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4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof

A technology of bisthiourea triphenylamine and photosensitizing dyes, which is applied in the field of organic dyes to achieve the effects of high open circuit voltage, broadening the absorption band range and high photoelectric conversion efficiency

Active Publication Date: 2019-04-05
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the shortcomings of the above-mentioned organic photosensitive dyes, to provide a 4,4'-di(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye with a wide absorption band range and not easy to agglomerate, And provide a kind of simple operation, high yield preparation method for this dye

Method used

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  • 4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof
  • 4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof
  • 4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof

Examples

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Effect test

Embodiment 1

[0039] Taking the preparation of the following 4,4'-di(alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye as an example, the preparation method is as follows:

[0040]

[0041] 1, preparation formula 1 compound

[0042] Add 100mL tetrahydrofuran and 20mL water to a three-neck round bottom flask, then add 6.52g (0.04mol) 3-bromothiophene, 8.54g (0.048mol) p-butylphenylboronic acid, 2.31g (0.002mol) tetrakis (triphenylphosphine) ) palladium, 11.04g (0.08mol) potassium carbonate, 70 ℃ of reaction 10 hours, down to room temperature, liquid separation, the organic phase is dried with anhydrous magnesium sulfate, filters, evaporates solvent, and the residue is separated by column chromatography (elution The agent is petroleum ether) to obtain 7.44 g of the compound of formula 1, with a yield of 86%. Its chemical reaction equation is as follows:

[0043]

[0044] 2. Preparation of the compound of formula 2

[0045] Add 100mL tetrahydrofuran to a thr...

Embodiment 2

[0064] Taking the preparation of the following 4,4'-di(alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye as an example, the preparation method is as follows:

[0065]

[0066] In step 1 of the compound of formula 1 prepared in Example 1, the p-butylphenylboronic acid used is replaced with equimolar p-tolueneboronic acid, 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 , prepared as 4,4'-bis(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitizing dye.

[0067] According to the method of Example 1, the 4,4'-di(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 7.97%, The short circuit current is 16.6mA / cm 2 , The open circuit voltage is 774mV, and the fill factor is 0.62. Its photoelectric conversion efficiency is higher...

Embodiment 3

[0069] Taking the preparation of the following 4,4'-di(alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye as an example, the preparation method is as follows:

[0070]

[0071] In the preparation formula 1 compound step 1 of embodiment 1, p-butylphenylboronic acid used is replaced with equimolar p-quinylphenylboronic acid, other steps of this step are identical with embodiment 1, and other steps are identical with corresponding embodiment , prepared as 4,4'-bis(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitizing dye.

[0072] According to the method of Example 1, the 4,4'-bis(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 8.00%, 8.00%, The short circuit current is 16.2mA / cm 2 , The open circuit voltage is 796mV, and the fill factor is 0.62. Its photoelectric conversion efficiency is high...

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Abstract

The invention discloses a 4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and a preparation method thereof. A structural formula of the photosensitive dye is asshown in the specification, wherein R1 represents C1-C10 alkyl; and D is a thiourea triphenylamine electron donor. Alkylbenzene is introduced at the 4 and 4' positions of the bithiophene bridge chain,so that the double effects of widening the absorption band range of pure organic photosensitive dye and inhibiting intermolecular agglomeration can be achieved: on the one hand, the alkylbenzene canfurther improve the electron-rich property of the bithiophene bridge chain, and is beneficial to electron transfer from a donor to a receptor, so as to widen the absorption band range of the dye; on the other hand, the alkylbenzene has certain steric hindrance, which can effectively inhibit the aggregation of dye molecules. The 4,4'-bis (alkylbenzene) bithiophene bridged thiourea triphenylamine photosensitive dye can be used for preparing solar cells, as the dye does not contain noble metal ruthenium, the preparation cost is low, and the purification method is simple, so that the dye has wideapplication prospect.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to an organic dye using thiourea triphenylamine as an electron donor and 4,4'-di(alkylbenzene)bithiophene as a bridging chain connected with an electron-withdrawing group. Background technique [0002] The energy crisis and environmental pollution pose increasing challenges to global sustainable development, and the development of clean and renewable new energy has become a major direction in the planning of countries around the world. Compared with fossil fuels, nuclear energy, water energy, wind energy, etc., solar energy has unique advantages because of its large amount, safety, and is not restricted by geographical conditions. Since Bell Laboratories in the United States successfully developed the first practical silicon solar cell and used it for artificial satellite power in 1954, solar cell research has made great progress, and has now developed to the third ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C09B57/00H01G9/20H01G9/042
CPCC07D409/14C09B57/00H01G9/20H01G9/2022H01G9/2059Y02E10/542
Inventor 伍致生郭旺军张杰宋新潮刘亚东王户生周继华
Owner XIAN MODERN CHEM RES INST