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201403058
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 cm² V⁻¹ s⁻¹.</p> </abstract>