3297-72-1

Usage

Uses

Used in OLED Industry:
Phenylisoquinoline is used as a ligand for synthesizing OLED dopants, which are essential components in the production of OLEDs. These dopants enhance the performance and efficiency of OLEDs, making them brighter, more energy-efficient, and longer-lasting.
Phenylisoquinoline is used as a chemical intermediate for the synthesis of various organic compounds and pharmaceuticals. Its unique structure and properties make it a valuable building block in the development of new drugs and materials.

InChI:InChI=1/C15H11N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-11H

Upstream product

• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 126798-63-8 Phenyl-(1-phenyl-1H-isoquinolin-2-yl)-methanone 
• 591-51-5 phenyllithium 
• 78133-52-5 dimethyl isoquinolin-1-ylphosphonate 
• 1532-71-4 1-bromoisoquinoline 
• 108-86-1 bromobenzene 
• 981-18-0 triphenyl(phenylazo)methane 
• 1013-88-3 Benzophenone imine 
• 55-21-0 benzamide 
• 19493-44-8 1-chloroisoquinoline 
• 100-58-3 phenylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 119-65-3 isoquinoline 
• 1078-58-6 diphenylzinc 

Downstream Products

• 102548-86-7 1-phenyl-1-p-tolyl-1,2-dihydro-isoquinoline 
• 6637-53-2 3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 380427-47-4 (+)-1-cyano-1-phenyl-1,2-dihydroisoquinoline-2-carboxylic acid vinyl ester 
• 1186193-36-1 Ir(III)(1-phenylisoquinoline^(1-))2(picolinate) 
• 1360607-12-0 1-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]isoquinoline 
• 527686-83-5 platinum(II) (1-phenylisoquinolinato-N,C(2'))(2,4-pentanedionato-O,O) 

Relevant academic research and scientific papers

New synthesis of isoquinoline derivatives by reactions of 2-(2-methoxyethenyl)benzonitriles with organolithiums and lithium dialkylamides

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.

High-efficiency electrophosphorescent fluorene-alt-carbazole copolymers N-grafted with cyclometalated Ir complexes

A series of electrophosphorescent conjugated fluorene-alt-carbazole copolymers are synthesized by Suzuki polycondensation. A diketone-ended alkyl chain which is grafted in the N-position of carbazole serves as a ligand to form a pendant cyclometalated Ir complex with 1-phenylisoquinoline (Piq), 2-naphthylpyridine (Napy), and 2-phenylquinoline (Phq). The PL efficiencies of PFCzIrPiq and PFCzIrPhq copolymers are around 60% and 70%, respectively. EL emission from the backbone of PFCzIrPiq and PFCzIrPhq copolymers is completely quenched even though the Ir complex contents in the polymers are as low as 0.5 mol %. The device of PFCzIrPiq05 copolymer shows the highest external quantum efficiency of 4.9% ph/el and the luminous efficiency of 4.0 cd/A with 240 cd/m2 at a bias voltage of 7.7 V and a peak emission of 610 nm. The device efficiency of PFCzIrPiq05 copolymer still remains high (QE ext = 3.4% ph/el and LE = 2.9 cd/A) with a luminance of 2978 cd/m2 even at a current density of 100 mA/cm2. The enhancement of the device performance could be due to the higher triplet energy and meanwhile to suitable HOMO and LUMO levels for efficient charge injection by introducing a carbazole unit into the polyfluorene backbone at the 3,6-linkage and blending PBD into the copolymers.

A series of red-light-emitting ionic iridium complexes: Structures, excited state properties, and application in electroluminescent devices

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.

Efficient and stable deep-red phosphorescent organic light-emitting diodes based on an iridium complex containing a benzoxazole-substituted ancillary ligand

In the deep red: A biscyclometalated deep-red phosphorescent dopant containing a new ancillary ligand, iridium(III) bis(1-phenylisoquinolinato-N, C2′) (2-(benzo[d]oxazol-2-yl)phenol) (Ir(piq)2bop) has been designed and synthesized. B

Novel cyclometalated Ru(II) complexes containing isoquinoline ligands: Synthesis, characterization, cellular uptake and in vitro cytotoxicity

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

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.

Development of versatile and potent monoquaternary reactivators of acetylcholinesterase

To date, the only treatments developed for poisoning by organophosphorus compounds, the most toxic chemical weapons of mass destruction, have exhibited limited efficacy and versatility. The available causal antidotes are based on reactivation of the enzyme acetylcholinesterase (AChE), which is rapidly and pseudo-irreversibly inhibited by these agents. In this study, we developed a novel series of monoquaternary reactivators combining permanently charged moieties tethered to position 6- of 3-hydroxypyridine-2-aldoxime reactivating subunit. Highlighted representatives (21, 24, and 27; also coded as K1371, K1374, and K1375, respectively) that contained 1-phenylisoquinolinium, 7-amino-1-phenylisoquinolinium and 4-carbamoylpyridinium moieties?as peripheral anionic site ligands, respectively, showed efficacy superior or comparable to that of the clinically used standards. More importantly, these reactivators exhibited wide-spectrum efficacy and were minutely investigated via determination of their reactivation kinetics in parallel with molecular dynamics simulations to study their mechanisms of reactivation of the tabun-inhibited AChE conjugate. To further confirm the potential applicability of these candidates, a mouse in vivo assay was conducted. While K1375 had the lowest acute toxicity and the most suitable pharmacokinetic profile, the oxime K1374 with delayed elimination half-life was the most effective in ameliorating the signs of tabun toxicity. Moreover, both in vitro and in vivo, the versatility of the agents was substantially superior to that of clinically used standards. Their high efficacy and broad-spectrum capability make K1374 and K1375 promising candidates that should be further investigated for their potential as nerve agents and insecticide antidotes.

2-Phosphinoimidazole Ligands: N-H NHC or P-N Coordination Complexes in Palladium-Catalyzed Suzuki-Miyaura Reactions of Aryl Chlorides

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.

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes

The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.

Efficient acceptorless dehydrogenation of hydrogen-rich N-heterocycles photocatalyzed by Ni(OH)2@CdSe/CdS quantum dots

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.