Facile synthesis of arylthiophenyl-functionalized diketopyrrolopyrrole derivatives via direct C–H arylation: characterization and utilization in organic electronic devices. (9th November 2015)

• Record Type: Journal Article
• Authors: Palai, Akshaya Kumar; Kumar, Amit; Sim, Kyoseung; Kwon, Jaehyuk; Shin, Tae Joo; Jang, Soonmin; Cho, Sungwoo; Park, Seung-Un; Pyo, Seungmoon
• Is Part Of: New journal of chemistry. Volume 40:Number 1(2016:Jan.)
• Page Start: 385
• Page End: 392
• Publication Date: 2015-11-09
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c5nj02631h
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : We report the synthesis and characterization of three arylthiophenyl-functionalized diketopyrrolopyrrole derivatives with different end-capping groups via direct C–H arylation. 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.