Aza-tetracene analogue of pyrrole monoketone, preparation method and application thereof
A technology of pyrrole monoketone and tetracene, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of complex synthesis steps, low yield and the like, and achieves simple synthesis method, high yield, high yield, etc. The effect of facilitating the transmission of electrons
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Embodiment 1
[0067] A method for preparing an aza-tetracene analogue of pyrrole monoketone, comprising the steps of:
[0068] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 16 h 33 Br (1-bromohexadecane) 4.6 mL, react at room temperature for 4h. The obtained solution was rotary evaporated first, and then purified by a chromatographic column. The ratio of the eluent dichloromethane to petroleum ether was 1:2. Compound II could be obtained by distillation under reduced pressure. The quality of the obtained compound was 1.57 g. The rate is 30%; figure 2 It is the 1H NMR spectrogram of compound II, and the synthesized compound can be proved to be structure II by proton nuclear magnetic resonance spectrum.
[0069] (2) Add 1.00 g of compo...
Embodiment 2
[0072] A method for preparing an aza-tetracene analogue of pyrrole monoketone, comprising the steps of:
[0073] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 7 h 15 Br (bromoisooctane) 2.67 mL, react at room temperature for 4.5h. The obtained solution was distilled under reduced pressure first, and then purified by a chromatographic column. The ratio of the eluent to dichloromethane and petroleum ether was 1:2. Compound II could be obtained by distillation under reduced pressure, and the quality of the obtained compound was 1.60 g. Yield is 40%; Figure 11 It is the 1H NMR spectrogram of compound II, and the synthesized compound can be proved to be structure II by proton nuclear magnetic resonance spectrum.
[0074] (2)...
Embodiment 3
[0077] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 8 h 17 Br 4.6 mL, react at room temperature for 4 h. The obtained solution was rotary-evaporated first, and then purified by a chromatographic column. The ratio of eluent dichloromethane to petroleum ether was 1:2, and compound II could be obtained by distillation under reduced pressure.
[0078] (2) Add 1.00 g of compound (II), 1.05 g of potassium carbonate and 0.63 g of 3-nitro-4-fluorobenzocyanide into a round bottom flask, then add 40 mL of N,N dimethylformamide, and heat at 80 °C, react for 24 h. , and finally the precipitated solid was filtered and then the solvent was distilled off under reduced pressure, and purified by a chromatography column, wherein the volum...
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