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Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C-H arylation: characterization and utilization in organic electronic devices
- Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C-H arylation: characterization and utilization in organic electronic devices
- 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
- New Journal of Chemistry, 40(1), 385-392
- Article Type
- Absorption Spectroscopy; Aromatic Compound; Arylation; Arylthiophenyl; Atomic Force Microscopy; Catalyst; Chemical Bond; Chemical Structure; Cyclic Potentiometry; Density Functional Theory; Electron; Field Effect Transistor; Film; Optics; Palladium; Priority Journal; Pyrrole Derivative; Synthesis; Thermogravimetry; Thermostability; Ultraviolet Spectroscopy; Unclassified Drug; X Ray Diffraction
- 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.
- Royal Society of Chemistry
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