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

A technology of bisthiourea triphenylamine and photosensitizing dyes, applied in the field of organic dyes, can solve the problems of aggravating the intermolecular agglomeration of photosensitizing dyes, and achieve the effects of high photoelectric conversion efficiency, low preparation cost, and improvement of short-circuit current density

Active Publication Date: 2019-05-03
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The study found that extending the conjugated bridge chain can broaden the absorption band range of the photosensitizing dye, but simply extending the conjugated bridge chain will aggravate the agglomeration of the photosensitizing dye molecules to a certain extent

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Taking the preparation of 4,4'-bis(alkoxybenzene) bithiophene bridged thiourea triphenylamine photosensitizing dye as an example with the following structural formula, the preparation method is as follows:

[0038]

[0039] 1, preparation formula 1 compound

[0040] Add 100mL tetrahydrofuran and 20mL water to a three-neck round bottom flask, then add 6.52g (0.04mol) 3-bromothiophene, 7.97g (0.048mol) p-ethoxyphenylboronic acid, 2.31g (0.002mol) tetrakis (triphenyl Phosphine) palladium, 11.04g (0.08mol) potassium carbonate, reacted at 70°C for 10 hours, cooled to room temperature, separated liquids, dried the organic phase with anhydrous magnesium sulfate, filtered, evaporated the solvent, and the residue was separated by column chromatography (washing The removing agent is petroleum ether) to obtain 7.18 g of the compound of formula 1 with a yield of 88%. Its chemical reaction equation is as follows:

[0041]

[0042] 2. Preparation of the compound of formula 2 ...

Embodiment 2

[0063] Take the preparation of 4,4'-di(alkoxyphenyl) bithiophene bridged thiourea triphenylamine photosensitizing dye as an example with the following structure, the preparation method is as follows:

[0064]

[0065] In the preparation formula 1 compound step 1 of embodiment 1, p-ethoxyphenylboronic acid used is replaced with equimolar p-methoxyphenylboronic acid, other steps of this step are the same as in Example 1, and other steps are implemented with corresponding Example is the same, prepared as 4,4'-bis (alkoxyphenyl) bithiophene bridged thiourea triphenylamine photosensitive dye.

[0066] According to the method of Example 1, the 4,4'-bis(alkoxyphenyl)bithiophene bridged thiourea triphenylamine photosensitive dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 7.98% after testing , Short circuit current is 16.8mA / cm 2 , The open circuit voltage is 766mV, and the fill factor is 0.62. Its photoelectric c...

Embodiment 3

[0068] Take the preparation of 4,4'-di(alkoxyphenyl) bithiophene bridged thiourea triphenylamine photosensitizing dye as an example with the following structure, the preparation method is as follows:

[0069]

[0070] In the preparation formula 1 compound step 1 of embodiment 1, p-ethoxyphenylboronic acid used is replaced with equimolar p-quiloxyphenylboronic acid, and other steps of this step are the same as in Example 1, and other steps are carried out with corresponding Example is the same, prepared as 4,4'-bis (alkoxyphenyl) bithiophene bridged thiourea triphenylamine photosensitive dye.

[0071] According to the method of Example 1, the 4,4'-bis(alkoxyphenyl)bithiophene bridged thiourea triphenylamine photosensitive dye of this example was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency was 8.07% after testing , Short circuit current is 16.4mA / cm 2 , The open circuit voltage is 794mV, and the fill factor is 0.62. Its photoelectr...

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Abstract

The invention discloses a 4,4'-bis(alkoxybenzene)bithiophene bridged thioureido triphenylamine photosensitive dye and a preparation method thereof. The structural formula of the photosensitive dye isas follows, wherein R<1> represents alkyl of C<1>-C<10>, and D is a thioureido triphenylamine electron donor. According to the invention, alkoxybenzene is introduced to two positions of 4 and 4 'of abithiophene bridge chain, so that double effects of broadening the absorption spectrum band of a pure organic photosensitive dye and inhibiting intermolecular agglomeration can be achieved. On one hand, the alkoxybenzene can further improve electron-rich performance of the bithiophene bridge chain, and transfer of electrons from the donor to a receptor is facilitated, so that the absorption spectrum band range of the dye is widened; and on the other hand, the alkoxybenzene has certain steric hindrance, so that agglomeration of dye molecules can be effectively inhibited. The 4,4'-bis(alkoxybenzene)bithiophene bridged thioureido triphenylamine photosensitive dye can be used for preparing a solar cell. The dye does not contain noble metal ruthenium, so that preparation cost is low; the purification method is simple; and the application prospect is wide.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to an organic dye with thiourea triphenylamine as an electron donor and 4,4'-bis(alkoxybenzene)bithiophene as a bridging chain connected with an electron-withdrawing group. Background technique [0002] 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 generation of solar cells. Among them, dye-sensitized solar cells (DSSCs) are currently a research hotspot in the field of solar cells due to their simple manufacturing process, low cost, and high photoelectric conversion efficiency. The components of DSSCs include photoanode, photosensitizing dye, electrolyte and counter electrode, and photosensitizing dye is mainly responsible for capturing photons and sending TiO 2 The conductio...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20H01G9/042
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