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Indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, synthetic method and application thereof

A kind of arylmethylene malononitrile, synthesis method technology, applied in the direction of methine-based/polymethine-based dyes, chemical instruments and methods, organic dyes, etc., can solve the problems of high production cost, high purification difficulty, long synthesis route and the like

Active Publication Date: 2015-11-11
XUZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to overcome the shortcomings of existing co-sensitizing dyes, such as high production cost, long and complicated synthetic route, and high difficulty in purification, the present invention provides an indole-triphenylamine-arylenemalononitrile solar co-sensitizing dye and its Synthesis method and use

Method used

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  • Indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, synthetic method and application thereof
  • Indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, synthetic method and application thereof
  • Indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, synthetic method and application thereof

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Embodiment

[0080] 1. Synthesis of indole-triphenylamine-arylenemalononitrile red light materials: the synthesis route is as follows:

[0081]

[0082] The structural formula of the product is:

[0083]

[0084] 1) Synthesis of compound 2:

[0085]

[0086] Add 4.0g of triphenylamine and 17.8mL of DMF to the single-necked flask, stir to dissolve, slowly add 7.6mL of phosphorus oxychloride in an ice bath, continue stirring for half an hour under ice bath, and after stirring for 1 hour at room temperature, then slowly warm up to 45℃ for reaction 2h. After the reaction, pour the reaction solution into ice water, and neutralize the unreacted POCl with NaOH 3 , Stand and filter to obtain the initial product, recrystallize with ethanol to obtain a pale yellow solid, which is compound 2, the yield is 92%, and the melting point is 132-135°C. 1 HNMR(CDCl 3 , 400MHz, TMS): δ=9.79(s,1H), 7.69-7.71(d,J=8.9,2H), 7.35-7.39(t,J=7.8,4H), 7.18-7.21(m,6H), 7.03 (d, J=8.9, 2H).

[0087] 2) Synthesis of compound 3...

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Abstract

The invention discloses an indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, a synthetic method and application thereof. The synthetic method comprises the following steps: adopting triphenylamine as the raw material, carrying out reaction on triphenylamine and POCl3 in a DMF solvent to compound and obtain an intermediate 4-(diphenyl amido) benzaldehyde; carrying out reaction on the 4-(diphenyl amido) benzaldehyde to obtain 4-bis (4-iodophenyl) aminobenzaldehyde; respectively carrying out reaction on the 4-bis (4-iodophenyl) aminobenzaldehyde and indole, 2-methylindole and 3-methylindole to obtain an indole-triphenylamine aldehyde derivative; respectively carrying out reaction on the indole-triphenylamine aldehyde derivative and cyanoacetic acid, malononitrile or 2-(3, 5, 5-trimethyl cyclohexene-2-octenylidene) malononitrile to obtain an indole-arylmethylidenemalononitrile-triphenylamine derivative. According to the synthetic method, the relevant optical property, photo-electro transition rate and co-sensitization efficiency of the product are primarily studied, and the foundation for developing the dye into a novel solar energy co-sensitization dye with excellent properties is laid.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and particularly relates to an indole-triphenylamine-arylenemalononitrile solar energy co-sensitizing dye and its synthesis and application. Background technique [0002] The 21st century has become an era of energy competition. The continuous consumption of non-renewable energy by mankind has caused serious pollution to the environment while depleting its resources. This forces people to seek new energy sources to alleviate the energy crisis and reduce environmental pollution. [0003] Solar energy has become the most concerned research hotspot in the field of new energy due to its freedom from geographical restrictions, abundant reserves, and diversified utilization methods. [0004] Dye-sensitized solar cells have the advantages of simple manufacture, low cost, long service life (up to 15 years), and high photoelectric conversion rate (up to 7%), and become a new way to utilize solar energ...

Claims

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Application Information

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IPC IPC(8): C09B23/04C07D209/08H01G9/20H01G9/042
CPCY02E10/542Y02P70/50
Inventor 宛瑜张文莉刘振涛苑睿吴翚
Owner XUZHOU NORMAL UNIVERSITY
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