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Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C-H arylation: characterization and utilization in organic electronic devices

Title
Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C-H arylation: characterization and utilization in organic electronic devices
Authors
Palai, AK[Palai, Akshaya Kumar]Kumar, A[Kumar, Amit]Sim, K[Sim, Kyoseung]Kwon, J[Kwon, Jaehyuk]Shin, TJ[Shin, Tae Joo]Jang, S[Jang, Soonmin]Cho, S[Cho, Sungwoo]Park, SU[Park, Seung-Un]Pyo, S[Pyo, Seungmoon]
DGIST Authors
Cho, S[Cho, Sungwoo]
Issue Date
2016
Citation
New Journal of Chemistry, 40(1), 385-392
Type
Article
Article Type
Article
Keywords
Absorption SpectroscopyAromatic CompoundArylationArylthiophenylAtomic Force MicroscopyCatalystChemical BondChemical StructureCyclic PotentiometryDensity Functional TheoryElectronField Effect TransistorFilmOpticsPalladiumPriority JournalPyrrole DerivativeSynthesisThermogravimetryThermostabilityUltraviolet SpectroscopyUnclassified DrugX Ray Diffraction
ISSN
1144-0546
Abstract
A series of symmetrically arylthiophenyl-functionalized diketopyrrolopyrrole (DPP) derivatives were synthesized via palladium-catalyzed direct C-H arylation to develop an active material for organic electronic devices. The properties of DPPs could be tuned by simple variation of the end groups such as t-butylphenyl, cyanophenyl and methoxynaphthyl. The effect of the substituent on the optical, electrochemical, and thermal properties of DPPs was evaluated using UV-visible spectroscopy, cyclic voltammetry, and thermogravimetric analysis. The morphology and molecular packing of thin-films of DPPs were analyzed by atomic force microscopy (AFM), density functional theory (DFT) calculations, and two-dimensional grazing incidence X-ray diffraction (2D-GIXD) experiments. Utilization of the synthesized DPPs as channel materials in organic field-effect transistors was demonstrated. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016.
URI
http://hdl.handle.net/20.500.11750/2794
DOI
10.1039/c5nj02631h
Publisher
Royal Society of Chemistry
Files:
There are no files associated with this item.
Collection:
Center for Core Research Facilities1. Journal Articles


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