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Arylmethylenemalononitrile-*Base solid-state luminescent material and method

A technology of aramethylenemalononitrile and luminescent materials, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as fluorescence quenching, and achieve short reaction time, excellent solid luminescent performance, and high practicality. The effect of applying value

Active Publication Date: 2016-08-24
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional fluorescent materials have high luminous efficiency in dilute solutions, but in the solid state, due to molecular aggregation, the strong interaction between adjacent molecules produces the prohibition of transition energy levels, resulting in fluorescence quenching.

Method used

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  • Arylmethylenemalononitrile-*Base solid-state luminescent material and method
  • Arylmethylenemalononitrile-*Base solid-state luminescent material and method
  • Arylmethylenemalononitrile-*Base solid-state luminescent material and method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A kind of aryl methylene malononitrile- The preparation method of Base solid-state luminescent material comprises the following steps:

[0044] 1) Aldehyde substitution synthesis of aldehyde- Base compound, the specific method is:

[0045] 1-1) Using 4-bromoaniline as raw material and paraformaldehyde under the catalysis of trifluoroacetic acid (TFA) at -15°C for 6 days to synthesize 2,8-dibromo Base, such as figure 1 shown;

[0046] 1-2) 2,8-dibromo Base and aldehyde group are substituted to synthesize aldehyde group- Base compound, including three methods such as figure 2 shown; where the annotations in the figure are as follows:

[0047] a) n-BuLi, THF, -78°C, 1.5h;

[0048] b) DMF, -78℃-r.t., 2min;

[0049]c) n-BuLi,THF:Et 2 O=1:3, -78℃, 1.5h;

[0050] d) DMF, -78℃-r.t., 10min;

[0051] e) PhB(OH) 2 ,Pd(PPh 3 ) 4 ,2M K 2 CO 3 , toluene, 110°C;

[0052] f)(CH 3 O) 3 B, -78℃-r.t., 2min;

[0053] g) p-iodobenzaldehyde, Pd (PPh 3 ) 4 ,2M K ...

Embodiment 2

[0062] Example 2: Solid-state luminescent properties of the product

[0063] 1) UV absorption spectrum:

[0064] Aldehyde- Base compound 2, 3, 5, 6 and 2'a, 2'b, 3', 5', 6' make up 1×10 -6 mol / L dichloromethane solution, carry out ultraviolet absorption spectrum measurement, and corresponding ultraviolet absorption spectrum is as follows Figure 4 , 5 shown. Compounds 2, 3, and 6 have an obvious absorption band at 300-330nm, and compound 5 has absorption at 270-300nm, which is caused by the π-π* transition; compounds 2'a, 2'b, and 3 ', 5', 6' all have strong absorption at 350-400nm, which is caused by the π-π* transition; the absorption wavelengths of compounds 2'a, 2'b, 3', 5' and 6' are the same as those of compound 2 , 3, 5 and 6 have increased, which may be caused by the strong electron-withdrawing property of the cyano group.

[0065] 2) Solid state fluorescence:

[0066] The dichloromethane solution containing the above compound hardly shows fluorescence under th...

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Abstract

The invention discloses a synthesis method of an arylmethylene malononitrile-coupled Tr ger's Base type solid-state light-emitting material. According to the invention, 4-bromoaniline is adopted as a raw material, and is subjected to a reaction with paraformaldehyde under the catalyzing of trifluoroacetic acid and under a temperature of -15 DEG C, such that 2,8-dibromo Tr ger's Base (TB) is obtained; the 2,8-dibromo Tr ger's Base is mixed with an n-BuLi n-hexane solution in anhydrous THF; DMF is dropped in; a reaction is carried out under a temperature of -78 DEG C, such that a series aldehyde-substituted TB derivative is obtained; the obtained aldehyde-substituted TB derivative is subjected to a reaction with malononitrile in EtOH; and the reaction is carried out under the catalysis of silicon sulfonic acid, such that a novel arylmethylene malononitrile-substituted V-type TB derivative is obtained. The invention preliminarily studies on related properties of the product as the solid-state light-emitting material. According to the method, silicon sulfonic acid is adopted as the catalyst, such that the uses of strong acids such as perchloric acid and concentrated sulfuric acid are avoided. Compared to traditional methods, the reaction time is greatly reduced, and the cost is low.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to the coupling of aryl methylene malononitrile Base-type solid-state luminescent material and its synthesis method. Background technique [0002] Organic solid-state light-emitting materials are widely used in organic light-emitting diodes (OLEDs), semiconductor lasers, and fluorescent sensors. In recent years, their synthesis has become a research hotspot at home and abroad. [0003] Traditional fluorescent materials have high luminous efficiency in dilute solution, but in the solid state, due to molecular aggregation, the strong interaction between adjacent molecules produces the prohibition of transition energy levels, resulting in fluorescence quenching. [0004] Therefore, in order to obtain organic solid-state light-emitting materials with high-efficiency luminescence under solid-state conditions and expand their practical application range, it is necessary to sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D471/08
Inventor 宛瑜褚衍环黄树颖吴翚
Owner XUZHOU NORMAL UNIVERSITY
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