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Organic dye sensitizer, preparation method and application in photoelectric conversion

A technology of organic dyes and sensitizers, used in organic dyes, organic chemistry, tin organic compounds, etc., can solve problems such as poor light, thermal and chemical stability

Inactive Publication Date: 2014-10-01
SHANGHAI YUNYI HEALTHCARE MANAGEMENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide an organic dye sensitizer, preparation method and application in photoelectric conversion in order to overcome the defects of existing organic dye sensitizers such as poor light, heat and chemical stability.

Method used

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  • Organic dye sensitizer, preparation method and application in photoelectric conversion
  • Organic dye sensitizer, preparation method and application in photoelectric conversion
  • Organic dye sensitizer, preparation method and application in photoelectric conversion

Examples

Experimental program
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Effect test

Embodiment 1

[0443]

[0444]1) Synthesis of intermediate A1: N-bromosuccinimide (1.60 g, 9 mmol) was added to 3-formylthiophene (1.0 g, 9 mmol) in 80 mL of N,N-dimethylformamide solution, react at room temperature for 2 days, then add 100 mL of water, and extract with ethyl acetate (100 mL, 3 times), the organic layer is concentrated, and the silica gel column (petroleum ether: acetic acid Ethyl ester=50:1) to obtain 1.9 g of compound A1 with a yield of 78.5%. 1 H-NMR (400MHz, DMSO-d 6 ) δ: 7.476(s, 1H), 9.722(s, 1H). ESI-MS[M+H] + :267.8.

[0445] 2) Synthesis of intermediate B1: Add compound A1 (538 mg, 2 mmol), thiophene-2-boronic acid (256 mg, 2 mmol), tetrakistriphenylphosphine palladium (232 mg, 0.2 mmol) into a 100 ml flask mol) and tetrahydrofuran: water (5:1) 24 ml. Under nitrogen protection, the mixture was reacted at 70°C for 8 hours, cooled to room temperature, concentrated to remove the solvent, and silica gel column chromatography (petroleum ether: ethyl acetate = 50:...

Embodiment 2

[0452]

[0453]

[0454] 1) Synthesis of intermediate I: Add 1,1,7,7-tetramethyljulonidine (91.6 mg, 0.4 mmol), N-bromosuccinimide (71.2 g, 0.4 mmol) and 12 ml of dichloromethane. Under nitrogen protection, the mixture was reacted at room temperature for 16 hours, 12 ml of water was added, extracted with dichloromethane (15 ml, 3 times) and concentrated to remove the solvent to obtain 105 mg of compound I, LC-MS purity: 100%, yield 85.1 %. 1 H-NMR (400MHz, DMSO-d 6 )δ: 1.254(s, 12H), 1.733(t, 4H), 3.121(t, 4H), 7.083(s, 2H), ESI-MS (M+H + ): 310.0.

[0455] 2) Synthesis of Intermediate J: Compound I (92.4 mg, 0.3 mmol), double pinacol borate (152 mg, 0.6 mmol), potassium acetate (88.3 mg, 0.9 mmol) were added to a 50 ml flask ), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (Pd(dppf)Cl 2 ) (24 mg, 0.03 mmol) and 20 ml of dioxane. Under the condition of nitrogen protection, the mixture was reacted at 85°C for 16 hours, concentrated to remove the solvent...

Embodiment 3

[0466]

[0467]

[0468] 1) Synthesis of intermediate Y: Add thieno[3,2-b]thiophene (140 mg, 1 mmol), N-bromosuccinimide (480 g, 0.9 mmol) and Dichloromethane 12 ml. Under the condition of nitrogen protection, the mixture was reacted at room temperature for 16 hours, 12 ml of water was added, extracted with dichloromethane (15 ml, 3 times) and concentrated to remove the solvent to obtain 180 mg of intermediate Y. Yield 82.1%. ESI-MS (M+H + ): 219.8.

[0469] 2) Synthesis of intermediate Z: Add compound Y (175.2 mg, 0.8 mmol), compound 3 (182.4 mg, 0.96 mmol), potassium carbonate (331 mg, 2.4 mmol), tetratriphenyl Phosphopalladium (92.6 mg, 0.08 mmol), THF 20 mL and water 6 mL. Under the condition of nitrogen protection, the mixture was reacted at 68°C for 16 hours, concentrated to remove the solvent, and then separated by silica gel column chromatography (petroleum ether) to obtain 170 mg of intermediate Z. Yield 74.8%. 1 H-NMR (400MHz, DMSO-d 6 )δ: 7.196(d,1H), 7...

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PUM

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Abstract

The invention discloses an organic dye sensitizer, a preparation method and an application of the organic dye sensitizer in photoelectric conversion. The invention provides an organic dye sensitizer having the general formula as shown in formula I, wherein A is an electron-deficient unit, which is an electron acceptor; D is an electron-rich unit, which is an electron donor; N is an electron neutral organic structural unit, which has no significant ability to push and pull the electron; pion is a conjugate structural unit for bonding; Ar is conjugated aromatic ring system chromophoric units or a conjugated combination of two or more of structural units; B refers to a structural unit formed by bonding a nanometer porous surface of the dye-sensitized cell photoanode and transporting electrons excited by irradiating dye-sensitizing agent molecules with the visible and ultraviolet light to form current; and n is 1,2,3,4,5 or 6.

Description

technical field [0001] The invention relates to an organic dye sensitizer, a preparation method and an application in photoelectric conversion. Background technique [0002] The potential crisis of energy and the continuous deterioration of the ecological environment make the development of new energy and renewable energy including solar energy a major issue worldwide. All life on earth is based on solar energy (realized through photosynthesis of algae plants) ), electric energy is a safe and effective form of energy widely used in human society (realized by various power stations, batteries and electrical appliances), photoelectric energy conversion and energy storage technology is a fundamental energy solution. At present, the most important part of photovoltaic cell technology research and material development is still carried out around crystalline silicon. Silicon-based solar cells have high requirements for material purity and expensive equipment and production costs; ...

Claims

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Application Information

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IPC IPC(8): C09B23/04C09B57/00C07D495/04C07D487/04C07D417/10C07D417/14C07D409/14C07D333/24C07F7/10C07F5/04C07F7/22C07D333/28H01G9/20
CPCC09B57/00C09B17/04C09B23/105C09B23/148C09B57/001C09B57/004C09B57/008C09B69/109H01G9/2031H01G9/2059Y02E10/542Y02E10/549H10K85/655H10K85/636H10K85/657H10K85/40
Inventor 朱文峰许祖盛高俊雄王广印张国亮高柏涛鲍静郑广兵王振平陈浩吴添智黄福新林逍陈龙
Owner SHANGHAI YUNYI HEALTHCARE MANAGEMENT
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