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2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran

A technology of nitrophenylazo and o-hydroxybenzaldehyde is applied in the field of novel organic semiconductor electron acceptor compounds and their preparation, and can solve the problem of shortening the exciton diffusion distance, increasing the contact area between the electron donor TBP and the electron acceptor, The problems of increasing short-circuit current of photovoltaic cells, etc., can reduce the synthesis cost, shorten the diffusion distance, and reduce the production cost.

Active Publication Date: 2021-11-12
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Accordingly, increasing the contact area between the electron donor TBP and the electron acceptor and shortening the diffusion distance of the excitons can lead to an increase in the short-circuit current of the photovoltaic cell.

Method used

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  • 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran
  • 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran
  • 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] In a three-necked flask, add 4-nitroaniline (10mmol), add 10mL of dilute hydrochloric acid solution (4mol / L), heat to make it completely dissolved, cool in an ice bath, add an aqueous solution of sodium nitrite (0.76g, 11mmol) , after keeping it at 2°C for 3 hours, add an appropriate amount of urea to remove unreacted sodium nitrite to make a diazonium salt; take another 500ml four-necked bottle, dissolve 0.61g (5mmol) of o-hydroxybenzaldehyde in 50mL of ethanol, and then add 0.2g sodium bicarbonate and 2.12g sodium carbonate, add the previously prepared diazonium salt into o-hydroxybenzaldehyde solution, continue to react for 4h after adding, add dilute hydrochloric acid solution to remove all sodium carbonate and sodium bicarbonate, add 200mL of water, then magnetically stirred, heated to 80°C and kept for 1 h, cooled, filtered, and dried to obtain the product: 2-hydroxy-5-(4-nitrophenylazo)benzaldehyde. The weighed weight was 1.28g, and the yield was 94.6%.

[0039]...

Embodiment 2-13

[0041] On the basis of Example 1, adjust the amount of reaction raw materials and reaction conditions, as shown in the following table.

[0042]

[0043]

[0044] Step 2: Preparation Example of 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran.

Embodiment 15

[0046] In a 250mL three-necked flask, dissolve 2-hydroxy-5-(4-nitrophenylazo)benzaldehyde (2.0mmol) and p-nitrophenylacetonitrile (2mmol) in 20mL absolute ethanol, and blow nitrogen Protection, after heating and stirring to reflux, add piperazine (0.1mmol), continue to reflux for 6 hours, cool to room temperature, crystals are precipitated, washed with saturated ammonium chloride solution, washed with a small amount of water, and dried to obtain reddish-brown crystals 0.77g. Yield: 92.8%.

[0047] 1 H NMR (400MHz, DMSO-D 6 ,25°C, TMS): δ(ppm)=7.00(1H,d,J=6.9Hz,Ar-H),7.46(1H,d,J=7.8Hz,Ar-H),7.85(1H,d, J=8.0Hz, Ar-H), 7.91(2H,d, J=6.8Hz, Ar-H), 8.04(4H,m, J=7.0,8.1Hz, Ar-H), 8.30(2H,d, J=8.0Hz, Ar-H), 8.39(2H, d, J=7.8Hz, Ar-H).

[0048] MS(ESI): Calcd for C 21 h 13 N 5 o 5 :415.09; found: [M-1] - =414.2.

[0049] Elem Anal Calcd for C 21 h 13 N 5 o 5 (415.09): C, 60.72; H, 3.15; N, 16.86; O, 19.26. Found: C, 56.51; H, 3.14; N, 15.46.

[0050] IR(KBr):υ=1631(N=N)...

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Abstract

The invention discloses 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo]benzopyran. Planar conjugated molecule 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrobenzene) azo]benzopyran provided by the invention is used as a photovoltaic cell electron Acceptor materials, through the π-πStaking effect between electron donor materials and electron acceptor materials, increase the contact area between electron donors and acceptors, shorten the diffusion distance of excitons, and improve the short-circuit current and fill factor of photovoltaic cells and photoelectric conversion rate; reduce the production cost of photovoltaic cells. An environment-friendly preparation method of benzopyran derivatives. By using this method, the synthesis cost of benzopyran derivatives is greatly reduced, and the application of benzopyran derivatives in photovoltaic cell materials will be promoted.

Description

technical field [0001] The invention relates to a novel organic semiconductor electron acceptor compound and a preparation method thereof, in particular to 2-imino-3-(4-nitrophenyl)-6-[2-(4-nitrophenyl)azo Base] benzopyran compound and its preparation method. Background technique [0002] At present, photovoltaic cell products are mainly silicon cells, because silicon is an expensive raw material, and solar silicon cells must be fixed on glass, so solar silicon cells have the disadvantages of heavy weight, high transportation and installation costs. Therefore, the development of cheap and easy-to-process thin-film photovoltaic cells has become a research hotspot. [0003] Compared with silicon photovoltaic cells, organic / polymer photovoltaic cells have the characteristics of low cost, light weight, small size, easy processing, good flexibility, and suitable for processing into large-area flat-panel devices. Improving the photoelectric conversion rate is the most important ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/04H01L51/46
CPCC07D311/04H10K85/6574Y02E10/549Y02P70/50
Inventor 张超智
Owner NANJING UNIV OF INFORMATION SCI & TECH