5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices

Motonori Watanabe, Naoki Uemura, Shintaro Ida, Hidehisa Hagiwara, Kenta Goto, Tatsumi Ishihara

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. Propyl and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied molecular orbital, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO2/FTO substrate, oxidative photocurrents were observed.

Original languageEnglish
Pages (from-to)4280-4287
Number of pages8
JournalTetrahedron
Volume72
Issue number29
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Indigo Carmine
Molecular orbitals
Optoelectronic devices
Density functional theory
Equipment and Supplies
Chloroform
Photocurrents
X-Ray Diffraction
Solubility
Cyclic voltammetry
Mass spectrometry
Absorption spectra
Mass Spectrometry
Crystal structure
Nuclear magnetic resonance
X ray diffraction
Molecules
Substrates

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices. / Watanabe, Motonori; Uemura, Naoki; Ida, Shintaro; Hagiwara, Hidehisa; Goto, Kenta; Ishihara, Tatsumi.

In: Tetrahedron, Vol. 72, No. 29, 01.01.2016, p. 4280-4287.

Research output: Contribution to journalArticle

Watanabe, Motonori ; Uemura, Naoki ; Ida, Shintaro ; Hagiwara, Hidehisa ; Goto, Kenta ; Ishihara, Tatsumi. / 5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices. In: Tetrahedron. 2016 ; Vol. 72, No. 29. pp. 4280-4287.
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