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Double-phenothiazine-based dye, and preparation method and application thereof

A phenothiazine-based dye technology, which can be used in thiazine dyes, methine-based/polymethine-based dyes, organic dyes, etc., can solve the difficulty of separation and purification of ruthenium polypyridine complexes, reduce large-scale practical application, and limit the cost of DSSCs And other issues

Inactive Publication Date: 2011-01-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ruthenium is a rare and noble metal, and the separation and purification of the corresponding ruthenium polypyridine complex is also quite difficult, which limits the cost reduction and large-scale practical application of DSSCs in the future.

Method used

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  • Double-phenothiazine-based dye, and preparation method and application thereof
  • Double-phenothiazine-based dye, and preparation method and application thereof
  • Double-phenothiazine-based dye, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Synthesis of 1,6-bis-(3-cyanoacrylate phenothiazinyl)-n-hexane

[0071] All reactions were carried out in a dry environment under nitrogen protection

[0072] (1) Synthesis of 1,6-bisphenothiazinyl n-hexane

[0073]

[0074] Dissolve 1.99g (10mmol) of phenothiazine in 15ml of DMSO, add 2.24g (40mmol) of KOH, and vigorously stir at room temperature for 20min. Then 1.22g (5mmol) of 1,6-dibromohexane was added dropwise, and the reaction was continued for 48h. After the reaction was completed, it was poured into an ice-water mixture and stirred vigorously for 30 min, filtered, and the solid was dissolved in dichloromethane, washed 3 times with water, and the organic phase was dried, and the crude product was recrystallized to obtain 2.01 g (4.18 mmol) of the product, with a yield of 83.6%. . Melting point: 163-165°C.

[0075] (2) Synthesis of 1,6-bis-(3-formylphenothiazinyl)-n-hexane

[0076]

[0077] Add 1.23g (8mmol) POCl to 1-20 parts of 731mg (10mmol) DMF in ...

Embodiment 2

[0082] Synthesis of N-ethyl-3-cyanoacrylate-phenothiazine

[0083] All reactions were carried out in a dry environment under nitrogen protection

[0084] (1) Synthesis of N-ethylphenothiazine

[0085]

[0086]Dissolve 1.99g (10mmol) of phenothiazine in 15ml of DMSO, add 2.24g (40mmol) of KOH, and stir at room temperature for 20min. Then 1.64g (15mmol) of bromoethane was added dropwise, and the reaction was continued for 48h. Pour into ice-water mixture and stir for 10 min, filter, dissolve the solid in dichloromethane, wash 3 times with water, dry the organic phase, and recrystallize the crude product to obtain 1.70 g (7.48 mmol) product with a yield of 75%. Melting point: 104-105°C.

[0087] (2) Synthesis of N-ethyl-3-formyl-phenothiazine

[0088]

[0089] Add 1.23g (8mmol) POCl to 731mg (10mmol) DMF of 1-20 parts in Bingyu 3 , and then remove the ice bath, return to room temperature, and stir the reaction for 1h. Then, 455 mg (2 mmol) of N-ethylphenothiazine diss...

Embodiment 3

[0094] The ultraviolet-visible absorption spectrum / fluorescence spectrum test of embodiment 1 and embodiment 2 dyestuffs, ultraviolet-visible absorption spectrum and fluorescence emission spectrogram are respectively image 3 , Figure 4 shown.

[0095] Solvent: THF

[0096] Concentration: 2×10 -5 m

[0097] Temperature: room temperature

[0098] Instruments: Shimadzu UV-2450 UV-visible scenery photometer, Hitachi F-4500 fluorescence spectrometer

[0099] The maximum ultraviolet / visible absorption wavelength and the maximum fluorescence emission wavelength (nm) data comparison of the dyestuff in the embodiment 1 and 2 of table 1, the data obtained are summarized in table 1

[0100] Table 1

[0101] dye

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Abstract

The invention discloses a double-phenothiazine-based dye, and a preparation method and application thereof, and belongs to the field of application of photoelectric conversion materials in fine chemical engineering. In the method, double phenothiazines and derivative units thereof are connected by alkyl groups to form a two-electron donor; on such a basis, conjugate phi bridges are extended by double bonds respectively; tail ends are connected with cyanoacetic acids as electron acceptors; and a series of dyes are synthesized by the method. As the double-phenothiazine-based dye has higher bonding capacity compared with TiO2 and is effectively prevented from being aggregated on the surface of the TiO2, the double-phenothiazine-based dye has higher performance compared with a single-phenothiazine-based dye under the same condition. The double-phenothiazine-based dye has the characteristics of simple synthesis method and easily-obtainable raw materials, can replace an expensive noble-metal photosensitive dye difficult to prepare and purify, and effectively reduces the cost of dye sensitized solar cells.

Description

technical field [0001] The invention discloses a method for preparing a class of bisphenothiazine-based dyes and its application in dye-sensitized solar cells, which belongs to the application field of photoelectric conversion materials in fine chemical industry, and specifically relates to a class of bisphenothiazine-based dyes and their application. Design and synthesis of derivatives, and application of said dyes in dye-sensitized solar cells. technical background [0002] Dye-sensitized solar cells (DSSCs) were invented in 1991 by Swiss scientist M. A new type of device that converts solar energy into electrical energy is proposed and designed for the first time. Its composition generally consists of the following aspects: a photocathode with Pt-plated conductive glass as a substrate, a photoanode composed of a nanoporous oxide film adsorbed with a photosensitive dye and a transparent conductive substrate, an electrolyte filled between the two electrodes, and a sealed ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B21/00H01G9/20H01M14/00H01L51/42
CPCY02E10/542Y02E10/549C07D279/22C09B21/00C09B23/005C09B23/0058C09B23/105H01G9/2059C07D279/26C07D279/28Y02P70/50H10K85/652H10K85/657
Inventor 曹德榕彭锦安洪艳平汪凌云方晓明
Owner SOUTH CHINA UNIV OF TECH
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