US EPA

2713117 

Journal Article 

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

Mamada, M; Pérez-Bolívar, C; Kumaki, D; Esipenko, NA; Tokito, S; Anzenbacher, P 

2014 

Yes 

Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 

20 

37 

11835-11846 

English 

25079856 

10.1002/chem.201403058 

WOS:000341630500032 

http://://WOS:000341630500032
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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) . 

Chemistry; Semiconductors; 8650:Electrical & electronics industries