A kind of binaphthol derivatives based on th 4+ Fluorescence recognition material and its preparation method and application

A binaphthol and fluorescence recognition technology, which is applied in the preparation of luminescent materials, organic compounds, and material analysis through optical means, can solve the problems of unfavorable water system heavy metal ion detection, etc., to solve the problem of easy falling off and non-reusable problems, improved specificity identification, and low detection limit

Inactive Publication Date: 2020-01-03
NANHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the usual high-resolution materials have no specific recognition ability for specific metals and are not conducive to the detection of heavy metal ions in water systems due to the problem of water solubility.

Method used

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  • A kind of binaphthol derivatives based on th <sup>4+</sup> Fluorescence recognition material and its preparation method and application
  • A kind of binaphthol derivatives based on th <sup>4+</sup> Fluorescence recognition material and its preparation method and application
  • A kind of binaphthol derivatives based on th <sup>4+</sup> Fluorescence recognition material and its preparation method and application

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preparation example Construction

[0037] The invention discloses a compound based on binaphthol derivatives Th 4+ Preparation methods of fluorescent recognition materials, such as figure 1 shown, including the following steps:

[0038] Step 1, preparation of intermediate product (R)-2,2'-dimethoxy-1,1'-binaphthyl ether (abbreviated as RDB), its specific synthetic route is as follows:

[0039]

[0040] Specifically follow the steps below:

[0041] At 0°C, a mixed solution of NaH in anhydrous tetrahydrofuran (THF) and anhydrous N, N' dimethylformamide (DMF) was added dropwise to anhydrous tetrahydrofuran solution of R-binaphthol; , THF and DMF volume ratio (ml:ml) in the mixed solution of anhydrous THF and anhydrous DMF are 2: 1-4: 1; The mass volume ratio (g of the mixed solution of NaH and anhydrous THF and anhydrous DMF : ml) is 1:40-2:40; after the dropwise addition, react at room temperature for 0.5-1.5h, wherein, the volume concentration of R-binaphthol is 0.85M; after the reaction is completed, MOMC...

Embodiment 1

[0052] Step 1. Prepare the intermediate product [(R)-2,2'-dimethoxy-1,1'-binaphthyl methyl ether] (RDB), specifically according to the following steps:

[0053] At 0°C, 2g NaH (3mmol) was dissolved in 50mL of anhydrous THF and 30mL of anhydrous DMF, and then the mixed solution was added dropwise to R-binaphthol in anhydrous THF solution, and reacted at room temperature 1h. 5 mL MOMCl (chloromethyl methyl ether) was added dropwise to the product system and kept at room temperature for 4 h, then the reaction was quenched with water. The reacted mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated NaCl solution and anhydrous MgSO 4 After drying, the solvent was distilled off under reduced pressure. The resulting solid was recrystallized with MeOH to obtain 3.32 g of a white solid with a yield of 92%, and RDB was prepared;

[0054] Step 2. Prepare the target product 1-bis(3'-(2'-hydroxyl-4'-(2"-hydroxyl-1"-naphthyl)naphthyl)) benzy...

Embodiment 2

[0063] A kind of based on binaphthol derivative Th 4+ A method for preparing a fluorescent recognition material, comprising the following steps:

[0064] Step 1. Preparation of the intermediate product (R)-2,2'-dimethoxy-1,1'-binaphthyl methyl ether, referred to as RDB, specifically implemented according to the following steps:

[0065] Dissolve NaH in a mixed solution of anhydrous THF and anhydrous DMF at 0°C, wherein the volume ratio (ml:ml) of THF to DMF in the mixed solution of anhydrous THF and anhydrous DMF is 2:1; The mass volume ratio (g:ml) of the mixed solution of NaH and anhydrous THF and anhydrous DMF is 1:40; Reaction 1.5h. Wherein, the volume concentration of R-binaphthol is 0.85M; after the reaction is completed, MOMCl (chloromethyl methyl ether) is added dropwise to the product system and kept at room temperature for 4h. The volume ratio (ml:ml) of MOMCl (chloromethyl methyl ether) to the anhydrous THF solution of R-binaphthol is 2:3; Then quench the reactio...

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Abstract

The invention discloses a Th<4+> fluorescent identification material based on a 1,1'-bi-2-naphthol derivative and a preparation method and application of the fluorescent identification material. The preparation method includes the following steps: preparing an intermediate product (R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl which is called RDB for short; preparing a target product 1-bis(3'-(2'-hydroxy-4'-(2'-hydroxy-1'-naphthyl)naphthyl))benzyl alcohol which is called RDB-B for short; preparing a complex of Th<4+> and the 1-bis(3'-(2'-hydroxy-4'-(2'-hydroxy-1'-naphthyl)naphthyl))benzyl alcohol; and preparing the Th<4+> fluorescent identification material based on the 1,1'-bi-2-naphthol derivative. The preparation method provided by the invention can synthesize the high-molecular polymericmaterial, the material can be reused, the internal structure is not damaged, and the problems that a small-molecular fluorescent material is easy to drop and cannot be reused are solved.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, in particular, relates to a compound based on binaphthol derivatives Th 4+ Fluorescence recognition material and its preparation method and application. Background technique [0002] Thorium is a radioactive element widely distributed on the earth's crust, and it has a wide range of uses in industrial and agricultural production such as the nuclear industry, aerospace, and medical care. However, the mining and use of thorium produces a large amount of waste, which is toxic and radioactive, and is one of the most dangerous environmental pollutants that seriously endangers health. If not handled properly, it will cause serious harm. Studies have shown that continuous exposure to thorium may increase the risk of lung, pancreatic or bone cancer in humans and cause changes in genetic material. Therefore, a simple and convenient detection method for Th 4+ method is particularly important....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08L27/06C08K13/02C08K3/22C08K5/378C08K5/138C08K5/521C08J3/12C07C41/16C07C43/235C07C37/055C07C39/14C07F5/00C09K11/06G01N21/64
CPCC07C37/055C07C41/16C07F5/003C08J3/12C08J2327/06C08K3/22C08K5/138C08K5/378C08K5/521C08K13/02C08K2003/222C09K11/06C09K2211/182G01N21/6402C08L27/06C07C43/235C07C39/14
Inventor 王宏青谭艳红刘波王榆元伍徐孟
Owner NANHUA UNIV
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