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 journalArticle

20 Citations (Scopus)

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 ∼10-2cm2V-1s-1.

Original languageEnglish
Pages (from-to)11835-11846
Number of pages12
JournalChemistry - A European Journal
Volume20
Issue number37
DOIs
Publication statusPublished - Jan 1 2014
Externally publishedYes

Fingerprint

Organic field effect transistors
Electron mobility
Sublimation
Quantum yield
Naphthalene
Tin oxides
Indium
Cyclic voltammetry
Condensation
Tuning
Physical properties
Fluorescence
Benzimidazoles
Derivatives
Carbon
Diamines
Anhydrides
Oxidation-Reduction
benzimidazole
bis-benzimidazole

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Benzimidazole derivatives : Synthesis, physical properties, and n-type semiconducting properties. / Mamada, Masashi; Pérez-Bolívar, César; Kumaki, Daisuke; Esipenko, Nina A.; Tokito, Shizuo; Anzenbacher, Pavel.

In: Chemistry - A European Journal, Vol. 20, No. 37, 01.01.2014, p. 11835-11846.

Research output: Contribution to journalArticle

Mamada, M, Pérez-Bolívar, C, Kumaki, D, Esipenko, NA, Tokito, S & Anzenbacher, P 2014, 'Benzimidazole derivatives: Synthesis, physical properties, and n-type semiconducting properties', Chemistry - A European Journal, vol. 20, no. 37, pp. 11835-11846. https://doi.org/10.1002/chem.201403058
Mamada, Masashi ; Pérez-Bolívar, César ; Kumaki, Daisuke ; Esipenko, Nina A. ; Tokito, Shizuo ; Anzenbacher, Pavel. / Benzimidazole derivatives : Synthesis, physical properties, and n-type semiconducting properties. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 37. pp. 11835-11846.
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