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Organic dye and preparation method and application thereof

An organic dye, selected technology, applied in the direction of organic dyes, organic chemistry, azo dyes, etc., can solve the problems of insufficient spectral response range, cumbersome preparation process, high cost, etc., and achieve easy preparation and high product yield And the effect of high purity and high degree of commercialization of raw materials

Inactive Publication Date: 2010-09-22
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the preparation process of ruthenium series dyes is cumbersome, the spectral response range is not wide enough, and ruthenium is a noble metal, the cost is high, so people actively develop pure organic dyes
However, the sensitization of a single organic dye is limited by the absorption spectrum of the dye, and it is difficult to match the emission spectrum of the sun. Therefore, people have designed dyes with different structures to use together to make up for the shortcomings of their respective absorption spectra. Effect

Method used

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  • Organic dye and preparation method and application thereof
  • Organic dye and preparation method and application thereof
  • Organic dye and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1 organic dye (Ⅰ-1)

[0030]

[0031] Step 1 In a four-necked flask equipped with a stirrer, use 130 ml of hydrogen bromide glacial acetic acid solution to heat up to 30-40°C to dissolve 0.02 mole of 4-dianilinoaniline, and then add 1.4 grams of it in batches at a temperature of 0-8°C Sodium nitrite reacts with diazonium. After 1 hour, the diazonium solution was poured into the glacial acetic acid solution of salicylaldehyde to carry out the azo reaction. The azo reaction product system was poured into 100 ml of water, and the precipitate was collected. The filter cake was recrystallized with N,N-dimethylformamide / ethanol (volume ratio=1:1), and dried in vacuo to obtain 6.2 grams of yellow powder 5-(4-dianilinophenylazo)salicylaldehyde , yield 79%. The melting point is 166-167°C.

[0032] h 1-NMR (DMSO-d 6 , δ): 5.32 (1H), 6.65-8.18 (m, 17H), 10.03 (s, 1H).

[0033] Elemental Analysis: C 25 h 19 N 3 o 2 Found (calculated): C76...

Embodiment 2

[0043] The preparation of embodiment 2 organic dyes (I-2)

[0044]

[0045] According to the preparation method and steps of Example 1, the 4-dianilinoaniline in Step 1 of the Example was replaced with aniline to prepare a bright orange-red organic dye (I-2), with a melting point of 237-239°C.

[0046] The characteristic UV-visible light absorption peak λmax=474nm and the characteristic fluorescence emission spectrum peak λmax=547nm of the organic dye (I-2) in N,N-dimethylformamide solution.

Embodiment 3

[0047] The preparation of embodiment 3 organic dyes (I-3)

[0048]

[0049] According to the preparation method and steps of Example 1, the 4-dianilinoaniline in step 1 in the example was replaced with 4-dimethylaminoaniline to prepare bright maroon organic dye (I-3), with a melting point of 251-252°C .

[0050] Organic dye (I-3) has UV-visible light absorption characteristic peak λmax=551nm and fluorescence emission spectrum characteristic peak λmax=634nm in N,N-dimethylformamide solution.

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Abstract

The invention relates to an organic dye, in particular to a D-N=N-pi-A organic dye, wherein D refers to an electron repulsive structure unit, N=N refers to an azo structure unit, pi refers to a coumarin conjugate structure unit, and A refers to a rhodanine electron acceptor structure unit. The invention aims to find a functional organic dye which has the advantages of high molecular tailoring properties, wide spectral response range, low synthesis cost and capacity of absorbing most visible light and can be applied to the fields such as acid dyes, fluorescent dyes, organic electroluminescent materials and dye-sensitized nano TiO2 solar cells.

Description

technical field [0001] The invention relates to an organic dye, in particular to an organic dye composed of an electron-pushing group-azo-coumarin-rhodenine structural unit. It belongs to the field of fine chemicals. technical background [0002] In the past two decades, dye-sensitized nano-TiO 2 The research, application and commercial development of solar cells (dye-sensitized solar cells, DSSCs) as a new energy source have become the focus of the world's developed countries. Compared with monocrystalline silicon or polycrystalline silicon solar cells, this type of solar cell has the characteristics of a wide range of production raw materials and low manufacturing process costs. The role of organic dyes used on DSSCs is to absorb sunlight. Organic dye molecules absorb photons and are excited to change from the ground state to the excited state to generate electrons and holes, and the electrons and holes are transferred to nano-TiO. 2 in the conduction band of the semico...

Claims

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Application Information

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IPC IPC(8): C09B29/12H01G9/20H01M14/00H01L51/42H01L51/48C07D417/06
CPCY02E10/542Y02E10/549C09K11/06C09B56/16H01G9/2059C09K2211/1022C09K2211/1037H10K85/652
Inventor 张田林万伟清施莉莉李赞周琴琴丁志丹
Owner HUAIHAI INST OF TECH
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