Synthetic Route of 82777-09-1,Some common heterocyclic compound, 82777-09-1, name is 2′-Iodo-1,1′:3′,1”-terphenyl, molecular formula is C18H13I, 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.
Example 3 Synthesis of Exemplified Compound BOl[0107] [Chem. 14] [0108] The following reagents and solvents were charged into a 100-mL recovery flask. 2 , 8-Dibromodibenzothiophene : 600 mg (1.75 mmol) ( 1 , 3-Bis (diphenylphosphino) propane ) dichloronickel ( II ) : 380 mg (0.70 mmol)Toluene: 24 mLTriethylamine : 1.46 mL After this reaction solution was heated to 90C and was then added with 1.53 mL (10.5 mmol) of 4 , 4 , 5, 5-tetramethyl- 1, 3, 2-dioxaborolane, heating was performed for 6.5 hours. After the reaction solution was cooled to room temperature, the reaction was quenched by addition of water, and an insoluble matter was removed by filtration of the reaction solution. After a reaction product in the filtrate was extracted using toluene, this extracted solution was washed with water and was then dried over sodium sulfate, followed by concentration, so that a crude product was obtained. The obtained crude product was refined by a silica gel column chromatography (eluent: toluene), and 124 mg of intermediate S-Bpin2 was obtained (yield: 16%) . [0109] Then, the following reagents and solvents were charged into a 50-mL recovery flask. 2 ‘ -Iodo-m-terphenyl: 245 mg (0.688 mmol) S-Bpin2:120 mg (0.275 mmol) Tetrakis ( triphenylphosphine ) palladium ( 0 ) : 25 mg (22 umol) Toluene: 6 mLEthanol: 3 mL 30-wt% cesium carbonate aqueous solution: 3 mL This reaction solution was heat-refluxed for 4.5 hours while being stirred in a nitrogen atmosphere. After the reaction was completed, the reaction solution was washed with water and was then dried over sodium sulfate, followed by concentration, so that a crude product was obtained.Next, this crude product was refined by a silica gel column chromatography (eluent: heptane/chloroform=3/l ) , and heating dispersion washing was further performed using a mixed solvent containing hexane and ethanol. After a crystal thus obtained was vacuum dried at 150C, sublimation refining was performed at a pressure of 10~4 Pa and a temperature of 340C, so that 120 mg of a high-purity exemplified compound B01 was obtained (yield: 68%). [0110] The result of identification of the obtainedcompound is shown below. [MALDI-TOF-MS] Observed value:[1H-N R (400 MHz, CDC13) ]delta 7.75-7.42 (m, 6H) , 7.35 (d, 2H) , 7.16-7.01 (m, 22H) , 6.85 (dd, 2H) . In addition, the Tl energy (equivalent wavelength) of the exemplified compound B01 was 423 nm measured by a method similar to that of Example 1. [0111] When the energy gap of the exemplified compound B01 was further measured by a method similar to that of Example 1, the absorption edge of the absorption spectrum was 322 nm, and the energy gap of the exemplified compound B01 was 3.85 eV. [0112] In addition, when the ionization potential of the exemplified compound B01 was measured by a method similar to that of Example 1, 6.49 eV was obtained. [0113] Furthermore, when the LUMO level of the exemplified compound B01 was estimated by a method similar to that of Example 1, it was estimated to be -2.64 eV.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2′-Iodo-1,1′:3’,1”-terphenyl, its application will become more common.
Reference:
Patent; CANON KABUSHIKI KAISHA; KOSUGE, Tetsuya; KAMATANI, Jun; KISHINO, Kengo; TOMONO, Hiroyuki; WO2011/132624; (2011); A1;,
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