- Four new cyclometalated phenylisoquinoline-based Ir(III) complexes: Syntheses, structures, properties and DFT calculations
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Four new cyclometalated phenylisoquinoline-based iridium(III) complexes [Ir(?N)2(bipy)]PF6 (5a-5d) (bipy = 2,2′-bipyridine) have been synthesized and fully characterized, where the ?N ligands are 1-(4-(trifluoromethyl)phenyl)isoquino
- Niu, Zhi-Gang,Liu, Dong,Li, Da-Chao,Zuo, Jing,Yang, Jian-Ming,Su, You-Hui,Yang, Yi-Ding,Li, Gao-Nan
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- Saturated red iridium(iii) complexes containing a unique four-membered Ir-S-C-N backbone: Mild synthesis and application in OLEDs
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A series of new iridium(iii) cyclometalated complexes (4tfmpiq)2Ir(tiptha), (4tfmpiq)2Ir(phdiptha), (4tfmpiq)2Ir(fphdiptha) and (4tfmpiq)2Ir(ipdptha) (4tfmpiq = 4-(4-(trifluoromethyl)phenyl)isoquinoline, tiptha
- Lu, Guangzhao,Yao, Jingwen,Chen, Zhanxiang,Ma, Dongge,Yang, Chuluo
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- Deep-Red and Near-Infrared Iridium Complexes with Fine-Tuned Emission Colors by Adjusting Trifluoromethyl Substitution on Cyclometalated Ligands Combined with Matched Ancillary Ligands for Highly Efficient Phosphorescent Organic Light-Emitting Diodes
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Six novel Ir(C?N)2 (L?X)-type heteroleptic iridium complexes with deep-red and near-infrared region (NIR)-emitting coverage were constructed through the cross matching of various cyclometalating (C?N) and ancillary (LX) ligands. Here, three nov
- Bi, Hai,Chen, Shuonan,Liu, Yu,Tian, Wenjing
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- Phase-selective modulation of TiO2 for visible light-driven C–H arylation: Tuning of absorption and adsorptivity
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To understand and modify TiO2 for organic photoreaction, two points are important: improving light absorption and retaining adsorption sites for organic reagents. Herein, we tuning the absorption and adsorption of TiO2 by introducing
- Bak, Sora,Lee, Sae Mi,Hwang, Hee Min,Lee, Hyoyoung
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- Highly Luminescent Mono- and Dinuclear Cationic Iridium(III) Complexes Containing Phenanthroline-Based Ancillary Ligand
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A new family of mononuclear (1–2) and dinuclear (3–5) cationic iridium(III) complexes have been synthesized and fully characterized. These complexes contain 2-(4-(trifluoromethyl)phenyl)pyridine (cf3ppy, L1) and 1-(4-(trifluoromethyl)phenyl)iso
- Yang, Xiao-Han,Li, Min,Peng, Hui,Zhang, Qian,Wu, Shui-Xing,Xiao, Wan-Qing,Chen, Xing-Liang,Niu, Zhi-Gang,Chen, Guang-Ying,Li, Gao-Nan
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p. 847 - 855
(2019/02/13)
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- Photoluminescence and electroluminescence of four orange-red and red organic iridium(III) complexes
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Using 1-(4-(trifluoromethyl)phenyl)isoquinoline (tfmpiq) and 4-(4-(trifluoromethyl)phenyl) quinazoline (tfmpqz) as the main ligands and pyrazole pyridine derivatives (mepzpy: 2-(3-methyl-1H-pyrazol-5-yl)pyridine, cf3pzpy: 2-(3-(trifluoromethyl)-1H-pyrazol
- Su, Ning,Zheng, You-Xuan
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- Hybrid Catalysis Enabling Room-Temperature Hydrogen Gas Release from N-Heterocycles and Tetrahydronaphthalenes
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Hybrid catalyst systems to achieve acceptorless dehydrogenation of N-heterocycles and tetrahydronaphthalenes-model substrates for liquid organic hydrogen carriers-were developed. A binary hybrid catalysis comprising an acridinium photoredox catalyst and a Pd metal catalyst was effective for the dehydrogenation of N-heterocycles, whereas a ternary hybrid catalysis comprising an acridinium photoredox catalyst, a Pd metal catalyst, and a thiophosphoric imide organocatalyst achieved dehydrogenation of tetrahydronaphthalenes. These hybrid catalyst systems allowed for 2 molar equiv of H2 gas release from six-membered N-heterocycles and tetrahydronaphthalenes under mild conditions, i.e., visible light irradiation at rt. The combined use of two or three different catalyst types was essential for the catalytic activity.
