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

A kind of bithiourea triphenylamine, photosensitive dye technology, applied in the field of organic dyes

Active Publication Date: 2021-06-15
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'-di(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof
  • 4,4'-di(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof
  • 4,4'-di(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation method of the preparation of the 4,4'-di (alkylphenylphenyl) joint thiophene bridge, the preparation formula is prepared as follows.

[0040]

[0041] 1, preparation formula 1 compound

[0042] 100 ml of tetrahydrofuran and 20 mL of water were added to the three round bottom flask, and then 6.52 g (0.04 mol) 3-bromothiophene, 8.54 g (0.048 mol) of butylbenzonic acid, 2.31 g (0.002 mol) four (triphenylphosphine) Palladium, 11.04 g (0.08 mol) potassium carbonate, 70 ° C for 10 hours, dried to room temperature, dispense, dry, filtered, evaporated, evaporated, residue (elution) with anhydrous magnesium sulfate The agent is petroleum ether) to give 7.44 g of the compound of formula 1, yield 86%. Its chemical reaction equation is as follows:

[0043]

[0044] 2, prepare formula 2 compound

[0045] 100 ml of tetrahydrofuran was added to the three round bottom flask, and 5.2 g (0.024 mol) formula 1 compound, 3.35 g (0.029 mol) N, N, N, N-tetramethylenediamine (T...

Embodiment 2

[0064] The preparation method of the preparation of the 4,4'-di (alkylphenylphenyl) joint thiophene bridge, the preparation formula is prepared as follows.

[0065]

[0066] In the preparation of the formula 1 of Example 1, the other step of methylbenzezene boric acid is used in the preparation formula 1 of Example 1. The other steps of this step are the same as that of the first embodiment, and the other steps are the same as the corresponding embodiment. The preparation of 4,4'-di (alkylphenyl) coupling bridging thiourea pyremine photosensitive dye is prepared.

[0067] According to the method of Example 1, the 4,4'-bis (alkylphenyl) joint of the present embodiment was prepared into a dye-sensitized solar cell, and the photoelectric conversion efficiency of the test was 7.97%. Short-circuit current is 16.6mA / cm 2 The open circuit voltage is 774mV, and the filling factor is 0.62. The photoelectric conversion efficiency is higher than the photoelectric conversion efficiency of...

Embodiment 3

[0069] The preparation method of the preparation of the 4,4'-di (alkylphenylphenyl) joint thiophene bridge, the preparation formula is prepared as follows.

[0070]

[0071] In the preparation of the formula 1 of Example 1, the other step of ketzhenobhenic acid used to be used in the preparation formula 1 of Example 1 was the same as that of the first embodiment, and the other steps were the same as the corresponding embodiment. The preparation of 4,4'-di (alkylphenyl) coupling bridging thiourea pyremine photosensitive dye is prepared.

[0072] According to the method of Example 1, the 4,4'-di (alkylphenyl) joint of the present embodiment was prepared into a dye-sensitized solar cell in a dye-sensitized solar cell, and the photoelectric conversion efficiency of the test was 8.00%. Short-circuit current is 16.2mA / cm 2 The open circuit voltage is 796 mV, and the filling factor is 0.62. The photoelectric conversion efficiency is higher than the photoelectric conversion efficiency...

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Abstract

The invention discloses a 4,4'-bis(alkylbenzene)bithiophene bridged thiourea triphenylamine photosensitive dye and a preparation method thereof. The structural formula of the photosensitive dye is as follows: in the formula, R 1 stands for C 1 ~C 10 Alkyl; D is the electron donor of thiourea triphenylamine. The present invention introduces alkylbenzene at the 4 and 4' positions of the bithiophene bridge chain, which can achieve the dual effects of broadening the absorption band range of pure organic photosensitive dyes and inhibiting intermolecular agglomeration: on the one hand, alkylbenzene can further improve the bithiophene bridge. The electron-rich property of the thiophene bridge chain is conducive to the transfer of electrons from the donor to the acceptor, thereby broadening the absorption band range of the dye; on the other hand, the alkylbenzene has a certain steric hindrance, which can effectively inhibit the agglomeration of the dye molecules . 4,4'-bis(alkylbenzene)bithiophene-bridged thiourea triphenylamine photosensitizing dye can be used to prepare solar cells. Because it does not contain noble metal ruthenium, the preparation cost is low, and the purification method is simple, it has broad application prospects.

Description

Technical field [0001] The present invention belongs to the technical field of organic dyes, and in particular, the organic dye of a bridge chain is attached to a 4,4'-di (alkylphenyl) group with thiophene, a bridge chain, and a silicate group. Background technique [0002] Energy Crisis and Environmental Pollution The challenges proposed by the global sustainable development are increasingly intensified, and the development of clean-renewable new energy has become a major direction in the world's planning. Compared with petrochemical fuel, nuclear energy, water energy, wind energy, etc., solar energy has a unique advantage, due to its total amount, safe and not limited by geographical conditions. Since 1954, the US Bel laboratory has successfully developed the first practical silicon solar cell and used for artificial satellite power supply, solar cell research has achieved great progress, and has now been developed to the third generation solar cell. Among them, the manufacturi...

Claims

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Application Information

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Patent Type & Authority Patents(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