Triphenylamine organic dye and synthesis method thereof

An organic dye and synthesis method technology, applied in the field of dye-sensitized solar cell sensitizers, can solve problems such as low photoelectric conversion efficiency, and achieve the effects of favorable electron transport, good application prospects and mild reaction conditions

Inactive Publication Date: 2019-11-08
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The introduction of the electron-withdrawing group thiazo[3,4-c]pyridine can adjust the energy level difference between HOMO and LUMO and red-shift the absorption spectrum, but the photoelectric conversion efficiency is low (HUA Y, WANG HD, ZHUX J, et al.New simple panchromatic dyes based on thiadiazolo [3, 4-c] pyridine unit for dye-sensitized solar cells [J]. Dyes and Pigments, 2014, 102; 196-203)

Method used

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  • Triphenylamine organic dye and synthesis method thereof
  • Triphenylamine organic dye and synthesis method thereof
  • Triphenylamine organic dye and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Synthesis of Dye FWD 9:

[0047] Synthesis of Compound 1: Dissolve 4-bromotriphenylamine (1.3030g, 4mmol) in anhydrous N,N-dimethylformamide (DMF) (9.3mL) under nitrogen atmosphere, and stir at 0°C for 15min , to this solution was added dropwise POCl 3 (8mL, 100mmol), the solution gradually turned blue-yellow and solid was produced, and continued to stir at 0°C for 15min, and then reacted the mixture at 100°C for 20h. After the reaction is complete, add water dropwise to the reaction system at 0°C, filter to obtain the filter residue, and filter the residue with CH 2 Cl 2 Extraction, the organic layer was washed with saturated NaCl aqueous solution, washed with anhydrous NaCl 2 SO 4Drying, rotary evaporation, PE / DCM as eluent, and column chromatography gave Intermediate 1 (light yellow crystal, 1.1353g), with a yield of 74.6%.

[0048] Synthesis of Compound 2: Under a nitrogen atmosphere, Intermediate 1 (1.2383g, 3.3mmol) and diethyl benzylphosphonate (1.5483g, 9.9...

Embodiment 2

[0061] Synthesis of Dye FWD10:

[0062] Synthesis of compound 7: 4-bromoaniline (1.4516g, 4.5mmol), 1-Boc-pyrrole-2-boronic acid (863.3mg, 4.1mmol), tetrakis(triphenylphosphine) palladium were added successively in a 250mL two-necked flask (284.3mg, 6%mmol), sodium carbonate (1.3037g, 13.5mmol), under the condition of nitrogen protection, solvent tetrahydrofuran (52mL) and water (13mL) were added respectively, and the reaction system was refluxed overnight. After the reaction is complete, add saturated NH 4 Cl solution with CH 2 Cl 2 Extraction, organic phase with anhydrous Na 2 SO 4 Drying, filtration, rotary evaporation, PE / DCM as eluent, column chromatography gave Intermediate 7 (white solid, 1.3061g), yield 70.7%

[0063] 1 H NMR (500MHz, CDCl 3 )δ (ppm): 7.34 (dd, J = 3.2, 1.8Hz, 1H), 7.25 (t, J = 7.6Hz, 4H), 7.20 (d, J = 8.5Hz, 2H), 7.11 (d, J = 7.7Hz, 4H), 7.04(d, J=8.5Hz, 2H), 7.01(t, J=7.3Hz, 2H), 6.21(t, J=3.3Hz, 1H), 6.17(dd, J=3.1, 1.8Hz,1H),1.41(s,9H).

...

Embodiment 3

[0073] Synthesis of Dye FHD 7:

[0074] Synthesis of compound 12: Under nitrogen atmosphere, intermediate 11 (1.3698g, 4mmol) and phenylselenite anhydride (1.7286g, 4.8mmol) were dissolved in chlorobenzene (30mL), and the reaction was refluxed for 12h. After the reaction is complete, add saturated NH 4 Cl solution with CH 2 Cl 2 Extraction, organic phase with anhydrous Na 2 SO 4 Drying, filtration, rotary evaporation, PE / DCM as eluent, and column chromatography gave intermediate 13 (white solid, 1.1970 g) with a yield of 80.4%.

[0075] 1 H NMR (300MHz, CDCl 3 )δ (ppm): 7.83 (d, J = 7.2Hz, 4H), 7.42-7.31 (m, 4H), 7.26-7.16 (m, 4H), 7.04 (d, J = 7.5Hz, 2H), 6.59 ( d,J=8.1Hz,2H).

[0076] Synthesis of Compound 13: Intermediate 12 (745.9mg, 2.0mmol), 3,6-dibromo-1,2-phenylenediamine (638.2mg, 2.4mmol) and p-toluenesulfonic acid (29.5mg, 8mol%) Add it to a 100 mL two-neck flask, add chloroform (20 mL) under a nitrogen atmosphere, and reflux the reaction overnight. After ...

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Abstract

The invention discloses a triphenylamine organic dye and a synthesis method thereof. The chemical structure of the triphenylamine organic dye is as shown in a general formula (1). In the formula (1),R<1> is selected from hydrogen or styryl, R<2> is selected from hydrogen or styryl, and the following structure is a quinoxaline derivative. The triphenylamine organic dye provided by the invention has a long conjugated D-pi-A structure, and meanwhile, molecules contain cyano groups and carboxyl, and the electrondrawing group is cyanoacetic acid. The triphenylamine organic dye can be used as a solar cell sensitizer, and has a good application prospect in dye-sensitized solar cells.

Description

technical field [0001] The invention belongs to the technical field of dye-sensitized solar cell sensitizers, and relates to a triphenylamine-based organic dye and a synthesis method thereof, in particular to a triphenylamine (TPA) structural unit based on a conjugated π-bridge, double Bond and D-A-π-A introduce organic dyes with electron-donating groups such as phenyl or quinoxaline units and their synthesis methods. Background technique [0002] As the most widely sourced green energy, solar energy is expected to alleviate the shortage of existing traditional energy resources and especially the greenhouse effect caused by increasing the utilization rate of solar energy. The sun produces 3.8×10 per hour 23 kWh of energy, of which 1.7 x 10 per day 5 TW of solar energy reaches the earth, and one-third is reflected back to space, which means that the solar energy received by the earth's surface per hour is much more than the energy used by human beings in a year. As the mos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04H01G9/20
CPCC09B23/04H01G9/2059Y02E10/542
Inventor 方敬坤李珂许梦晨赵思雨
Owner NANJING UNIV OF SCI & TECH
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