73402-91-2Relevant articles and documents
Phosphine oxide and Amino N-oxide functionalized phenylquinoline-based small molecules: New cathode interfacial layers for high-performance inverted organic solar cells
Chakravarthi, Nallan,Park, Ho-Yeol,Aryal, Um Kanta,Kim, Junyoung,Gal, Yeong-Soon,Song, Myungkwan,Cho, Young-Rae,Jin, Sung-Ho
, p. 111 - 118 (2018)
Two novel small-molecules PO-PhQ and PO-PhQNO, in which both polar phosphine oxide (PO) and N–oxide (NO) groups are incorporated in phenyl quinolone core unit were synthesized as efficient cathode interfacial layers (CILs) for inverted organic solar cells (IOSCs). Because of the phenylquinoline (PhQ) group, both PO-PhQ and PO-PhQNO are endorsed with high electron mobility. Due to the presence of polar P=O and N-oxide groups in their molecular structure, PO-PhQ and PO-PhQNO possess good solubility in polar solvents which make them as suitable candidates for interfacial modification of solution processed multilayer IOSCs. As a result, the power conversion efficiency (PCE) of the inverted devices based polythieno[3,4-b]-thiophene-co-benzodithiophene (PTB7):(6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) active layer with PO-PhQ and PO-PhQNO as CILs achieve PCE values of 9.03 and 8.53%, respectively, with 10–16% improvement than that of the control device with ZnO. In addition, both PO-PhQ and PO-PhQNO make certain the IOSC devices with long-term stability. To the best of our knowledge, this is the first time that cathode interfacial materials based on the combination of PhQ and P=O groups is reported. The effective application of these alcohol solution processed CILs indicate that the lending P=O to PhQ could be very promising strategy in developing high performance and eco-friendly solar cells. Our findings would contribute to enhancing the OSC device performances from synthetically view point of designing new materials.
Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
supporting information, p. 20462 - 20471 (2021/12/03)
The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
Metal-Free Synthesis of 2-Substituted Quinolines via High Chemoselective Domino Condensation/Aza-Prins Cyclization/Retro-Aldol between 2-Alkenylanilines with β-Ketoesters
Nan, Jiang,Chen, Pu,Zhang, Yuxin,Yin, Yun,Wang, Bo,Ma, Yangmin
, p. 14042 - 14054 (2020/11/13)
A highly chemoselective domino condensation/aza-Prins cyclization/retro-aldol between 2-alkenylanilines with β-dicarbonyl compounds under metal-free conditions was accomplished, giving a large category of valuable 2-substituted quinolines in good yields with excellent functional group toleration. This newly established process, adopting β-ketoesters as masked C1 synthons via C-C cleavage, could even be simplified into a three-component [3 + 2 + 1] domino version consisting of exceedingly low-priced commercial starting materials. The synthetic application of products was exemplified by several intriguing chemical operations.
Quinoline compound and synthesis method thereof
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Paragraph 0146-0150, (2020/02/14)
The invention discloses a synthesis method of a quinoline compound. The synthesis method comprises the following steps: adding a diazocarbonyl compound and a 2-vinylaniline compound into a solvent, carrying out a reaction under the protection of an inert
