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Carbazole-thiophene compound for dye-sensitized solar cell material, and preparation method thereof

A technology for solar cells and dye sensitization, which is applied in the field of carbazole-thiophene compounds and their preparation, can solve the problems of toxic and expensive, and achieve the effects of simple and convenient post-processing, high yield and mild reaction conditions

Inactive Publication Date: 2014-12-17
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Organic photosensitive dye metal complexes have very high chemical stability, but these metals are mostly rare metals, toxic and expensive

Method used

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  • Carbazole-thiophene compound for dye-sensitized solar cell material, and preparation method thereof
  • Carbazole-thiophene compound for dye-sensitized solar cell material, and preparation method thereof
  • Carbazole-thiophene compound for dye-sensitized solar cell material, and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the synthesis of dyestuff 3-(4-cyanoacrylate thiophene)-N-n-hexylcarbazole

[0037] (1) Synthesis of N-hexylcarbazole

[0038] Weigh 1.65 g (10 mmol) of carbazole into a round bottom flask equipped with a stirring bar, add 10 mL of anhydrous DMF to dissolve completely at room temperature, then add 0.4 g NaH to the flask, seal with oil, stir at room temperature for 20 min, and use a constant pressure funnel to Add 2 mL of n-C solution dropwise 6 h13 Br in DMF solution 3mL, 80 ℃ oil bath reflux 3h. After cooling to room temperature, pour it into water and stir thoroughly, a beige solid is formed, stand until the solution becomes clear, filter with suction, recrystallize with ethanol to obtain white needle crystals, filter with suction, and air-dry to obtain 1.48g of needle crystal products, Yield 58.85%. 1H-NMR (CDCl 3 ,400Hz):δ(ppm):8.09(d,J=7.6Hz,2H),7.38~7.48(m,4H),7.21(d,J=8.0Hz,2H),4.28(t,2H),1.86 (m,2H), 1.33(m,6H), 0.86(t,3H). FT-IR (KBr, cm -1...

Embodiment 2

[0045] Embodiment 2: The ultraviolet absorption spectrum of 3-(4-cyanoacrylic acid thiophene)-N-n-hexylcarbazole and the measurement of fluorescence spectrum

[0046] The ultraviolet-visible absorption spectrum was measured on a Shimadzu UV-3600 ultraviolet-visible spectrophotometer, and the measurement range was between 200-1000nm. The concentration of the sample to be tested is 1.0×10 -5 mol / L test solution. The ultraviolet-visible spectrum and fluorescence spectrum were measured respectively. From figure 1 Visible dyes have two absorption peaks: the absorption peak at 291nm in the high energy region is the carbazole functional group π-π * The characteristic absorption peak, the position of the absorption peak in the low energy region is located at 426nm, which is attributed to the intramolecular charge transfer (ICT) transition of the whole molecule. From the analysis of the ultraviolet-visible absorption spectrum, the electron-withdrawing group of the dye is cyanoaceti...

Embodiment 3

[0048] Embodiment 3: the mensuration of the electrochemical voltammetry characteristic of 3-(4-cyanoacrylic acid thiophene)-N-n-hexylcarbazole

[0049] The redox energy level of the dye in the solution was determined by cyclic voltammetry on Chenhua CHI660 instrument electrochemical workstation. The test uses a three-electrode working system: the working electrode is a glassy carbon electrode, the counter electrode is a Pt wire electrode, and the reference electrode is a saturated calomel electrode. The solvent used in the test was chromatographically pure acetonitrile. The electrolyte was 0.05M tetrabutylammonium perchlorate. In order to reduce the error, each sample was scanned 3 times.

[0050] The reference electrode used in the experiment is a saturated calomel electrode, and its potential needs to be converted into a standard hydrogen electrode potential, which is 0.24 eV relative to the NHE potential, HOMO=eE ox +0.24. image 3 is the cyclic voltammetry characterist...

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Abstract

The invention discloses a carbazole-thiophene compound for a dye-sensitized solar cell material, and a preparation method thereof. The compound is a carbazolyl-thienyl group-containing dye-sensitized solar cell material obtained through a Knoevenagel condensation reaction of carbazole-thiophene-based aldehyde and cyanoacetic acid, and the molecule of the compound is characterized in that the structure of the compound contains an N-substituted carbazolyl group, a thienyl group, a cyan group and a carboxyl group; and the compound has a long conjugate D-pi-A structure, and contains the cyan group and the carboxyl group, an electron-withdrawing group is cyanoacetic acid, the introduction of the thienyl group increases the conjugate bridge length of the dye molecule, so the compound is an ideal solar cell sensitizer. The carbazole-thiophene compound has the advantages of simple synthesis route, mild reaction conditions, simple and convenient post-treatment, high yield, and convenience for application.

Description

technical field [0001] The invention relates to a material for dye-sensitized solar cells, in particular to a carbazole-thiophene compound used for dye-sensitized solar cells and a preparation method thereof. Background technique [0002] With the development of social science and technology, the current situation of energy shortage is becoming more and more obvious, so people are actively exploring solar energy, a green and resource-rich energy source, to solve the problem of energy depletion. A solar cell is a device that converts solar energy into electrical energy. In the past few decades, solar cells have been developed rapidly. Among them, the research on inorganic solar cells is the most mature, and the degree of marketization is the highest. Inorganic solar cells mainly use semiconductors such as crystalline silicon and inorganic compounds as photosensitive materials, and their excellent performance occupies an irreplaceable position in high-tech fields such as avia...

Claims

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Application Information

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IPC IPC(8): C07D409/04C09B57/00H01G9/20
CPCC07D409/04C09B23/04H01G9/2059Y02E10/542Y02P70/50
Inventor 李村朱维菊张晴方敏
Owner ANHUI UNIVERSITY
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