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5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices
- Source :
- Tetrahedron. 72:4280-4287
- Publication Year :
- 2016
- Publisher :
- Elsevier BV, 2016.
-
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.
- Subjects :
- chemistry.chemical_classification
Absorption spectroscopy
Chemistry
Organic Chemistry
Stacking
02 engineering and technology
Crystal structure
010402 general chemistry
021001 nanoscience & nanotechnology
01 natural sciences
Biochemistry
Indigo
0104 chemical sciences
Drug Discovery
Physical chemistry
Organic chemistry
Density functional theory
Cyclic voltammetry
0210 nano-technology
HOMO/LUMO
Alkyl
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 72
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........11090ce9013ebd5f8abcf50aa2065932