Electric Literature of 2622-63-1,Some common heterocyclic compound, 2622-63-1, name is 1-Methyl-2-phenyl-1H-benzo[d]imidazole, molecular formula is C14H12N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The synthesis of (L)2Ir(acac) is outlined in Scheme 13. To 2-ethoxyethanol (10 mL) was added 1 mmol of one of the compounds obtained in Examples 1, 2, or 4-9, and then added 1 mmol of iridium trichloride hydrate and water (3 mL). The reaction mixture was then stirred under nitrogen gas at 80° C. for 12 h. The mixture was cooled to room temperature and filtered. The collected solid was washed with ethanol and n-hexane several times, and dried under vacuum to produce cyclometalated Ir(II)-mu-chloro-bridged dimer. The iridium chloro-bridged dimer, acetylacetone (5 mmol), and Na2CO3 (10 mmol) was dissolved in 2-ethoxyethanol (15 mL) and the reaction mixture stirred under nitrogen at 80° C. for 6 h. The mixture was cooled to room temperature and filtered. The collected solid was sequentially washed with water, ethanol, and ether, and purified by vacuum sublimation to give the title compound. Example 14 Synthesis of Ir(Mpb)2(acac) (II-1) Mpb obtained in Example 1 was used as the ligand (L) to produce the title complex II-1 in a yield of 76percent according to the detailed steps described in Example 13. The X-ray structure of complex II-1 is shown in FIG. 2. The UV absorption spectrum and the phosphorescence emission spectrum of complex II-1 in dichloromethane are shown in FIG. 3. The complex II-1 emits a green light having a peak wavelength of 510 nm. 1H NMR (CDCl3, delta): 1.76 (s, 6 H), 4.25 (s, 6 H), 5.15 (s, 1 H), 6.38 (d, J=7.6 Hz, 2 H), 6.57 (t, J=8.0 Hz, 2 H), 6.78 (t, J=7.6 Hz, 2 H), 7.26 (t, J=8.4 Hz, 2 H), 7.37 (t, J=7.2 Hz, 2 H), 7.44 (d, J=8.4 Hz, 2 H), 7.65 (d, J=8.0 Hz, 2 H), 7.75 (d, J=8.4 Hz, 2 H). HRMS (EI): calculated for C33H29IrO2N4 (M+) 706.1920, measured 706.1926.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-2-phenyl-1H-benzo[d]imidazole, its application will become more common.