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Photosensitive dye with d-d-π-a structure using triphenylamine as a double electron donor and its preparation method and application

A technology of electron donor and photosensitive dye, which is applied in the field of solar cells to achieve the effect of low preparation cost, high photoelectric conversion efficiency and less process

Active Publication Date: 2019-10-25
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are relatively few studies and reports on the electron donor of organic dyes with D-D-π-A structure, and there is no dye structure design using triphenylamine as a double electron donor. The research carried out by the photosensitizing dye of the D-D-π-A structure has a large research space

Method used

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  • Photosensitive dye with d-d-π-a structure using triphenylamine as a double electron donor and its preparation method and application
  • Photosensitive dye with d-d-π-a structure using triphenylamine as a double electron donor and its preparation method and application
  • Photosensitive dye with d-d-π-a structure using triphenylamine as a double electron donor and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1 Photosensitizing dye I (2-cyano-3-((2-(4-(2-(4-methoxytriphenylamine))vinyl)triphenylamine) 3,4-ethylenedioxythiophene) Acrylic acid) and preparation method thereof

[0071] Photosensitizing dye Ⅰ uses triphenylamine as a double electron donor, EDOT as a π-conjugated bridge, and cyanoacetic acid as an electron acceptor. Its chemical structural formula is: Its synthetic route is as follows:

[0072]

[0073] The preparation method of photosensitizing dye I comprises the following steps carried out in sequence:

[0074] (1) Synthesis of Intermediate 1

[0075] Add 6g of 3,4-ethylenedioxythiophene and 150mL of anhydrous tetrahydrofuran into a 500mL four-necked reaction flask, protect with nitrogen, cool to -78°C, and stir for 30min. Slowly add 20 mL of 1.6M n-butyllithium hexane solution to the reaction flask dropwise using a syringe, and stir under this condition for 1 h after the dropwise addition is complete. A solution of tributyltin chloride in tetra...

Embodiment 2

[0106] Example 2 Photosensitizing dye II (2-cyano-3-((2-(4-(2-(4-n-hexyloxytriphenylamine))vinyl)triphenylamine) 3,4-ethylenedioxythiophene) Acrylic acid) and preparation method thereof

[0107] The chemical structural formula of photosensitizing dye II is:

[0108] The synthetic route of photosensitive dye II is as follows:

[0109]

[0110] The preparation method of photosensitizing dye II is similar to that of Example 1, except that the secondary electron donor in Example 1 is Intermediate 5, and this Example is Intermediate 11; correspondingly, the intermediate in Example 1 In this embodiment, bodies 6-8 are replaced by intermediate body 12, intermediate body 13, and intermediate body 14, respectively.

[0111] Intermediate 11 was prepared from 4-hexyloxytriphenylamine via Vilsmeier reaction, sodium borohydride reduction and Michaelis–Arbuzov reaction.

[0112] The synthetic method of intermediate 11 is carried out in the order of following steps (21)-(23):

[011...

Embodiment 3

[0131] Example 3 Photosensitizing dye III (2-cyano-3-((2-(4-(4-(4-methoxytriphenylamine))butadienyl)triphenylamine)3,4-ethylenedioxy Thiophene) acrylic acid) and preparation method thereof

[0132] Photosensitizing dye III is a D-D-π-A structure with triphenylamine as a double electron donor, and its chemical structural formula is:

[0133] The synthetic route of photosensitive dye III is as follows:

[0134]

[0135] The preparation method of photosensitizing dye III is similar to Example 1, the difference is that in Example 1, the primary electron donor is Intermediate 2, and the secondary electron donor is Intermediate 5. In this example, the primary electron donor is Intermediate 5. The donor is intermediate 16, and the secondary electron donor is intermediate 18 instead. Correspondingly, the intermediates produced in the subsequent reaction in this embodiment are intermediate 19, intermediate 20, and intermediate 21.

[0136] The synthesis of the primary electron d...

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Abstract

The invention discloses a photosensitive dye of a D-D-pi-A structure with triphenylamine as a two-electron donor as well as a preparation method and application of the photosensitive dye. According to the photosensitive dye, triphenylamine is adopted as the two-electron donor, 3,4-ethylene dioxythiophene is adopted as a pi conjugate bridge and cyanoacetic acid is adopted as an electron donor, the chemical structural formula of the photosensitive dye is as shown in the specification, and in the formula, R1 is a group of vinyl, butadienyl or p-divinyl benzene, and R2 is methoxy or hexyloxy. The photosensitive dye disclosed by the invention is diverse in structure and is capable of improving the dyeing property, and thus relatively high photoelectric conversion efficiency is achieved. The invention further provides a corresponding preparation method of the photosensitive dye. The photosensitive dye is prepared from a primary electron donor and a secondary electron donor of different structures through reaction. The preparation method is simple in process, low in preparation cost and environmental-friendly. The invention further provides corresponding application of the photosensitive dye. The photosensitive dye can be used for preparing dye-sensitized solar cells, and tests show about 6% of photoelectric conversion efficiency is achieved.

Description

technical field [0001] The invention belongs to the field of solar cells and relates to a photosensitive dye, in particular to a photosensitive dye with a D-D-π-A structure using triphenylamine as a double electron donor, a preparation method and application thereof. Background technique [0002] With the rapid development of society, energy structure problems and environmental pollution and destruction have become serious problems to be solved urgently in today's society. As a global issue of sustainable development, seeking and utilizing an economical renewable energy has become the consensus of all countries in the world. As an inexhaustible and inexhaustible clean energy, the development and utilization of solar energy is of Sex is becoming more prominent. [0003] Dye-sensitized solar cells (DSSC) is an important research direction of solar cells. Since it was invented by Swiss scientist Professor Gratzel in 1991 (Nature, 1991, 353, 737), due to its simple preparation ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C09B57/00H01G9/20
CPCC07D495/04C09B57/008H01G9/2059Y02E10/542
Inventor 吕海军周浩然靳根根于奕峰马伟情康彩红王丽丽
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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