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 language | English |
|---|---|
| Pages (from-to) | 11835-11846 |
| Number of pages | 12 |
| Journal | Chemistry - A European Journal |
| Volume | 20 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - Jan 1 2014 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Benzimidazole derivatives
T2 - Synthesis, physical properties, and n-type semiconducting properties
AU - Mamada, Masashi
AU - Pérez-Bolívar, César
AU - Kumaki, Daisuke
AU - Esipenko, Nina A.
AU - Tokito, Shizuo
AU - Anzenbacher, Pavel
PY - 2014/1/1
Y1 - 2014/1/1
N2 - 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.
AB - 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.
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U2 - 10.1002/chem.201403058
DO - 10.1002/chem.201403058
M3 - Article
VL - 20
SP - 11835
EP - 11846
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 37
ER -