Reference of 914306-50-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 914306-50-6 name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Step 3: Synthesis of (OC-6-21)-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(I II) (abbreviation: [mer-Ir(iPrCzpim)2(iPrpim)]) (0417) Into a 100-mL three-neck flask were put 2.8 g (2.3 mmol) of [Ir(iPrCzpim)2(acac)] (abbreviation) obtained in Step 2, 1 g (3.3 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (abbreviation: HiPrpim), and 20 mL of glycerol, and the mixture was heated and stirred at 150 C. for 12 hours. After reaction for the predetermined time, the reaction solution was filtered and a precipitate was washed with methanol to give a yellow solid. This yellow solid was recrystallized with tetrahydrofuran (THF) to give a yellow solid. The yield was 2.1 g (1.5 mmol) and 64%. Purification by a train sublimation method was performed on 1.0 g of this yellow solid, so that 790 mg (0.52 mmol) of a yellow solid was obtained. The synthesis scheme of Step 3 is shown in (b-3). (0418) Protons (1H) of the yellow solid obtained through Step 3 described above were measured by nuclear magnetic resonance (NMR). The obtained values are shown below. The 1H-NMR chart is shown in FIG. 29. The results revealed that [mer-Ir(iPrCzpim)2(iPrpim)], which is the organometallic complex represented by Structural Formula (600), was obtained in Synthesis Example 2. (0419) 1H-NMR. delta (CD2Cl2): 0.26 (dd, 6H), 0.32 (d, 6H), 1.00 (m, 18H), 1.13 (d, 3H), 1.26 (d, 3H), 2.10 (m, 2H), 2.23 (m, 1H), 2.38 (m, 2H), 2.86 (m, 1H), 6.25 (dd, 2H), 6.32 (d, 1H), 6.48 (d, 1H), 6.56 (m, 2H), 6.63 (dd, 1H), 6.69 (dd, 1H), 6.70 (d, 1H), 6.76 (d, 1H), 6.84 (m, 2H), 6.88 (d, 1H), 7.07 (d, 1H), 7.16 (m, 8H), 7.28 (m, 8H), 7.41 (m, 6H), 7.56 (t, 1), 8.06 (dd, 4H). (0420) Next, an ultraviolet-visible absorption spectrum (absorption spectrum) and an emission spectrum of a dichloromethane solution of [mer-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. 30, 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. 30 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. (0421) As shown in FIG. 30, the organometallic complex [mer-Ir(iPrCzpim)2(iPrpim)] has emission peaks at 481 nm and 515 nm, and blue-green light emission was observed from the dichloromethane solution. (0422) Next, [mer-Ir(iPrCzpim)2(iPrpim)] obtained in this example was analyzed by liquid chromatography-mass spectrometry (LC-MS). (0423) 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. (0424) 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 was prepared by dissolving [mer-Ir(iPrCzpim)2(iPrpim)] in an organic solvent at an arbitrary concentration, and the injection amount was 5.0 muL. (0425) A component with m/z of 1432.64, which is an ion derived from [mer-Ir(iPrCzpim)2(iPrpim)], was subjected to the MS2 analysis by a Targeted-MS2 method. For the Targeted-MS2 analysis, the mass range of a target ion was set to m/z=1432.64±2.0 (isolation window=4) and detection was performed in a positive mode. Measurement was performed with energy (normalized collision energy: NCE) for accelerating a target ion in a collision cell set to 30. The obtained MS spectrum is shown in FIG. 31. (0426) FIG. 31 shows that product ions of [mer-Ir(iPrCzpim)2(iPrpim)] are mainly detected around m/z=1129 and m/z=964. The results in FIG. 31 show characteristics derived from [mer-Ir(iPrCzpim)2(iPrpim)] and therefore can be regarded as important data for identifying [mer-Ir(iPrCzpim)2(iPrpim)] contained in a mixture. (0427) It is presumed that the product ion around m/z=1129 is a cation in a state where the ligand HiPrpim (abbreviation) is …
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, and friends who are interested can also refer to it.
Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; TSUNOI, Toshiaki; INOUE, Hideko; ISHISONE, Takahiro; WATABE, Takeyoshi; (129 pag.)US2017/213989; (2017); A1;,
Imidazole – Wikipedia,
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