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A kind of azepine-2,7-dione acceptor unit and its application

A receptor unit, azepine technology, applied in the field of azepine-2,7-dione receptor unit, which can solve the problems of exhaustion of fossil fuels and the impact of fossil fuels on global climate and environment.

Active Publication Date: 2018-08-07
合肥市激子能源技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the one hand, fossil fuels will eventually be exhausted, and new energy alternatives are urgently needed; on the other hand, the excessive use of fossil fuels seriously affects the global climate and environment

Method used

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  • A kind of azepine-2,7-dione acceptor unit and its application
  • A kind of azepine-2,7-dione acceptor unit and its application
  • A kind of azepine-2,7-dione acceptor unit and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: attributed to the preparation of the acceptor unit TTA-Br of general formula (I) structure

[0086]

[0087] The starting material thieno[3,2-b]thiophene-3-carboxylate ethyl ester (1), the preparation of TMPMgCl LiCl can refer to the literature synthesis (Selective Multiple Magnesiations of the Thieno[3,2-b]thiophene Scaffold.P. Knochel et al, Chem. Eur. J., 2011, 17, 866-872.).

[0088] (a) Synthesis of ethyl 2-tributyltinthieno[3,2-b]thiophene-3-carboxylate (2)

[0089] 1.06g of compound (1) was dissolved in 20mL of dry tetrahydrofuran, and 6.8mL of 1.1M TMPMgCl LiCl was added dropwise thereto under a nitrogen atmosphere at -20°C. After the addition was complete, it was stirred at -20°C for 2 hours, and then Add 2.2mL tributyltin chloride, raise the temperature to room temperature and react for 8-12 hours. After the reaction is completed, pour the reaction liquid into water to quench, and extract twice with petroleum ether; combine the obtained organ...

Embodiment 2

[0115] Embodiment 2: the preparation of acceptor unit BTPA-Br attributed to general formula (II) structure

[0116]

[0117] (a) Synthesis of 2-tributyltinthiophene-3-methyl carboxylate (2)

[0118] 1.42g of compound (1) was dissolved in 40mL of dry tetrahydrofuran, and 13.6mL of 1.1M TMPMgCl LiCl was added dropwise thereto under a nitrogen atmosphere at -20°C. After the addition was complete, it was stirred at -20°C for 2 hours, and then Add 4.4mL tributyltin chloride, raise the temperature to room temperature and react for 8-12 hours. After the reaction is completed, pour the reaction liquid into water to quench, extract twice with petroleum ether, combine the organic phases, dry, filter, and spin dry to obtain crude product, the resulting crude product was passed through Al 2 o 3 Neutral column purification yielded 2.76 g of compound 2 (64%).

[0119] 1 H NMR (CDCl 3 ,400MHz,δ / ppm):7.69(m,1H),7.55(m,1H),3.86(s,3H),1.55(m,6H),1.32(m,6H),1.17(m,6H), 0.89(t,J=7.3Hz,9H...

Embodiment 3

[0137] Copolymerize with TTA-Br prepared in Example 1 and 4,4'-bis(tetradecyl)-5,5'-bis(trimethyltin-yl)-2,2'-bithiophene as monomers Obtain copolymer PTTABT, reaction process is as follows:

[0138]

[0139] Dissolve 78.6 mg of TTA-Br and 88.5 mg of 4,4'-bis(tetradecyl)-5,5'-bis(trimethyltinyl)-2,2'-bithiophene in 20 mL of freshly distilled toluene , add 7mg Pd(PPh 3 ) 4 , and then pass argon for 15 minutes; then under the protection of argon, the solution was heated to reflux for 120 hours, and after the reaction was completed, it was cooled to room temperature, and the reaction solution was dropped into 150mL of methanol, and the crude product was obtained by suction filtration, and was washed with methanol and n-hexane respectively. Alkanes and chloroform were extracted, the chloroform extract was concentrated and dropped into 150 mL of methanol for precipitation again, and 92 mg of a black solid was obtained by suction filtration, with a yield of 77%.

[0140] 1 H ...

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Abstract

The invention discloses an azepine-2,7-dione acceptor unit and its application, wherein the structure of the azepine-2,7-dione acceptor unit is represented by the following general formula (I) or general formula ( II) means: R1, R2 independently represent an alkyl chain; A1, A2, A3, A4, A5 independently represent an aromatic ring or an aromatic heterocyclic ring. The azepine-2,7-diketone acceptor unit of the present invention has strong electron-pulling ability, can effectively reduce the polymer band gap and adjust its energy level; has a good planar conjugated structure, strong intermolecular The force is conducive to the orderly accumulation of molecules, thereby improving the mobility of organic conjugated molecules and the energy conversion efficiency of corresponding organic solar cells based on this unit; the energy conversion efficiency (PCE) of polymer solar cells based on this unit ) up to 5.46%.

Description

1. Technical field [0001] The invention relates to an azepine-2,7-dione acceptor unit and its application. 2. Background technology [0002] With the rapid development of global industry and economy, human beings' demand for energy increases rapidly, and the energy crisis continues to aggravate. On the one hand, fossil fuels will eventually be exhausted, and new energy alternatives are urgently needed; on the other hand, the excessive use of fossil fuels seriously affects the global climate and environment. Solar cells can directly convert clean and renewable solar energy into usable electrical energy and have attracted much attention. Organic solar cells, as the third generation of solar cells, have developed rapidly in recent years. Among them, bulk heterojunction polymer solar cells have been extensively studied (G. Yu et al, Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-acceptor Heterojunctions. Science, 1995, 270, 1789-1791), and its...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C08G61/12H01L51/46
CPCC08G61/12C08G61/126C08G2261/334C08G2261/91C08G2261/3223C08G2261/3243C08G2261/1412C08G2261/18H10K85/151H10K85/40Y02E10/549
Inventor 丁俊
Owner 合肥市激子能源技术有限公司
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