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Relevant academic research and scientific papers

Tunable Emission Color of Iridium(III) Complexes with Phenylpyrazole Derivatives as the Main Ligands for Organic Light-Emitting Diodes

Seven cyclometalated iridium(III) complexes Ir1-Ir7 based on phenylpyrazole derivatives as main ligands and tetraphenylimidodiphosphinate (tpip) as the ancillary ligand were synthesized and fully characterized. The proligands of 1-[4-(trifluoromethyl)phenyl]-1H-pyrazole (cf3ppz, 2a), substituted phenyl-2H-indazole {2-phenyl-2H-indazole (h-1-pidz, 2b), 2-(4-fluorophenyl)-2H-indazole (f-1-pidz, 2c), and 2-[4-(trifluoromethyl)phenyl]-2H-indazole (cf3-1-pidz, 2d)}, and substituted phenyl-1H-indazole {1-phenyl-1H-indazole (h-7-pidz, 2e), 1-(4-fluorophenyl)-1H-indazole (f-7-pidz, 2f), and 1-[4-(trifluoromethyl)phenyl]-1H-indazole (cf3-7-pidz, 2g)} were prepared with good yields. The emission maxima of all Ir(III) complexes can be tuned from 453 to 576 nm with different photoluminescence quantum yields (10.4-70.9%) by varying the type of substituent on the different main ligand frameworks. The organic light-emitting diodes using Ir(III) complexes as the emitters with blue, bluish-green, and yellow colors exhibit a maximum current efficiency and an external quantum efficiency of 39.2 cd A-1 and 14.8%, respectively.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

Manganese-Catalyzed Electrochemical Tandem Azidation-Coarctate Reaction: Easy Access to 2-Azo-benzonitriles

A one-pot cascade transformation consisting of an electrochemically driven azidation of 2H-indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.

Efficient synthesis of 2-aryl-2: H -indazoles by base-catalyzed benzyl C-H deprotonation and cyclization

A straightforward and efficient method for the preparation of 2-aryl-2H-indazoles from ortho-alkyl substituted azoxybenzenes is presented. The reaction proceeds through base-catalyzed benzyl C-H deprotonation and cyclization to afford 2-aryl-2H-indazoles

Synthesis method of 2H-indazole and derivatives thereof

The invention discloses a synthetic reaction of 2H-indazole and derivatives thereof under a metal-free condition. The new strategy has the advantages of no metal participation, wide substrate range and good functional group compatibility, and an efficient

New yellow-emitting iridium(III) complexes containing 2-phenyl-2H-indazole-based ligands for high efficient OLEDs with EQE over 25%

Six new pidz-based bis-cyclometalated Ir(III) complexes (Ir1-Ir6) have been synthesized and characterized. These complexes contain 2-phenyl-2H-indazole (pidz, 2a), 2-(4-fluorophenyl)–2H-indazole (fpidz, 2b), 2-(p-tolyl)–2H-indazole (ch3pidz, 2c), 2-(4-(trifluoromethyl)phenyl)–2H-indazole (cf3pidz, 2d), 2-(2,4-difluorophenyl)–2H-indazole (2,4-f2pidz, 2e) and 2-(3,5-difluorophenyl)–2H-indazole (3,5-f2pidz, 2f) as cyclometalated (C∧N) ligands, and acetylacetone (acacH) as ancillary ligand. The crystal structure of Ir2 has been determined by X-ray analysis. Different substituents of C∧N ligand in Ir2-Ir6 induce either a bathochromic or hypsochromic shift in the absorption spectra relative to the parent complex Ir1. The phenomenon is further well explained by DFT calculation and electrochemical study. All of the iridium(III) complexes are yellow emissive with quantum yields of 13.1–32.3% and lifetimes of 1.32–1.77 μs in solution at room temperature. We demonstrate that their emission originates from a hybrid 3MLCT/3ILCT/3LLCT excited state on the basis of the experimental and theoretical investigation. The corresponding yellow-emitting devices based on complexes Ir1, Ir2 and Ir4 can produce efficient electrophosphorescence with a luminance efficiency of 35.1–52.2 cd·A-1, a power efficiency of 20.8–32.1 lm·W?1 and an external quantum efficiency of up to 25.6%. All these EL data definitely suggest the bulky –CF3 skeleton in the doped materials could benefit the fabrication of high-efficiency phosphorescent OLEDs.

Preparation method 2 - substituted - 222H-indazole compound

The invention provides a preparation method of a 2-substituent-2H-indazole compound. With a cuprous catalyst, a coupling reaction is carried out to substituted 1H-indazole and aryliodonium salt in a low-molecular polar organic solvent to obtain a corresponding 2-substituent-2H-indazole compound, wherein the molar ratio of the 1H-indazole to the aryliodonium salt is 1:1.2. According to the method,the reaction route starts from the 1H-indazole compound which is easy to obtain; with the low-cost cuprous compound as a catalyst, the reaction condition is gentle and yield of produced target compound is high. The method also has good compatibility with various functional groups and can be widely applied to synthesize 2-substituent-2H-indazole compounds having different substituent groups. The method has important application value.

Synthesis of (2H)-Indazoles from Azobenzenes Using Paraformaldehyde as a One-Carbon Synthon

Rhodium(III)-catalyzed hydroxymethylation followed by intramolecular annulation of azobenzenes using paraformaldehyde as a valuable C1-feedstock is described. The method is readily extended to the coupling reaction between azobenzenes and trifluoroacetaldehyde. This transformation efficiently produces a range of C3-unsubstituted and C3-trifluoromethylated (2H)-indazoles, which are important targets in the development of novel bioactive compounds. Excellent chemoselectivity and functional group tolerance were observed. The synthetic transformation of C3-unsubstituted (2H)-indazoles highlights the utility of the developed method. (Figure presented.).

Direct Acyl Radical Addition to 2 H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids

A direct acyl radical addition to 2H-indazoles has been achieved for the first time, where the less-aromatic quinonoid 2H-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2H-indazoles, the current method utilizes the radical acceptability of 2H-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-acyl-2H-indazoles with three points of structural diversification in 25%-83% yields.