A dendritic oligoarylamine-substituted benzimidazole derivative as a useful n-type dopant. Issue 24 (4th June 2018)

• Record Type: Journal Article
• Authors: Uebe, Masashi; Yoshihashi, Yuji; Noda, Kei; Matsubara, Masayuki; Ito, Akihiro
• Is Part Of: Journal of materials chemistry. Volume 6:Issue 24(2018)
• Page Start: 6429
• Page End: 6439
• Publication Date: 2018-06-04
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c8tc01280f
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : Introduction of a dendritic oligoarylamine group at the 2-position of 1, 3-dimethyl-2, 3-dihydro-1 H -benzimidazole (N3-DMBI-H ) has significantly improved the chemical stability in solution phase. In addition to the preeminent solution-processability ofN3-DMBI-H, the n-type doping ability has also been confirmed with the electrical characteristics of theN3-DMBI-H -doped PCBM thin films. Abstract : 4-( N, N -Dimethylamino)phenyl-substituted 1, 3-dimethyl-2, 3-dihydro-1 H -benzimidazole (N-DMBI-H ) has been reported as a useful solution-processable n-type dopant to control electrical conductivity over a wide range in PCBM ([6, 6]-phenyl-C61 -butyric acid methyl ester) thin films. An approach for increasing the chemical stability of the DMBI-H dopant molecule in solution phase by attachment of dendritic oligoarylamine at the 2-position of the benzimidazole ring (N3-DMBI-H ) has been explored in this study, and moreover the efficacy of the solution-processable n-type dopant has been clarified together with the electronic properties ofN3-DMBI-H . On the basis of electrochemical, spectroelectrochemical, and quantum chemical calculations, it has been deduced that one-electron-oxidized species forN3-DMBI-H as well asN-DMBI-H are readily converted into diamagnetic cationic species by releasing a hydrogen atom.