Thiazole triphenylamine photosensitive dye and preparation method thereof

A photosensitive dye, triphenylamine technology, applied in the field of organic dyes, can solve the problems of destroying the coplanarity of molecules, unfavorable electron transfer, narrowing the spectral absorption range of photosensitive dye molecules, etc., and achieves low preparation cost, improved electron donating ability, widened The effect of spectral absorption range

Inactive Publication Date: 2016-01-06
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Thiazole triphenylamine photosensitive dye and preparation method thereof
  • Thiazole triphenylamine photosensitive dye and preparation method thereof
  • Thiazole triphenylamine photosensitive dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Taking the preparation of thiazolone triphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0043]

[0044] 1, preparation formula 1 compound

[0045] Add 300mL toluene and 300mL distilled water to the three-neck round bottom flask, then add 45.3g (0.3mol) benzothiazolone, 54.0g (0.33mol) bromohexane, 13.2g (0.33mol) sodium hydroxide, 9.6g (0.03 mol) tetrabutylammonium bromide, reacted at 60°C for 8 hours, lowered to room temperature, separated, the organic phase was washed with distilled water until neutral, dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated, and the residue was subjected to column chromatography Separation (the eluent is a mixture of petroleum ether: ethyl acetate = 2:1), 64.8 g of the compound of formula 1 was obtained, with a yield of 92%. Its chemical reaction equation is as follows:

[0046]

[0047] 2. Preparation of the compound of fo...

Embodiment 2

[0067] Taking the preparation of thiazolone triphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0068]

[0069] 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 the corresponding examples to prepare thiazolone Triphenylamine photosensitive dye.

[0070] According to the method of Example 1, the thiazolone triphenylamine photosensitizing dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 5.96% and the short-circuit current was 12.9mA / cm after testing. 2 , the open circuit voltage is 690mV, and the fill factor is 0.67 (see figure 1 Middle curve 2), its photoelectric conversion efficiency reaches 84% ​​of the photoelectric conversion efficiency of N7...

Embodiment 3

[0072] Taking the preparation of thiazolone triphenylamine photosensitizing dyes with the following structural formula as an example, the preparation method is as follows:

[0073]

[0074] In the step 1 of the preparation of the compound of formula 1 in Example 1, the hexyl bromide used is replaced with equimolar decane bromide, and the other steps of this step are the same as in Example 1, and the other steps are the same as in the corresponding examples to prepare thiazole Ketotriphenylamine photosensitive dye.

[0075] According to the method of Example 1, the thiazolone triphenylamine photosensitizing dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 5.85% and the short-circuit current was 12.0mA / cm after testing. 2 , the open circuit voltage is 739mV, and the fill factor is 0.66 (see figure 1 Middle curve 3), its photoelectric conversion efficiency reaches 82% of the photoelectric conversion efficiency ...

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PUM

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Abstract

The invention discloses thiazole triphenylamine photosensitive dye and a preparation method thereof. The structural formula of the photosensitive dye can be found in the specification, wherein R1 stands for C1-C10 alkyl or C2-C10 alkenyl; Ar stands for a bridge chain constituted by aryl, heterocyclic ring aryl and the like. According to the thiazole triphenylamine photosensitive dye and the preparation method thereof, thiazolone containing electron-rich heteroatoms such as nitrogen, oxygen and sulfur is introduced into a triphenylamine electron donor, electron donating capability of the donor can be improved, the spectral absorption range of the photosensitive dye can be broadened more effectively, and the photosensitive dye can be used for preparing solar cells, contains no precious metal ruthenium, is low in preparation cost and simple in purification method and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and specifically relates to an organic dye in which thiazolone triphenylamine is an electron donor, aromatic hydrocarbons or heterocyclic aromatic hydrocarbons and derivatives thereof are bridge chains and are connected with electron-withdrawing groups. 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, electrolyt...

Claims

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Application Information

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IPC IPC(8): C09B23/04C09B23/14C07D277/68C07D417/14H01G9/20
Inventor 靳玲侠
Owner SHAANXI UNIV OF TECH
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