A dendritic oligoarylamine-substituted benzimidazole derivative as a useful n-type dopant

Masashi Uebe, Yuji Yoshihashi, Kei Noda, Masayuki Matsubara, Akihiro Ito

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish
Pages (from-to)6429-6439
Number of pages11
JournalJournal of Materials Chemistry C
Volume6
Issue number24
DOIs
Publication statusPublished - 2018 Jan 1

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Doping (additives)
Derivatives
Butyric acid
Chemical stability
Electronic properties
Hydrogen
Esters
Thin films
Atoms
Molecules
Electrons
benzimidazole
Electric Conductivity
(6,6)-phenyl C61-butyric acid methyl ester

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

A dendritic oligoarylamine-substituted benzimidazole derivative as a useful n-type dopant. / Uebe, Masashi; Yoshihashi, Yuji; Noda, Kei; Matsubara, Masayuki; Ito, Akihiro.

In: Journal of Materials Chemistry C, Vol. 6, No. 24, 01.01.2018, p. 6429-6439.

Research output: Contribution to journalArticle

Uebe, Masashi ; Yoshihashi, Yuji ; Noda, Kei ; Matsubara, Masayuki ; Ito, Akihiro. / A dendritic oligoarylamine-substituted benzimidazole derivative as a useful n-type dopant. In: Journal of Materials Chemistry C. 2018 ; Vol. 6, No. 24. pp. 6429-6439.
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