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Phenothiazines dye used for dye sensitization solar battery

A dye sensitization and phenothiazine technology, applied in thiazine dyes, organic dyes, circuits, etc., can solve the problems of low color intensity, high cost, and limited application

Active Publication Date: 2008-02-20
JIANGSU AOLUNDA HIGH TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of noble metals in this type of compound, the cost of this type of dye is relatively high, and the color intensity is low, which limits its application

Method used

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  • Phenothiazines dye used for dye sensitization solar battery
  • Phenothiazines dye used for dye sensitization solar battery
  • Phenothiazines dye used for dye sensitization solar battery

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of N-butyl-3-cyanoacrylate-phenothiazine

[0038] All reactions were carried out in a dry environment.

[0039] (1) Synthesis of N-butyl-3-formyl-phenothiazine

[0040]

[0041] Dissolve 1.0g (3.92mmol) of N-butyl-phenothiazine in 15ml of chloroform, add 548mg of DMF (7.51mmol), stir vigorously at room temperature, and slowly add 2.3g of POCl 3 (15 mmol). Then heat up to reflux state and keep warm for 24 hours. After the reaction, the acetone was evaporated as much as possible by a rotary evaporator. Using dichloromethane as eluent to carry out column separation and purification on a silica gel column to obtain 900 mg (3.18 mmol) of compound N-butyl-3-formyl-phenothiazine with a yield of 81.1%. NMR 1 H-NMR (400MHz, Acetone-d6): δ (ppm): 0.87 (3H, t), 1.42-1.48 (2H, m), 1.73-1.80 (2H, m), 4.01 (2H, t), 6.90 ( 1H, t), 7.07 (1H, d, J = 8.0Hz), 7.13 (2H, m), 7.21 (1H, t), 7.57 (1H, d, J = 1.9Hz), 7.70 (1H, ddJ 1 =1.9Hz,J 2 =1.9Hz), 9.79(1H, s). Mass Spe...

Embodiment 2

[0046] Synthesis of N-butyl-3-(5-methylenerhodenine)-phenothiazine

[0047]

[0048] Add 120mg (0.42mmol) N-butyl-3-formyl-phenothiazine and 90mg (0.51mmol) rhodanine to 20ml acetic acid, and reflux for 3h in the presence of 50mg (0.65mmol) ammonium acetate. After cooling down to room temperature, it was poured into 50 ml of ice water, and the solid was collected by filtration. Use dichloromethane:methanol=7:1 (volume ratio) solution as the eluent to carry out column separation and purification on the silica gel column to obtain the compound N-butyl-3-(5-methylene rhodanine acid group) -Phenothiazine 140 mg (0.32 mmol), yield 76.2%. NMR 1 H-NMR (400MHz, Acetone-d6): 0.90 (3H, t), 1.43-1.49 (2H, m), 1.76-1.79 (2H, m), 4.00 (2H, t), 4.84 (2H, s), 6.97(1H, t), 7.07(1H, d, J=8.1Hz), 7.13(1H, d, J=7.6Hz), 7.17(1H, d, J=8.0Hz), 7.20(1H, t), 7.85(1H,d,J=2.0Hz), 7.47(1H,dd,J 1 =2.1Hz,J 2 =2.1Hz), 7.68 (1H, s). Mass Spectrometry TOF MS ES + : Found m / z 456.0632.Calc.for C 22...

Embodiment 3

[0050] Synthesis of N-butyl-3-[4-(2-cyanoacrylate)phenyl-1-vinyl]-phenothiazine

[0051] All reactions were carried out in a dry environment.

[0052] (1) Synthesis of N-butyl-3-hydroxymethyl-phenothiazine

[0053]

[0054] Add 81mg (2.13mmol) of sodium borocyanide to a mixed solvent of 10ml of ethanol and 10ml of dichloromethane, then add 600mg (2.12mmol) of N-butyl-3-formyl-phenothiazine in one go, at room temperature Stir for 1h. After the reaction was completed, 20ml of water was added and stirred vigorously, then extracted 3 times with dichloromethane, the collected organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain 592mg of the compound N-butyl-3-hydroxymethyl-phenothiazine (2.07 mmol), yield 97.6%. NMR 1 H-NMR (400MHz, Acetone-d6): δ (ppm): 0.87 (3H, t), 1.40-1.45 (2H, m), 1.70-1.74 (2H, m), 3.87-3.91 (2H, t), 4.10(1H, t), 4.49(2H, d, J=5.8Hz), 6.88(1H, t), 6.93(1H, d, J=8.3Hz), 6.97(1H, d, J=8.2Hz)...

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Abstract

The invention relates to a phenothiazine dye used in dye-sensitized solar cells and pertains to photoelectric transformation material application field. The structure of the dye is that the phenothiazine and derivatives thereof are taken as EDS and contains different amount of aromatic cyclic structure unit or multiple olefin structure adjustable with absorption spectrum and fluorescence emission spectrum and as bridged chain to connect the organic dye with different electron absorbing groups. Since the phenothiazine as chromophore group has good electron supply capacity, the aromatic cyclic structure unit or the olefin structure can function to broaden absorption range of visible light of the dye and electron transmission capacity and by connecting with the electron absorbing group of different types, the dye has good light, thermal and chemical stability and photoelectric transformation property. The dye is applicable in dye-sensitized nanometer solar cells as organic photosensitive dye.

Description

technical field [0001] The invention belongs to the application field of organic dyes in photoelectric conversion technology, and specifically relates to the application of a class of phenothiazine derivative organic functional dyes as photosensitizers in dye-sensitized solar cells. Background technique [0002] Dye-sensitized nanocrystalline solar cells were first proposed in 1991 by Professor M.Grtzel of Switzerland as a new type of solar energy-to-electricity conversion device. Its structure is to sinter a layer of nanoporous TiO on a conductive glass substrate 2 film, and adsorb a layer of photosensitive dye on it as a photoanode, and the cathode is composed of Pt-coated conductive glass, I 3 - / I - The redox pair exists between the cathode and the anode as the electrolyte or uses a solid electrolyte to replace I 3 - / I - redox pair. This type of battery has become a kind of photoelectric conversion device with application prospects due to its advantages such as ...

Claims

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Application Information

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IPC IPC(8): C09B21/00H01L51/46H01L51/48H01G9/20H01M14/00
CPCY02E10/542Y02E10/549
Inventor 杨希川田海宁孙立成
Owner JIANGSU AOLUNDA HIGH TECH IND
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