3297-72-1Relevant articles and documents
New synthesis of isoquinoline derivatives by reactions of 2-(2-methoxyethenyl)benzonitriles with organolithiums and lithium dialkylamides
Kobayashi, Kazuhiro,Shiokawa, Taiyo,Morikawa, Osamu,Konishi, Hisatoshi
, p. 236 - 237 (2004)
A simple and efficient synthesis of 1-alkyl(or aryl)isoquinoline and isoquinolin-1-amine derivatives based on intramolecular cyclization of 2-(2-methoxyethenyl)benzonitriles initiated by the addition of alkyl(or aryl)lithiums and lithium dialkylamides to the nitrile carbons, respectively, is described.
A series of red-light-emitting ionic iridium complexes: Structures, excited state properties, and application in electroluminescent devices
Liu, Shu-Juan,Zhao, Qiang,Fan, Qu-Li,Huang, Wei
, p. 2177 - 2185 (2008)
A series of ionic diiminoiridium complexes [Ir(piq-C∧N) 2(L-N∧N)](PF6) were prepared, where piq-C∧N is 1-phenylisoquinolinato and L-N∧N are bidentate N-coordinating ligands: 2,2′-bipyridine (bpy), 4,4′-dimethyl-2,2′-bipyridine (mbpym), 5,5′-bis(thiopen-2-yl)-2,2′-bipyridine (tbpyt), and 5,5′-bis(9,9-dioctylfluoren-2-yl)-2,2′-bipyridine (FbpyF). X-ray diffraction studies of [Ir(piq)2(mbpym)](PF6) revealed that the iridium center adopts a distorted octahedral geometry. All complexes exhibited intense and long-lived emission at room temperature. The substituents on the 2,2′-bipyridine moieties influence the photophysical and electrochemical properties. The excited states were investigated through theoretical calculations together with photophysical and electrochemical properties. It was found that the excited state of the [Ir(piq) 2(FbpyF)](PF6) complex can be assigned to a mixed character of 3LC (πN∧N→π *N∧N), 3MLCT, 3LLCT (π C∧N→π*N∧N), and 3LC (πC∧N→π*C∧N). In addition, the alkylfluorene-substituted complex, [Ir(piq)2(FbpyF)](PF6), had relatively high quantum efficiency and good film-forming ability, and it was expected to be a good candidate for lighting and display applications. A nondoped, single-layer device that incorporates this complex as a light-emitting layer was fabricated and red phosphorescence was obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Novel cyclometalated Ru(II) complexes containing isoquinoline ligands: Synthesis, characterization, cellular uptake and in vitro cytotoxicity
Chen, Jincan,Wang, Jie,Deng, Yuanyuan,Li, Baojun,Li, Chengpeng,Lin, Yuxue,Yang, Dongbin,Zhang, Huanyun,Chen, Lanmei,Wang, Tao
, (2020)
Two novel cyclometalated Ru(II) complexes containing isoquinoline ligand, [Ru(bpy)2(1-Ph-IQ)](PF6), (bpy = 2,2′-bipyridine; 1-Ph-IQ = 1-phenylisoquinoline; RuIQ-1) and [Ru(phen)2(1-Ph-IQ)](PF6) (phen = 1,10-phenanthroline; RuIQ-2) were found to show high cytotoxic activity against NCI–H460, A549, HeLa and MCF-7 cell lines. Notably, both of them exhibited IC50 values that were an order of magnitude lower than those of clinical cisplatin and two structurally similar Ru(II)-isoquinoline complexes [Ru(bpy)2(1-Py-IQ)](PF6)2 (Ru3) and [Ru(phen)2(1-Py-IQ)](PF6)2 (Ru4) (1-Py-IQ = 1-pyridine-2-yl). The cellular uptake and intracellular localization displayed that the two cyclometalated Ru(II) complexes entered NCI–H460 cancer cells dominantly via endocytosis pathway, and preferentially distributed in the nucleus. Further investigations on the apoptosis-inducing mechanisms of RuIQ-1 and RuIQ-2 revealed that the two complexes could cause S, G2/M double-cycle arrest by regulating cell cycle related proteins. The two complexes also could reduce the mitochondrial membrane potential (MMP), promote the generation of intracellular ROS and trigger DNA damage, and then lead to apoptosis-mediated cell death. More importantly, RuIQ-2 exhibits low toxicity both towards normal HBE cells in vitro and zebrafish embryos in vivo. Accordingly, the developed complexes hold great potential to be developed as novel therapeutics for effective and low-toxic cancer treatment.
Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles
Burton, Paul M.,Cooper, Alasdair K.,Donohoe, William,Greaves, Megan E.,Kennedy, Alan R.,Nelson, David J.,Ronson, Thomas O.
, p. 14074 - 14082 (2021/11/12)
A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.
2-Phosphinoimidazole Ligands: N-H NHC or P-N Coordination Complexes in Palladium-Catalyzed Suzuki-Miyaura Reactions of Aryl Chlorides
Martinez, Erin E.,Larson, Alexandra J. S.,Fuller, Sydney K.,Petersen, Kathryn M.,Smith, Stacey J.,Michaelis, David J.
supporting information, p. 1560 - 1564 (2021/05/29)
We report the synthesis of two palladium 2-(dialkylphosphino)imidazole complexes and demonstrate their activity as catalysts for Suzuki-Miyaura reactions with (hetero)aryl chlorides at room temperature. Our mechanistic studies demonstrate that these palladium complexes exist as an equilibrium mixture between the P-N coordinated and N-H NHC forms of ligand. Our studies suggest that the N-H NHC form may be important for high catalytic activity in Suzuki-Miyaura reactions with aryl chlorides. These reactions proceed at or near room temperature in good to excellent yields. Heteroaryl chlorides are also reactive at lower catalyst loadings.
Efficient acceptorless dehydrogenation of hydrogen-rich N-heterocycles photocatalyzed by Ni(OH)2@CdSe/CdS quantum dots
Liu, Yanpeng,Yu, Tianjun,Zeng, Yi,Chen, Jinping,Yang, Guoqiang,Li, Yi
, p. 3810 - 3817 (2021/06/18)
Hydrogen storage using liquid organic hydrogen carriers (LOHCs) is a promising hydrogen storage technology; however, the hydrogen release process typically requires a high temperature. Developing dehydrogenation technology under mild conditions is highly desirable. Herein, a new approach for photocatalytic acceptorless dehydrogenation of hydrogen-rich LOHCs using Ni(OH)2@CdSe/CdS QDs as the photocatalyst was demonstrated. 1,2,3,4-Tetrahydroquinoline (THQ), iso-THQ, indoline, and their derivatives were selected as hydrogen-rich substrates, which exhibit excellent dehydrogenation efficiency with the release of hydrogen photocatalyzed by Ni(OH)2@CdSe/CdS QDs. Up to 100% yields of hydrogen and over 90% yields of complete dehydrogenation products were obtained at ambient temperature. Isotope tracer studies indicate a stepwise pathway, beginning with the photocatalytic oxidation of the substrate to release a proton and followed by proton exchange with heavy water. This work provides a promising alternative strategy to develop highly efficient, low cost and earth-abundant photocatalysts for acceptorless dehydrogenation of hydrogen-rich LOHCs.
