A class of alkoxy-substituted aromatic condensed ring structural unit and its synthesis method and application
A technology of alkoxy and alkyl, which is applied to a class of alkoxy-substituted aromatic fused ring structural units and their synthesis and application fields, and can solve problems such as complex structures, unfavorable commercial applications of materials, and increased costs
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Embodiment 1
[0088] Embodiment 1, alkoxyl substituted condensed ring conjugated structure (M 1 ) compound (i.e. the specific compound shown in formula I) synthetic
[0089] Its reaction equation is as figure 2 shown. Concrete reaction steps and reaction conditions are as follows:
[0090]
[0091] Under argon protection, n-butyl lithium (50 ml, 2.5M / L, stored in n-hexane) was slowly added to a solution of A (146 g, 50 mmol) in 250 ml of THF at -78 ° C, the The mixture was kept at -78° for 1 hour. Then, pinacol diboronate (25.3 g, 100 mmol) was added, followed by slowly warming to room temperature, and the mixture was stirred overnight. The mixture was extracted twice with ether, washed with distilled water and brine. Further purification by silica gel column chromatography, using hexane as eluent, afforded white solid (15 g, yield 80%), namely 2,5-dimethoxy-1,4-diboronate benzene (B) .
[0092] Add 9.75g (25mmol) of B into a 250mL two-neck flask, under nitrogen protection. Add ...
Embodiment 2
[0095] Embodiment 2, formula M 2 Synthesis of the shown non-fullerene small molecule acceptor (i.e. the specific compound shown in formula I')
[0096] Its reaction equation is as image 3 shown. Concrete reaction steps and reaction conditions are as follows:
[0097]
[0098] Take monomer M 1 (1.98g, 3mmol), after it was dissolved in chloroform (50mL), evacuate the air with argon for 5 minutes, then add 3ml DMF and 5ml phosphorus oxychloride, and react fully at the reflux temperature of chloroform for 16 hours stop after. The reaction solution was cooled to room temperature, slowly added deionized water (30mL), and reacted at room temperature for 2h. After the reaction was completed, it was extracted three times with dichloromethane, and solvents such as dichloromethane were removed by rotary evaporation to obtain the crude product. Further purification was carried out by using petroleum ether / dichloromethane 1:1 (v / v) as the eluent to obtain a yellow solid (1.83 g, y...
Embodiment 3
[0101] Embodiment 3, formula M 3 Synthesis of the shown non-fullerene small molecule acceptor (i.e. the specific compound shown in formula I')
[0102] Its reaction equation is as Figure 4 shown. Concrete reaction steps and reaction conditions are as follows:
[0103]
[0104] Dissolve F (1.07g, 1.5mmol) in chloroform, add H (1.34g 6mmol) and add 1mL pyridine as a catalyst, react at the reflux temperature of chloroform for 12h, add water and extract with dichloromethane after the reaction Three times, solvents such as dichloromethane were removed by rotary evaporation to obtain the crude product, which was further purified by silica gel column chromatography, using petroleum ether / dichloromethane 1:1 as the eluent to obtain a blue-black solid (1.41g, yield 83%) is the target compound M 3 .
[0105] The structural confirmation data is as follows: 1 H NMR (300MHz, CDCl 3 )δ8.93(s,2H),8.63-8.47(m,2H),7.79(dd,J=33.6,8.0Hz,4H),7.56(dd,J=7.3,4.9Hz,2H),4.12(s ,6H),2.56(d,...
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