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Preparation method of chiral fluorescence sensor with large-volume side group amylase derivative

A fluorescence sensor and amylose technology are applied in the field of preparation of functional polymer materials to achieve the effects of high yield, simple synthesis process and easy control.

Pending Publication Date: 2018-11-06
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are relatively few studies on the preparation of chiral fluorescent sensors based on polymers, and there is no report on the development of chiral fluorescent sensors using polysaccharide derivatives with large bulky side groups.

Method used

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  • Preparation method of chiral fluorescence sensor with large-volume side group amylase derivative
  • Preparation method of chiral fluorescence sensor with large-volume side group amylase derivative
  • Preparation method of chiral fluorescence sensor with large-volume side group amylase derivative

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Embodiment Construction

[0019] The following examples describe the present invention in more detail.

[0020] 1. Add 24mmol 4-ethoxyphenylboronic acid, 10mmol 2,5-dibromoaniline, 60mmol sodium carbonate, 0.4mmol tetrakis (triphenylphosphine) palladium into a two-neck flask, and then add 75ml volume ratio 2 / 1 A mixed solution of dioxane and water; the reaction system is heated to 80° C. and stirred for 32 hours, and then the reaction ends. Then the temperature of the reaction system was lowered to room temperature, and the crude product was obtained after removing the solvent. The crude product was purified by column chromatography to obtain pure light yellow powder of 2,5-bis(4'-ethoxyphenyl)aniline. The yield was 83.3%.

[0021] 2. Take 9mmol of 2,5-bis(4'-ethoxyphenyl)aniline in a two-necked flask, add 14.6mL of a 20wt% sulfuric acid and water mixed solution, heat at 60℃ for 2h until the sample is completely dissolved; Slowly add 3ml of 3.3mol / L sodium nitrite solution to the reaction flask under ice...

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Abstract

The invention provides a preparation method of a chiral fluorescence sensor with a large-volume side group amylase derivative. The preparation method comprises the following steps: taking 2,5-dibromoaniline and 4-ethoxybenzeneboronic acid as raw materials, and synthesizing 2,5-di(4'-ethyoxyl phenyl) aniline through a Suzuki coupling reaction; synthesizing 2,5-di(ethyoxyl phenyl) bromobenzene through a Sandmeyer reaction; and synthesizing 2,5-di(4'-ethyoxyl phenyl) phenylboronic acid with a one-pot method through reactions such as Grignard; then, taking amylase as a reaction substrate, taking 4-bromophenyl isocyanate as a derivatization reagent, synthesizing amylase-tri(4-bromophenyl carbamate) through a traditional esterification method, and finally synthesizing amylase-tri(4-(2'-diethoxypara-terphenyl)) phenyl carbamate) through a Suzuki coupling reaction. The preparation method is clear and practicable in synthetic route, mature in technology and easy to realize, and can be used forlarge-scale batch production.

Description

Technical field [0001] The invention relates to a method for preparing a functional polymer material, in particular to a method for preparing a chiral fluorescent sensor. Background technique [0002] When used as chiral stationary phases (CSPs) for high performance liquid chromatography, amylose phenyl carbamate derivatives show excellent chiral recognition ability. Although it has a wide range of applications in chiral stationary phase materials, it still has few practical applications in other chiral functional materials. Due to its simplicity, rapidity and high sensitivity, the chiral recognition method using fluorescence response as the output signal is considered to be one of the most direct and efficient technologies for rapid recognition and response of chiral molecules. Up to now, people have used various small molecules to develop various chiral fluorescence sensors, such as those based on bis(oxazolinyl)phenol, toluene, 1,8-diheteroarylnaphthalene and binaphthyl compo...

Claims

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Application Information

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IPC IPC(8): G01N21/64C08B33/00
CPCC08B33/00G01N21/6428
Inventor 沈军毕婉莹王凡刘博
Owner HARBIN ENG UNIV
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