- Kato, Shota,Saga, Yutaka,Kojima, Masahiro,Fuse, Hiromu,Matsunaga, Shigeki,Fukatsu, Arisa,Kondo, Mio,Masaoka, Shigeyuki,Kanai, Motomu
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p. 2204 - 2207
(2017/02/23)
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- Method for solvent accelerated selective dehydrogenation of tetrahydroisoquinoline type compound
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The invention discloses a method for synthesizing 1-substituted-3,4-dihydroisoquinoline through the solvent accelerated selective partial dehydrogenation of a 1-substituted-1,2,3,4-tetrahydroisoquinoline compound. For a simple and easily obtained cyclic amine type compound such as a tetrahydroisoquinoline compound, a corresponding imine compound can be obtained through selective dehydrogenation; the conversion ratio of the cyclic amine type compound is higher; further, the proportion of a partially dehydrogenated product to a fully dehydrogenated product is more than 20 to 1. The method is simple and convenient to operate, is practical, easy and feasible, and is mild in reaction condition; the actual cost is greatly reduced. In addition, a method for synthesizing 3,4-dihydroisoquinoline through the direct dehydrogenation of tetrahydroisoquinoline has the advantages of atom economy and environmental friendliness.
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Paragraph 0039; 0040; 0041; 0042; 0043
(2017/07/22)
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- Synthesis, photophysical, electrochemical and electroluminescence studies of red emitting phosphorescent Ir(III) heteroleptic complexes
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Abstract: Five heteroleptic, cyclometalated (C∧N) Iridium(III) complexes of acetylacetone (acac) and 1-phenyl-isoquinoline (piq) derivatives, Ir(acac)(piq)2, Ir(acac)(2,4-difluoro-piq)2, Ir(acac)(4-trifluoromethyl-piq)2, Ir(acac)(4-N,N-dimethyl-piq)2, Ir(acac)(4-acetyl-piq)2, were synthesized and characterized. The (C ∧N ) 2Ir(acac) complexes in toluene showed phosphorescence (λ max= 598 nm to 658 nm) with quantum yields (0.1 to 0.32) and microsecond lifetimes (0.43 to 1.9 μ s). The complexes were non-luminescent in thin films due to self-quenching but luminescent when lightly doped (5%) in a host organic material, 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl (CBP). The HOMO levels determined using cyclic voltammetric oxidation potentials were in the range ?5.48 to ?5.80 eV. Electroluminescence properties and performance of the Ir complexes doped in CBP (active layer) were studied in a multilayer (ITO/F4TCNQ/TPD/doped CBP/BCP/LiF/Al) organic light emitting device (OLED). The electroluminescense (EL) spectra of the device matched with the phosphorescent spectra of the Ir complexes. The turn-on voltage at ~ 4.5 V, maximum brightness of 7600 cd/m 2 and current efficiency of ~ 7.0 cd/A at a brightness of ~ 100 cd/m 2 indicate that these are promising OLED materials. GRAPHICAL ABSTRACT: Synopsis. Heteroleptic, cyclometalated (C∧N) Iridium(III) complexes of acetylacetone (acac) and 1-phenyl-isoquinoline were synthesized and their photophysical, electrochemical and electroluminescence properties were studied. The OLED of Ir complex as emitting material showed turn-on voltage at ~ 4.5 V, maximum brightness of 7600 cd/m 2 and current efficiency of ~ 7.0 cd/A at a brightness of ~ 100 cd/m 2.[Figure not available: see fulltext.].
