According to the analysis of related databases, 914306-50-6, the application of this compound in the production field has become more and more popular.
In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 914306-50-6 as follows. Computed Properties of C21H24N2
Synthesis of (OC-6-22)-bis{5-(9H-carbazol-9-yl)-2-[1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl-kappaN3]phenyl-kappaC}{2-[1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl-kappaN3]phenyl-kappaC}iridium(III) (abbreviation: [fac-Ir(iPrCzpim)2(iPrpim)]) (0430) First, 1.8 g (0.8 mmol) of [Ir(iPrCzpim)2Cl]2 and 150 mL of dichloromethane were put into a 200-mL three-neck flask. A solution obtained by dissolving 0.6 g (2.3 mmol) of silver trifluoromethanesulfonate in 62 mL of methanol in a dark place was put in a dropping funnel attached to the 200-mL three-neck flask in a dark place. This methanol solution of silver trifluoromethanesulfonate was added dropwise into the reaction solution, and stirring was performed at room temperature for 26 hours. After reaction for the predetermined time, the reaction solution was filtered through Celite and the solvent of the resulting filtrate was distilled off to give an ocher solid. Then, all of the obtained ocher solid, 0.94 g (3.1 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (abbreviation: HiPrpim), 15 mL of methanol, and 15 mL of ethanol were put in a 200-mL three-neck flask, and the mixture was refluxed for 36 hours. After reaction for the predetermined time, the solvent of the reaction solution was distilled off to give a yellow solid. A solution obtained by dissolving this yellow solid in tetrahydrofuran (THF) was filtered through a filter aid in which Celite, neutral silica, and Celite were stacked in this order, so that a yellow solution was obtained. The solvent in this yellow solution was distilled off to give a yellow solid. This yellow solid was purified by silica gel column chromatography. Toluene was used as a developing solvent. The solvent of the resulting fraction was distilled off, so that a yellow oily substance was obtained. This yellow oily substance was recrystallized with ethyl acetate and hexane to give a yellow solid. Purification by a train sublimation method was performed on this yellow solid, so that 240 mg (0.17 mmol) of a yellow solid was obtained in a yield of 11%. The synthesis scheme is shown in (c-1). (0431) Protons (1H) of the yellow solid obtained as described above were measured by nuclear magnetic resonance (NMR). The obtained values are shown below. The 1H-NMR chart is shown in FIG. 32. The results revealed that [fac-Ir(iPrCzpim)2(iPrpim)], which is the organometallic complex represented by Structural Formula (600), was obtained in Synthesis Example 2. (0432) 1H-NMR. delta (CD2Cl2): 0.57 (d, 3H), 0.70 (d, 3H), 0.92 (m, 18H), 1.14 (d, 3H), 1.19 (dd, 6H), 1.24 (d, 3H), 2.27 (m, 1H), 2.34 (m, 1H), 2.54 (m, 1H), 2.62 (m, 2H), 2.81 (m, 1H), 6.07 (d, 1H), 6.27 (t, 2H), 6.39 (d, 1H), 6.44 (dd, 1H), 6.52 (t, 1H), 6.67 (dd, 1H), 6.82 (d, 1H), 6.90 (m, 7H), 6.99 (m, 8H), 7.12 (d, 1H), 7.22 (d, 1H), 7.34 (m, 9H), 7.49 (m, 3H), 7.90 (d, 2H), 7.95 (m, 2H). (0433) Next, an ultraviolet-visible absorption spectrum (absorption spectrum) and an emission spectrum of a dichloromethane solution of [fac-Ir(iPrCzpim)2(iPrpim)] were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet and visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used and the dichloromethane solution (0.0100 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was performed at room temperature in such a manner that an absolute PL quantum yield measurement system (C11347-01 manufactured by Hamamatsu Photonics K.K.) was used and the deoxidized dichloromethane solution (0.0100 mmol/L) was sealed in a quartz cell under a nitrogen atmosphere in a glove box (LABstar M13 (1250/780) manufactured by Bright Co., Ltd.). Measurement results of the obtained absorption and emission spectra are shown in FIG. 33, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. Note that the absorption intensity is shown in FIG. 33 using the results obtained in such a way that the absorbance measured by putting only dichloromethane in a quartz cell was subtracted from the absorbance measured by putting the dichloromethane solution (0.0100 mmol/L) in a quartz cell. (0434) As shown in FIG. 33, the organometallic complex [fac-Ir(iPrCzpim)2(iPrpim)] has emission peaks at 479 nm and 514 nm, and blue-green light emission was observed from the dichloromethane solution. (0435) Next, [fac-Ir(iPrCzpim)2(iPrpim)] obtained in this example was analyzed by liquid chromatography-mass spectrometry (LC-MS). (0436) In the analysis by LC-MS, liquid chromatography (LC) separation was carried out with UltiMate 3000 produced by Thermo Fisher Scientific K.K., and the MS analysis was carried out with Q Exactive produced by Thermo Fisher Scientific K.K. (0437) In the LC separation, a given column was used at a column temperature of 40 C., and solution sending was performed in such a manner that an appropriate solvent was selected, the sample w…
According to the analysis of related databases, 914306-50-6, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; TSUNOI, Toshiaki; INOUE, Hideko; ISHISONE, Takahiro; WATABE, Takeyoshi; (129 pag.)US2017/213989; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem