Spirofluorene derivative and preparation method and application thereof

The technology of a derivative and spirofluorene is applied in the field of spirofluorene derivatives and the preparation thereof, and achieves the effects of satisfying use requirements, easy preparation method and high purity

Active Publication Date: 2013-05-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In 1986, Dr. Deng Qingyun of Kodak made a double-layer film composed of a derivative of tetracarboxyperylene and copper phthalocyanine, and connected the two layers of film to two electrode

Method used

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  • Spirofluorene derivative and preparation method and application thereof
  • Spirofluorene derivative and preparation method and application thereof
  • Spirofluorene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Synthesis of Compound II

[0065] Add 4,7-dibromobenzothiadiazole (8.82g, 30mmol), 4-hexyl-2-tributyltinthiophene (34.29g, 75mmol) in a 200ml single-necked bottle, N 2 Under protection, adding Pd(PPh 3 ) 4 (347mg, 0.3mmol), injected into 110mL of toluene, refluxed at 115°C for 24h. Stop the reaction, cool to room temperature, add 150mL water, extract three times with chloroform, combine the organic phases, and use anhydrous Na 2 SO 4 Dry, filter, and spin-dry to obtain a crude product, which is separated by silica gel column chromatography (trichloromethane / petroleum ether=1:3 as eluent) to obtain compound II (11.67 g, 83%).

[0066] Its structure is shown in the following formula:

[0067]

Embodiment 2

[0069] Synthesis of compound III

[0070] In a 250ml two-necked round bottom bottle, add compound II (5.63g, 12mmol), N 2 Inject 100mL of 1,2-dichloroethane under protection, N',N'-dimethylformamide (0.94mL, 12.6mmol), inject phosphorus oxychloride (1.10mL, 12.6mmol) at 0°C, and reflux Reaction 12h. Stop the reaction, cool to room temperature, pour the reaction solution into 100mL 2M sodium acetate aqueous solution, stir for 2h, extract with chloroform, wash twice with water, and wash with anhydrous Na 2 SO 4 Dry, filter, and spin-dry to obtain a crude product, which is separated by silica gel column chromatography (trichloromethane / petroleum ether=1:1 as eluent) to obtain compound III (5.00 g, 84%).

[0071] Its structural formula is as follows:

[0072]

Embodiment 3

[0074] Synthesis of Compound IV

[0075] In a 150 mL single-necked bottle, compound III (4.52 g, 9.1 mmol) was dissolved in 100 mL of chloroform, and NBS (1.72 g, 9.56 mmol) was added to the reaction solution five times, and reacted at room temperature for 12 h in the dark. Pour the reaction solution into 200mL water, extract with chloroform, combine the organic phases, and use anhydrous Na 2 SO 4 Dried, filtered, and spin-dried to obtain a crude product, which was recrystallized from chloroform and ethanol (1:1) to obtain compound IV (5 g, 95%). 1 H NMR (400MHz, CDCl 3 ): δ10.11(s, 1H), 8.07(s, 1H), 7.97(d, 1H), 7.83(s, 1H), 7.80(d, 1H), 3.03(t, 2H), 2.64(t, 2H), 1.81 (m, 2H), 1.67 (m, 2H), 1.34-1.44 (m, 12H), 0.92 (m, 6H).

[0076] Its structural formula is as follows:

[0077]

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Abstract

The invention discloses a spirofluorene derivative. The structure of the spirofluorene derivative is shown as a formula (I); and in the formula (I), R1, R2, R3 and R4 are end group receptor groups and are independently selected from groups shown as a formula (I-a), a formula (I-b) or a formula (I-c).The spirofluorene derivative has a strong absorbing ability to visible light, and can be used as a small molecular donor material and applied in the field of organic solar energy. The invention also discloses a preparation method for the spirofluorene derivative. The spirofluorene derivative is obtained by using 4,7-dibromobenzothiadiazole and 4-hexyl-2-tributyltin thiophene as initial raw materials through Stille coupling reaction, Vilsmeier-Harker reaction, bromination reaction, Suzuki coupling reaction and Knoevenagel condensation reaction sequentially.

Description

technical field [0001] The invention belongs to the technical field of organic solar cell materials, and in particular relates to a spirofluorene derivative and a preparation method and application thereof. Background technique [0002] Solar energy is an inexhaustible, clean and pollution-free renewable energy source for human beings. A solar cell is a device that directly converts light energy into electrical energy through the photoelectric effect or photochemical effect, including inorganic solar cells and organic solar cells. [0003] Organic solar cells are a new type of solar cells under research. Compared with inorganic solar cells, they have the advantages of light weight, low price, solution processing, high mechanical flexibility, and can be made into flexible large-area devices. Dating back to 1958, Kearns and Calvin sandwiched the magnesium phthalocyanine dye layer between two electrodes with different work functions to support the first organic photoelectric c...

Claims

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Application Information

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IPC IPC(8): C07D417/14H01L51/46
CPCY02E10/549
Inventor 方俊锋叶丹丹张文俊胡钊闵超
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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