TY - JOUR
T1 - A dendritic oligoarylamine-substituted benzimidazole derivative as a useful n-type dopant
AU - Uebe, Masashi
AU - Yoshihashi, Yuji
AU - Noda, Kei
AU - Matsubara, Masayuki
AU - Ito, Akihiro
N1 - Funding Information:
This work was supported by the Project of International Standards Development on Energy Conservation of Ministry of Economy, Trade, and Industry of Japan (METI). Numerical calculations were partly performed at the Supercomputer System of Kyoto University (Japan) and the Research Center for Computational Science in Okazaki (Japan). M. U. thanks the JSPS Research Fellowship for Young Scientists.
Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2018
Y1 - 2018
N2 - 4-(N,N-Dimethylamino)phenyl-substituted 1,3-dimethyl-2,3-dihydro-1H-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 of N3-DMBI-H. On the basis of electrochemical, spectroelectrochemical, and quantum chemical calculations, it has been deduced that one-electron-oxidized species for N3-DMBI-H as well as N-DMBI-H are readily converted into diamagnetic cationic species by releasing a hydrogen atom.
AB - 4-(N,N-Dimethylamino)phenyl-substituted 1,3-dimethyl-2,3-dihydro-1H-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 of N3-DMBI-H. On the basis of electrochemical, spectroelectrochemical, and quantum chemical calculations, it has been deduced that one-electron-oxidized species for N3-DMBI-H as well as N-DMBI-H are readily converted into diamagnetic cationic species by releasing a hydrogen atom.
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U2 - 10.1039/c8tc01280f
DO - 10.1039/c8tc01280f
M3 - Article
AN - SCOPUS:85049189504
SN - 2050-7526
VL - 6
SP - 6429
EP - 6439
JO - Journal of Materials Chemistry C
JF - Journal of Materials Chemistry C
IS - 24
ER -