6626-71-7Relevant academic research and scientific papers
One-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors
Dong, Huanli,Fu, Xiaolong,Hu, Wenping,Li, Yang,Ni, Zhenjie,Siegel, Jay S.,Zhen, Yonggang
, p. 14024 - 14028 (2020)
Aromatic diimides are one of the most important chromophores in the construction of n-type organic semiconductors, which lag far behind their p-type counterpart but are necessary for ambipolar transistors, p-n junctions and organic complementary circuits. Herein, we establish a facile one-pot domino synthetic protocol for aromatic diimides via palladium-catalyzed carbonylation of tetrabromo aromatic precursors. Taking tetrabromocorannulene (TBrCor) and tetrabromo-2,7-di-tert-butylpyrene (TBrPy) as the typical examples, we obtained diimide derivatives in yields of about 50 percent, one order of magnitude higher than that of the traditional multi-step diimidization. As demonstrated in the case of corannulene diimide, the efficient diimidization not only allows the LUMO levels to be lowered significantly but also provides an ordered and closer packing structures, opening up possibilities to the development of n-type semiconducting materials based on a variety of aromatic systems.
Facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-dione by palladium-catalyzed carbonylative amidation
Fuse, Shinichiro,Takahashi, Ryota,Takahashi, Takashi
, p. 3430 - 3434 (2015)
Abstract Described herein is a facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-diones (TPDs) by a palladium-catalyzed carbonylative amidation of commercially available dibromoaryl compounds under mild conditions. TPDs are important st
Functionalized and Degradable Polyphthalaldehyde Derivatives
Lutz, J. Patrick,Davydovich, Oleg,Hannigan, Matthew D.,Moore, Jeffrey S.,Zimmerman, Paul M.,McNeil, Anne J.
supporting information, p. 14544 - 14548 (2019/10/02)
Polymers that depolymerize back to monomers can be repeatedly chemically recycled, thereby reducing their environmental impact. Polyphthalaldehyde is a metastable polymer that can rapidly and quantitatively depolymerize due to its low ceiling temperature. However, the effect of substitution on the physical and chemical properties of polyphthalaldehyde derivatives has not been systematically studied. Herein, we investigate the cationic polymerization of seven o-phthalaldehyde derivatives and demonstrate that judicious choice of substituent results in materials with a wide range of ceiling temperatures (-60 to 106 °C) and decomposition temperatures (109-196 °C). We anticipate that these new polymers and their derivatives will enable researchers to access degradable materials with tunable thermal, physical, and chemical properties.
Pyromellitic dithioimides: Thionation improves air-stability and electron mobility of N-type organic field-effect transistors
Yang, Te-Fang,Huang, Sheng-Han,Chiu, Yi-Pang,Chen, Bo-Hsiang,Shih, Yu-Wei,Chang, Yu-Chang,Yao, Jie-Yi,Lee, Yao-Jen,Kuo, Ming-Yu
supporting information, p. 13772 - 13775 (2015/09/07)
Thionation and fluorination of pyromellitic diimides (PyDIs) increased the electron mobility and on/off ratio of the original diimides by two orders of magnitude and improved the threshold voltage and air-stability of diimide compounds.
Competitive Electron Transfer from the S2 and S1 Excited States of Zinc meso-Tetraphenylporphyrin to a Covalently Bound Pyromellitimide: Dependence on Donor-Acceptor Structure and Solvent
Hayes, Ryan T.,Walsh, Christopher J.,Wasielewski, Michael R.
, p. 2375 - 2381 (2007/10/03)
Zinc meso-tetraphenylporphyrin (ZnTPP) is known to have a relatively slow S2 → S1 internal conversion rate, (1-3 ps) -1, so that electron transfer from S2 to a nearby acceptor is possible. We have synthesized tw
