Benzimidazole derivatives: Synthesis, physical properties, and n-type semiconducting properties

Masashi Mamada, César Pérez-Bolívar, Daisuke Kumaki, Nina A. Esipenko, Shizuo Tokito, Pavel Anzenbacher

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)


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 ∼10-2cm2V-1s-1.

Original languageEnglish
Pages (from-to)11835-11846
Number of pages12
JournalChemistry - A European Journal
Issue number37
Publication statusPublished - Sept 8 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Catalysis
  • Organic Chemistry


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