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Michlers ketone-cyano groups organic dyestuff and synthesis method thereof

A technology of organic dyes and synthesis methods, applied in the field of solar cells, can solve the problems of high price of sensitizers and inability to popularize

Inactive Publication Date: 2010-06-09
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the problem that the ruthenium-based bipyridine complex dye sensitizer is expensive and cannot be popularized, and to provide a new type of high-efficiency photosensitizer of Michler's ketone-cyano organic dye and its synthesis method

Method used

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  • Michlers ketone-cyano groups organic dyestuff and synthesis method thereof
  • Michlers ketone-cyano groups organic dyestuff and synthesis method thereof
  • Michlers ketone-cyano groups organic dyestuff and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0061] The synthetic route of novel Michler's ketone-cyano organic dye I:

[0062]

[0063] The synthesis method is:

[0064] Synthesis of Mie's Phosphate

[0065] Add 2.68g of Michler's ketone, 0.3g of sodium borohydride, 12mL of isopropanol and 0.7mL of water into a 50mL flask, heat to reflux for 4 hours, cool to room temperature, filter and wash to obtain Michler's alcohol, and recrystallize from ethanol to obtain pure rice Alcohol, productive rate 90%; Under the protection of nitrogen, add 2mL triethyl phosphite in 0.54g Michaelis alcohol (2.0mmol) at 0 ℃, then add 0.52g iodine (2.0mmol) in three batches, add Afterwards, the reaction mixture was continued to react at 0°C for 10 min, and at room temperature for 12 hours, adding 10% KOH aqueous solution and stirring for 30 min, separating the organic layer, extracting the aqueous layer with chloroform, combining the organic layers, washing with saturated brine, anhydrous Dried over magnesium sulfate, filtered and distil...

Embodiment 2

[0076] The synthetic route of novel Michler's ketone-cyano organic dye II:

[0077]

[0078] The synthesis method is:

[0079] Synthesis of Mie-substituted p-bromophenylalkenes 1

[0080] Under the protection of nitrogen, add 20 mL of THF and 0.66 g of potassium tert-butoxide to 1.5 g of Mie's phosphate (3.6 mmol) at 0°C, react at this temperature for 1 hour after the addition, and add 0.56 g of p-bromobenzene dropwise Dissolve formaldehyde in 10mL of THF solution, add saturated ammonium chloride aqueous solution after reacting at room temperature for 24 hours, separate the organic layer, extract with ethyl acetate, combine the organic layer, dry the organic layer with anhydrous magnesium sulfate, filter, The solvent was evaporated, and the solid was recrystallized from petroleum ether (60°C-90°C) to obtain Mie-substituted p-bromophenylalkene 1 with a yield of 60%.

[0081] Synthesis of Mie-substituted vinylphenylboronic acid 3

[0082] Under the protection of nitrogen, ...

Embodiment 3

[0090] The synthetic route of novel Michler's ketone-cyano organic dye III:

[0091]

[0092] The synthesis method is:

[0093] Synthesis of Mie-substituted p-bromophenylalkenes 1

[0094] Under the protection of nitrogen, add 20 mL of THF and 0.66 g of potassium tert-butoxide to 1.5 g of Mie's phosphate (3.6 mmol) at 0°C, react at this temperature for 1 hour after the addition, and add 0.56 g of p-bromobenzene dropwise Dissolve formaldehyde in 10mL of THF solution, add saturated ammonium chloride aqueous solution after reacting at room temperature for 24 hours, separate the organic layer, extract with ethyl acetate, combine the organic layer, dry the organic layer with anhydrous magnesium sulfate, filter, The solvent was evaporated, and the solid was recrystallized from petroleum ether (60°C-90°C) to obtain Mie-substituted p-bromophenylalkene 1 with a yield of 60%.

[0095] Synthesis of Mie-substituted p-thiophene phenylalkenes 2

[0096] Weigh 1.08g of activated magnesiu...

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Abstract

The invention provides a novel Michler ketone-cyan organic dye and a synthetic method thereof. The dye derives from Michler ketone, and has the structural formulae which represent Michler ketone-cyanorganic dye compounds 1, 2, 3, 4 and 5, respectively. Each molecule of the dye comprises two nitrogen containing groups, namely, the structural feature of double electron-donating groups. Accordingly,the molecules can be oxidized and deacidized easily, and have better capability of donating electrons and the capability of trapping electrons from electrolyte more quickly. The dye extends the design thought of organic photosensitizers, and enriches the research content of dye sensitization solar batteries, thereby having very important significances for improving the photoelectric transformation efficiency of organic solar batteries and reducing the cost of batteries both in theory and practice. The synthetic step is short, the process is simple; the cost is low and the yield is high.

Description

[0001] [Technical Field]: The present invention belongs to the technical field of solar cells, and particularly relates to a synthesis route and synthesis method of organic dye molecules with two nitrogen-containing groups that can be applied in organic dye-sensitized solar cells. The novel Michler's ketone-cyano double-donating group organic dye is a class of organic photosensitizer with excellent performance, and can be applied in organic dye-sensitized solar cells. 【Background technique】: [0002] With the increasingly prominent issues of energy and environmental protection, finding and utilizing clean and renewable energy has become one of the urgent tasks facing mankind. Solar cells that directly convert solar energy into electrical energy do not pollute the environment during the energy conversion process, which can not only effectively alleviate the energy shortage problem, but also meet my country's strategic goal of sustainable development. [0003] Commercialized sol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00H01L51/54
Inventor 薛松刘永康张璐王忠原山珊
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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