Axially-chiral aggregation-induced luminous compound as well as preparation method and application thereof

A compound and axial chirality technology, applied in the field of axial chiral compounds and their preparation, can solve the problems of product solubility easily affected by photo-oxidation, long synthetic route steps, large synthetic workload, etc., and achieves correct structure, good stability, The effect of high product yield

Active Publication Date: 2017-05-24
李再高
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the synthetic route is long and the synthetic workload is heavy, and the enhancement of the intermolecular interaction of the obtained compound may easily lead to induced luminescence quenching, susceptible to photooxidation, and reduced product solubility.

Method used

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  • Axially-chiral aggregation-induced luminous compound as well as preparation method and application thereof
  • Axially-chiral aggregation-induced luminous compound as well as preparation method and application thereof
  • Axially-chiral aggregation-induced luminous compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The reaction formula is as follows:

[0027]

[0028] Add 1.0g (2.9mmol) 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde racemate, 50mL ethanol, 0.94g (6.0mmol) diethyl malonate and 0.25g (2.9mmol) piperidine were heated to reflux for 24h, cooled to room temperature, a solid precipitated, filtered, and dried to obtain 1.1g of a yellow powder product with a yield of 70%.

[0029] In the above examples, the racemate of 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde was replaced by S-type 2,2'-dihydroxy-[1, 1'-binaphthyl]-3,3'-dialdehyde, and the other steps are exactly the same as those in the above examples to obtain the S-type product.

[0030] In the above examples, the racemate of 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde was replaced by R-type 2,2'-dihydroxy-[1, 1'-binaphthyl]-3,3'-dialdehyde, and the other steps are exactly the same as in the above examples to obtain the R-type product.

[0031] The structure detection result of this compound is as f...

Embodiment 2

[0037] The reaction formula is as follows:

[0038]

[0039]Add 1.0g (2.9mmol) 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde racemate, 50mL ethanol, 0.78g (6.0mmol) ethyl acetoacetate and 0.25g (2.9mmol) piperidine were heated to reflux for 24h, cooled to room temperature, a solid precipitated, filtered and dried to obtain 1.0g of a yellow powder product with a yield of 73%.

[0040] In the above examples, the racemate of 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde was replaced by S-type 2,2'-dihydroxy-[1, 1'-binaphthyl]-3,3'-dialdehyde, and the other steps are exactly the same as those in the above examples to obtain the S-type product.

[0041] In the above examples, the racemate of 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dialdehyde was replaced by R-type 2,2'-dihydroxy-[1, 1'-binaphthyl]-3,3'-dialdehyde, and the other steps are exactly the same as in the above examples to obtain the R-type product.

[0042] The structure detection result of this compound is as f...

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Abstract

The invention discloses an axially-chiral fluorescence dye compound having a characteristic of aggregation-induced luminescence. The invention further discloses a preparation method of the compound. The compound disclosed by the invention has the advantages of being simple and convenient to synthetize, high in product yield, simple to purify and the like, the synthetized compound concurrently has the characteristics of an axially-chiral structure of binaphthol and the characteristics of fluorescence of a coumarin structure, has the characteristics of long transmitted wave length, larger stocks shift and aggregation-induced luminescence, presents yellow fluorescence at solid state, and has potential application in the field of organic luminescent materials and fluorescence test.

Description

[0001] 【Technical field】 [0002] The invention relates to the field of fluorescent materials, in particular to an axial chiral compound with aggregation-induced luminescent properties and a preparation method and application thereof. [0003] 【Background technique】 [0004] Compared with traditional inorganic semiconductor materials, new organic light-emitting semiconductor functional materials used in solid state or aggregated state have the advantages of high sensitivity, good device flexibility, low cost, small device size, large area preparation and easy integration. The field of optoelectronic research has received more and more attention (Chem. Phys. Lett., 1974, 29, 277, Chem. Rev. 2007, 107, 1011). In addition to organic optoelectronic devices, organic light-emitting materials are used in information storage (J.Mater.Chem.C,2013,1,3376; Chem.Soc.Rev.,2013,42,857; Adv.Mater.,2013,25,378; Chem.Soc. Rev., 2013, 42, 8895.) and biological sciences (Chem. Rev., 2013, 113, 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B57/02
CPCC09B57/02C09K11/06C09K2211/1088
Inventor 胡志强陈绍晋王鲲鹏江一牛翔刘威葛兆海陈聚朋雷洋郑文君
Owner 李再高
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