Organic dye sensitizer based on dibenzophenothiazine as well as preparation method and application of organic dye sensitizer

A technology of benzophenothiazine and organic dyes, which is applied in the field of organic photoelectric functional materials, can solve the problems of complex synthesis, toxicity, and low yield, and achieve the effects of common and easy-to-obtain raw materials, low production costs, and high absorption coefficient

Pending Publication Date: 2021-08-06
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The complex synthesis and low yield of metal complex dyes greatly increase the difficulty of synthesis, and the raw materials and their products have certain toxicity. The scarcity of rare metal resources also increases the cost and limits further development to a certain extent.

Method used

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  • Organic dye sensitizer based on dibenzophenothiazine as well as preparation method and application of organic dye sensitizer
  • Organic dye sensitizer based on dibenzophenothiazine as well as preparation method and application of organic dye sensitizer
  • Organic dye sensitizer based on dibenzophenothiazine as well as preparation method and application of organic dye sensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Use hexyl chain to modify triphenylamine as donor, phenyl is the preparation method of dibenzophenothiazine-based organic dye molecule P1 of π spacer, the synthetic route of described preparation method is as follows:

[0039]

[0040] The preparation method comprises the following steps:

[0041] 1. Preparation of compound 1: under a nitrogen atmosphere, put 1,2'-dinaphthylamine (1.35g, 5mmol), sulfur (0.32g, 5mmol) and iodine (0.33g, 1.3mmol) in a 250ml round bottom In the flask, 30 ml of o-dichlorobenzene as a solvent was added, and the reaction mixture was raised to 180° C., kept at this temperature for 30 minutes, and then cooled to room temperature. After the reaction was complete, the dark reaction mass was dissolved in a small amount of acetone and enough petroleum ether was added to produce two layers. After separation of the layers, the dark solution was extracted several times with fresh warm petroleum ether and the petroleum ether layers were combined. ...

Embodiment 2

[0048] Modified phenyl carbazole with hexyl chain as donor, thiophene is the preparation method of dibenzophenothiazine-based organic dye molecule P2 of π spacer, the synthetic route of described preparation method is as follows:

[0049]

[0050] The preparation method comprises the following steps:

[0051] The synthesis steps of compounds 1, 2, and 3 are the same as those in Example 1.

[0052] Preparation of compound 4b: under nitrogen atmosphere, compound 3 (541 mg, 1 mmol), (5-formylthiophen-2-yl) boronic acid (180 mg, 1.2 mmol), K 2 CO 3 (345mg, 2.5mmol), Pd[P(C 6 h 5 ) 3 ] 4 (50mg, 0.05mmol) and TBAB (96.6mg, 0.3mmol) were placed in a three-necked flask, poured into 15ml of tetrahydrofuran solvent, heated to 85°C and refluxed for 13h. When the latter should be complete, add water to quench the reaction. After the reaction solution was cooled to room temperature, it was extracted 3 times with DCM and brine, and dried with NaSO4. The crude product was then pur...

Embodiment 3

[0056] The absorption spectrum of the P1 dye: the organic dye with hexyl chain modified triphenylamine as the electron donor, dibenzophenothiazine as the core group of the π bridge, and the benzene ring as the π spacer have a maximum absorption peak of ultraviolet-visible light at about 560nm. When the molar absorptivity (ε) can reach up to 6.8×10 4 L·mol -1 cm -1 , see figure 1 . The sensitizer prepared by the invention has stable structure, proper energy gap and high absorption coefficient.

[0057] The preparation method of the sensitized solar cell based on P1 dye comprises the following steps: the FTO substrate is coated with a detergent on the surface and scrubbed, washed with water and then placed on a film rack, and then the film rack is put into a beaker, and used in turn. Ionized water, absolute ethanol, and acetone were sonicated for 15 minutes each. After the end, the cleaned substrate was taken out and dried in an oven at 110°C for 1 hour. The conductive surfa...

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Abstract

The invention discloses an organic dye sensitizer based on dibenzophenothiazine and a preparation method of the organic dye sensitizer; the molecule adopts alkyl chain modified triphenylamine, phenyl carbazole or indole as an electron-donating group and dibenzophenothiazine as a core group, a long carbon chain, phenyl, thiophene or furan as a pi spacer is introduced to the N atom of phenothiazine, cyano acrylic acid is used as an anchor group; dibenzophenothiazine is adopted as a core group, and the non-planar butterfly conformation of dibenzophenothiazine can fully inhibit molecular aggregation and elicitor formation; and meanwhile, the energy gap can be adjusted, the spectral response range can be improved, phenyl, thiophene or furan is introduced to serve as a pi spacer, a conjugated system can be further expanded, the spectral response range is widened, intramolecular charge transfer is enhanced, effective injection of electrons is ensured, the device performance is improved, and the organic dye sensitizer can be used for preparing a dye-sensitized solar cell.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, in particular to a class of organic dye sensitizers based on dibenzophenothiazine and its preparation method and application. Background technique [0002] Energy is the initial driving force to promote the progress of human society, but with the rapid development of the global economy, most of the traditional natural resources are non-renewable resources, so among all renewable energy sources, solar energy is inexhaustible and inexhaustible. , clean and environmentally friendly, and the characteristics of small regional dependence have been extensively studied. [0003] The third-generation solar cells mainly include dye-sensitized solar cells, organic solar cells and perovskite solar cells. Dye-sensitized solar cells work by mimicking the process of photosynthesis in plants to convert solar energy into electricity. DSSC is the only organic solar cell that ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/14H01G9/20
CPCC07D279/14H01G9/20Y02E10/542
Inventor 许文娟是凯航郭娇王鹤然密保秀
Owner NANJING UNIV OF POSTS & TELECOMM
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