A kind of thiazolethione triphenylamine photosensitive dye and preparation method thereof

A technology of photosensitive dyes and thiazolethiones, which is applied in the field of organic dyes, can solve the problems of destroying the coplanarity of molecules, narrowing the spectral absorption range of photosensitizing dye molecules, and unfavorable electron transfer, so as to achieve low preparation costs, improve electron donating ability, The effect of broadening the spectral absorption range

Inactive Publication Date: 2017-05-10
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the steric hindrance of the adjacent alkyl groups in the donor causes the plane distortion of the donor, which is not conducive to the transfer of electrons from the donor to the acceptor to a certain extent. In addition, this distortion destroys the coplanarity of the molecules to a certain extent. , so that the spectral absorption range of photosensitizing dye molecules is narrowed

Method used

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  • A kind of thiazolethione triphenylamine photosensitive dye and preparation method thereof
  • A kind of thiazolethione triphenylamine photosensitive dye and preparation method thereof
  • A kind of thiazolethione triphenylamine photosensitive dye and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Take the preparation of thiazolethioketotriphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0036]

[0037] 1, preparation formula 1 compound

[0038] Add 300mL toluene and 300mL distilled water to a three-neck round bottom flask, then add 50.1g (0.3mol) benzothiazolethione, 54.0g (0.33mol) bromohexane, 13.2g (0.33mol) sodium hydroxide, 9.6g ( 0.03mol) tetrabutylammonium bromide, react at 60°C for 12 hours, cool down to room temperature, separate liquids, wash the organic phase with distilled water until neutral, dry with anhydrous magnesium sulfate, filter, evaporate the solvent, and use the column layer Analysis and separation (eluent is the mixed solution of sherwood oil:ethyl acetate=2:1), obtains formula 1 compound 66.3g, and its yield is 88%, and chemical reaction equation is as follows:

[0039]

[0040] 2. Preparation of the compound of formula 2

[0041] Add 400mL of chlorofor...

Embodiment 2

[0061] Take the preparation of thiazolethioketotriphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0062]

[0063] In the step 1 of the preparation of the compound of formula 1 in Example 1, the hexyl bromide used is replaced with equimolar methyl iodide, the other steps of this step are the same as in Example 1, and the other steps are the same as in Example 1 to prepare thiazolethione The triphenylamine photosensitive dye has an ultraviolet absorption range of 300-612nm and a maximum absorption wavelength of 450nm.

[0064] According to the method of Example 1, the thiazolethioketotriphenylamine photosensitive dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 6.14% and the short-circuit current was 13.1mA / cm after testing. 2 , the open circuit voltage is 700mV, and the fill factor is 0.67 (see figure 1 Middle curve 2), its photoel...

Embodiment 3

[0066] Take the preparation of thiazolethioketotriphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0067]

[0068] In step 1 of the preparation of the compound of formula 1 in Example 1, the hexyl bromide used is replaced by equimolar decane bromide, the other steps of this step are the same as in Example 1, and the other steps are the same as in Example 1 to prepare thiazole sulfur Ketotriphenylamine photosensitive dye has an ultraviolet absorption range of 300-610nm and a maximum absorption wavelength of 445nm.

[0069] According to the method of Example 1, the thiazolethioketotriphenylamine photosensitizing dye of this example was prepared into a dye-sensitized solar cell. After testing, the photoelectric conversion efficiency was 6.14%, and the short-circuit current was 12.5mA / cm 2 , the open circuit voltage is 745mV, and the fill factor is 0.66 (see figure 1 Middle curve 3), its photoelectri...

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Abstract

The invention discloses a thiazolidinethione and triphenylamine light-sensitive dye and a preparation method thereof, and the structural formula of the light-sensitive dye is as follows, ( image file= minute DDA0000833408650000011. TIFminutewi= minute 869 minute he=minute 556 minute / ) wherein R1 in the formula represents C1 to C10 alkyl or C2 to C10 alkenyl. According to the thiazolidinethione and triphenylamine light-sensitive dye, thiazolidinethione containing rich electronic heteroatom such as nitrogen, sulphur and the like is introduced into a triphenylamine electron donor, so that the electron supplying capability of the donor can be increased, the spectral absorption range of the light-sensitive dye can be effectively widened, the thiazolidinethione and triphenylamine light-sensitive dye can be used for preparing solar cells, does not contain precious metal of ruthenium and has wide application prospects, the preparation cost is low, and a purification method is simple.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and specifically relates to an organic dye with thiazolethioketotriphenylamine as an electron donor, benzene as a bridging chain connected with an electron-withdrawing group, and a preparation method of the dye. Background technique [0002] With the increasing human demand for energy and the emergence of environmental problems such as the greenhouse effect, the development of new renewable energy has received great attention from governments. Due to the low manufacturing cost, high photoelectric conversion efficiency and simple process of dye-sensitized solar cells, such cells are a focus of laboratory basic research and industrial application development. [0003] Generally, dye-sensitized solar cells are composed of conductive substrate materials (transparent conductive electrodes), nanoporous semiconductor films, photosensitizing dyes, electrolytes, and counter electrodes. Among them, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/04C09K11/06H01G9/042H01G9/20
Inventor 靳玲侠
Owner SHAANXI UNIV OF TECH
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