Rhodanine derivative and application thereof

A derivative and straight chain technology, applied in the field of rhodanine derivatives, can solve the problems of high price and complicated preparation process of dye sensitizers, and achieve the effects of low synthesis cost, easy preparation and cost reduction

Inactive Publication Date: 2012-07-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The photosensitizing dye with the best photoelectric conversion efficiency so far is bipyridyl ruthenium complex (about 12%), but because ruthenium is expensive as a rare metal, and the preparation process of the dye sensitizer is more complicated

Method used

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  • Rhodanine derivative and application thereof
  • Rhodanine derivative and application thereof
  • Rhodanine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0038] d. Preparation of photoanode: Brush a layer of TiO on the FTO conductive glass by screen printing (0.5×0.5cm) 2 Slurry, bake at 125°C for 6 minutes, after cooling, apply another layer, bake at 125°C for 6 minutes, apply two layers in total, then slowly heat up to 450°C and bake for 15 minutes, then heat up to 500°C for 15 minutes, cool to room temperature, use 20mM TiCl 4 The aqueous solution was treated at room temperature for 12 hours, washed twice with water and ethanol respectively, baked at 450°C for 30 minutes, and soaked in the dye solution (that is, prepared by step c) after cooling. Take it out after 12 hours, wash with the solvent used to soak the dye, and blow dry.

[0039] e. Electrolyte preparation: prepare 0.05M I 2 , 0.15M LiI, 0.1M DMPII and 0.5M TBP solution 10mL.

[0040] f. Encapsulation of the battery: on TiO adsorbed with dye 2 A thermosetting adhesive tape sealing ring is pasted around the membrane, and the conductive side of the opposite elect...

Embodiment 1

[0048]

[0049] Add rhodanine (2.66g, 20mmol), malononitrile (1.32g, 20mmol), sodium acetate (1.64g, 20mmol) and absolute ethanol (60ml) into a 100ml three-necked flask, and heat to reflux for 12h under the protection of Ar. After the reaction was completed, the solvent ethanol was removed by rotary evaporation, and the remaining solid was extracted three times with dichloromethane, the organic phases were combined and dried with anhydrous magnesium sulfate, and the dichloromethane was removed by rotary evaporation, and then recrystallized with absolute ethanol to obtain 1.98 g of the product , yield 60%.

[0050] 1 H NMR (400MHz, DMSO) δ: 3.78 (s, 2H).HR-MS (EI) calculated for C 6 h 3 N 3 OS: 163.9919, found: 163.9918.

[0051]

[0052] In 250ml there-necked flask, add phenothiazine (10g, 50mmol), 5g sodium hydroxide (5g, 0.1mol) and DMSO (100ml), then add 1.6g tetra-n-butylammonium bromide (1.6g, 5mmol), react Stir at room temperature for 30 min. 1-Bromooctane (1...

Embodiment 2

[0061]

[0062] Add p-iodophenol (8.8g, 40mmol), 1-bromooctane (8ml, 44mmol), potassium carbonate (10.04g, 80mmol) and potassium iodide (6g, 40mmol) into a 250ml three-neck flask. Under the protection of Ar, 80ml of DMF was added, and the temperature was raised to 90°C and the reaction was stirred for 24h. After the reaction, the reaction solution was poured into ice water and stirred until the ice completely melted, CH 2 Cl 2 Extraction, washing with water, drying the organic phase with anhydrous sodium sulfate, spin-drying the solvent, and then performing column chromatography (PE). 9.6 g of colorless liquid was obtained with a yield of 72.3%.

[0063] 1 H NMR (400MHz, CDCl 3 )δ: 7.94(s, 2H), 6.68(s, 2H), 4.10(s, 2H), 1.73(s, 2H), 1.43(s, 2H), 1.28(d, J=19.9Hz, 8H), 0.89(s, 3H).

[0064]

[0065] In a 250ml three-necked flask, add diphenylamine (1.4g, 15mmol), 3 (25.2g, 76mmol), o-phenanthroline (2.97g, 15mmol), cuprous chloride (2.87g, 15mmol), potassium hydroxi...

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PUM

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Abstract

The invention relates to a rhodanine derivative and an application thereof. In the rhodanine derivative, a group containing a multi-ring aromatic ring group or/and a multi-ring heteroaromatic ring group is taken as an electron donor, and 2-(1',1'-dicyan)rhodanine is taken as an electron acceptor; or a group containing a multi-ring aromatic ring group or/and a multi-ring heteroaromatic ring group is taken as an electron donor, 2-(1',1'-dicyan)rhodanine is taken as an electron acceptor, and a conjugated heteroaromatic ring group is taken as a bridging group. The obtained rhodanine derivatives have unique photoelectric chemical performance, and can be taken as photosensitizers of dye-sensitized solar cells.

Description

technical field [0001] The present invention relates to a rhodanine derivative and its use, in particular to a malononitrile-based rhodanine derivative and its use. Background technique [0002] With the rapid development of human industrial civilization and market economy, mineral non-renewable resources such as coal, oil and natural gas are increasingly depleted. The resulting energy crisis and environmental pollution have become global problems that need to be solved urgently. Therefore, people urgently need to find other new alternative energy sources. Dye-sensitized solar cells (B.O'Regan, M. Nature, 1991,353,737-740), because of its advantages such as low cost and simple manufacture and potential practical value. [0003] Dye-sensitized solar cells (DSSCs) are usually composed of nanoporous semiconductor oxide films (TiO 2 ), dye sensitizer, redox electrolyte (I - / I 3- ) and the counter electrode (Pt), among which the ability to absorb sunlight and transport ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D277/34C07D417/14C09B23/04H01G9/042H01L51/46
CPCY02E10/549
Inventor 花建丽毛江毅郭福领贺楠楠武文俊应伟江田禾
Owner EAST CHINA UNIV OF SCI & TECH
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