- Ali, Farman,Nayak, Pabitra K,Periasamy,Agarwal, Neeraj
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p. 1391 - 1398
(2017/09/25)
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- Photochemical properties of red-emitting tris(cyclometalated) iridium(III) complexes having basic and nitro groups and application to ph sensing and photoinduced cell death
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Cyclometalated iridium(III) complexes, because of their photophysical properties, have the potential for use as luminescent probes for cellular imaging. We previously reported on a pH-activatable iridium complex that contains three N,N-diethylamino groups
- Kando, Aya,Hisamatsu, Yosuke,Ohwada, Hiroki,Itoh, Taiki,Moromizato, Shinsuke,Kohno, Masahiro,Aoki, Shin
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p. 5342 - 5357
(2015/06/16)
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- Enhancing effects of salt formation on catalytic activity and enantioselectivity for asymmetric hydrogenation of isoquinolinium salts by dinuclear halide-bridged iridium complexes bearing chiral diphosphine ligands
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Asymmetric hydrogenation of 1- and 3-substituted and 1,3-disubstituted isoquinolinium chlorides using triply halide-bridged dinuclear iridium complexes [{Ir(H)(diphosphine)} 2(μ -Cl)3]Cl has been achieved by the strategy of HCl salt formation of isoquinolines to afford the corresponding chiral 1,2,3,4-tetrahydroisoquinolines (THIQs) in high yields and with excellent enantioselectivities after simple basic workup. The effects of salt formation have been investigated by time-course experiments, which revealed that the generation of isoquinolinium chlorides clearly prevented formation of the catalytically inactive dinuclear trihydride complex, which was readily generated in the catalytic reduction of salt-free isoquinoline substrates. Based on mechanistic investigations, including by 1H and 31P{1H} NMR studies and the isolation and characterization of several intermediates, the function of the chloride anion of the isoquinolinium chlorides has been elucidated, allowing us to propose a new outer-sphere mechanism involving coordination of the chloride anion of the substrates to an iridium dihydride species along with a hydrogen bond between the chloride ligand and the N-H proton of the substrate salt.
- Kita, Yusuke,Yamaji, Kenta,Higashida, Kosuke,Sathaiah, Kandula,Iimuro, Atuhiro,Mashima, Kazushi
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supporting information
p. 1915 - 1927
(2015/01/30)
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- Total syntheses of menisporphine and daurioxoisoporphine c enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium Salt
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Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.
- Zhang, Jing,Chen, Jie,Zhang, Xiaoyun,Lei, Xiaoguang
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p. 10682 - 10688
(2015/02/19)
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- Synthesis and photophysical studies of iridium complexes of fluorinated phenylisoquinolines
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There have been reported materials emitting green color in both fluorescence and phosphorescence with great success, however efficient red luminescence materials are rare. Recently, it has been reported iridium (III) complexes of 1-(phenyl)isoquinoline (
- Rho, Hyeon Hee,Park, Yong Hwan,Lee, Young Hee,Park, No Gill,Ha, Yunkyoung,Kim, Young Sik
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p. 145 - 155
(2007/10/03)
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- Versatile and Efficient Synthesis of Aryl-1,2,3,4-tetrahydroisoquinolines: Nickel(II) Phosphine Ligand Catalyzed Coupling of Arylmagnesium Halides to Haloisoquinolines
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Dichloronickel(II) (dppp) was used as catalyst to prepare some previously unreported arylisoquinolines 3, which were in turn hydrogenated to aryl-1,2,3,4-tetrahydroisoquinolines 2.This procedure is the most direct and ef
- Pridgen, Lendon N.
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p. 1289 - 1291
(2007/10/02)
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