73402-91-2Relevant academic research and scientific papers
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.
Synthesis and characterization of diphenyl quinoline and bromine-activated diphenyl quinoline organic phosphors
Pimpalshende,Dhoble
, p. 451 - 455 (2014)
A diphenyl quinoline (DPQ)-conjugated derivative and bromine-activated DPQ (Br-DPQ) were synthesized in an inert gas atmosphere at 140 °C using Friedlander condensation. The compounds showed blue emission under a UV source. The structures were characterized by X-ray diffraction and Fourier transform infrared spectroscopy. The photoluminescence properties of the compounds were analysed using excitation and emission spectra. The synthesized organic phosphors shows bright emission in the blue region, with peaks at 445 and 453 nm, respectively, for DPQ and Br-DPQ in the powder form. The physical and photoluminescence properties of these organic compounds reveal promising blue emitters for high-efficiency organic light-emitting diodes. Copyright
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.
Synthesis of quinolines: Via sequential addition and I2-mediated desulfurative cyclization
Gao, Ziwei,Jian, Yajun,Sun, Huaming,Wang, Yanyan,Yang, Mingming,Zhang, Guofang,Zhang, Weiqiang
supporting information, p. 38889 - 38893 (2021/12/20)
An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed - a two-step Michael additi
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.
Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
, p. 688 - 694 (2020/01/02)
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
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
Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Br?nsted acidic ionic liquid
Gajare, Shivanand,Patil, Audumbar,Hangirgekar, Shankar,Dhanmane, Sushilkumar,Rashinkar, Gajanan
, p. 2417 - 2436 (2020/02/18)
Abstract: Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product. Graphic abstract: [Figure not available: see fulltext.].
MOF-5 as a highly efficient and recyclable catalyst for one pot synthesis of 2,4-disubstituted quinoline derivatives
Di, Jia-Qi,Ma, Cui-Ting,Xiao, Song-Tao,Zhang, Zhan-Hui
, p. 8614 - 8620 (2020/06/09)
A MOF-5-catalyzed three-component coupling reaction was developed as an efficient approach for the synthesis of 2,4-disubstituted quinoline derivatives via a one pot three-component reaction of aromatic amines, aldehydes and alkynes with excellent yields. The easy recovery and reusability of the catalyst, broad substrate scope, short reaction time, high yields of products and solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.
Method for preparing quinoline compounds under catalysis of zirconocene dichloride
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Paragraph 0016-0023; 0048-0053; 0032-0035, (2019/09/14)
The invention discloses a method for preparing quinoline compounds under catalysis of zirconocene dichloride. According to the method, 3-butyne-2-one compounds and an o-aminophenylmercaptan compound are taken as raw materials, zirconium dichloride is take
