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Fluorenyl fluorescent polymer and preparation method thereof

A fluorescent polymer and polymer technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as harsh test conditions, difficult operation, cumbersome process, etc., and achieve important application value and broad application prospects , the effect of accurate detection

Inactive Publication Date: 2019-11-05
HARBIN ENG UNIV
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AI Technical Summary

Problems solved by technology

The traditional detection of iron ions mainly includes o-phenanthroline method (need to use sulfuric acid, ammonia water and glacial acetic acid), sulfosalicylic acid method (need to use ammonia water), potassium thiocyanate colorimetric method (need to use concentrated sulfuric acid), process It is cumbersome and difficult to operate, must use corrosive and pungent odor solvents, and the test conditions are harsh
However, instrumental testing methods such as elemental analysis, atomic spectroscopy, plasma spectroscopy, etc., require more expensive instruments.

Method used

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  • Fluorenyl fluorescent polymer and preparation method thereof
  • Fluorenyl fluorescent polymer and preparation method thereof
  • Fluorenyl fluorescent polymer and preparation method thereof

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preparation example Construction

[0034] A preparation method route of the above-mentioned fluorenyl fluorescent polymer is as follows:

[0035]

[0036] 2. Preparation of a fluorenyl fluorescent polymer

[0037] The first step: firstly, compound I (9,9-bis(6-bromohexyl)-2,7-difluorenal) and (1S,2S)-cyclohexanediamine were used as raw materials, and the catalytic effect of anhydrous LiCl Polymer II was obtained.

[0038] In some specific embodiments: the molar ratio of the first reaction compound I to cyclohexanediamine is 1:1 to 1:3, the solvent used is dehydrated DMF, and the reaction condition is N 2 Environment, the reaction temperature environment is 100-120°C condensing and reflux, and the reaction time is 8-24h.

[0039] The second step: dissolving the obtained polymer II in a solvent, adding an aqueous solution of trimethylamine to obtain polymer III.

[0040] In some specific embodiment schemes: the solvent used for the reaction is a DMF solvent system, and the reaction conditions are N 2 envir...

Embodiment 1

[0047] Preparation of Fluorenyl Fluorescent Polymer III

[0048] Add 0.0193g (35μM) of polymer I (9,9-bis(6-bromohexyl)-2,7-difluorenaldehyde) into a 100mL reaction flask, according to the dialdehyde monomer and (1S,2S)- (+)-cyclohexanediamine monomer molar ratio is 1:2.5 for feeding, weigh 0.0125g (0.11mmoL) (1S,2S)-(+)-cyclohexanediamine, polymerization solvent is dehydrated DMF15mL, catalyst is 0.5g (0.0118moL) anhydrous LiCl, the reaction condition is N 2 Environment, temperature 110°C condensing reflux, time 12h.

[0049] After returning to room temperature, slowly add the reactant dropwise to 500mL of ice water to precipitate, centrifuge, dry, and finally wash with deionized water several times until the supernatant is clear, then vacuum-dry at 40°C for 12h to obtain 0.0145g of brown powder, namely As polymer II, the yield was 66%.

[0050] Such as figure 1As shown, the 1H NMR spectrum of polymer II is from low field to high field, and the peaks of various hydrogen p...

Embodiment 2

[0056] Fe 3+ detection method

[0057] We use the LS55 model fluorescence spectrophotometer to characterize and analyze the fluorescence properties of polymer III. The emission wavelength ranges from 330nm to 625nm, and the reaction temperature is room temperature. ex = 330nm.

[0058] Such as Figure 5 As shown, polymer III was dissolved in a buffer solution with a pH of 7 to make a sample solution with a concentration of 10 μmol / L, and then 0, 10, 20, 30, 40, 50, 60, 70, 80, 200, Fe with different concentrations of 400, 1000 and 1600μmol / L 3+ solution, and the different concentrations of Fe were explored by fluorescence spectrophotometer 3+ The effect of solution on the degree of fluorescence quenching of Polymer III. It can be seen from the figure that with Fe 3+ As the concentration increases, the fluorescence quenching effect of Polymer III is very obvious, when the Fe 3 + When the concentration increased to 1600μmol / L, the quenching percentage of polymer III was ...

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Abstract

The invention provides a fluorenyl fluorescent polymer and a preparation method thereof. The preparation method comprises the following steps that step one, (9,9-bi(6-bromine hexyl)-2,7-bifluorene aldehyde) and (1S,2S)-hexamethylene diamine are used as raw materials, and an intermediate polymer is obtained under the action of anhydrous LiCl as a catalyst; and step two, the prepared intermediate polymer is dissolved in a solvent, a trimethylamine aqueous solution is added, and the fluorenyl fluorescent polymer is obtained. According to the fluorenyl fluorescent polymer and the preparation method thereof, iron ion detection is simple, convenient and safe, the operation is convenient, selectivity is high, a result is not interfered by other ions, a linear test range is wider, and the fluorenyl fluorescent polymer and the preparation method thereof are especially applicable to the microscale and trace detection; and according to the fluorenyl fluorescent polymer and the preparation methodthereof, sensitive, rapid and accurate detection of the content of the iron ions can be realized in life bodies and under various natural and artificial aqueous solution environments, and important application value and wide application prospects are achieved in the fields such as medical treatment, industrial engineering, agriculture, building and food.

Description

technical field [0001] The invention relates to a polymer and a preparation method thereof, in particular to a fluorenyl fluorescent polymer and a preparation method thereof, and belongs to the field of metal ion detection. Background technique [0002] Iron is the fifth most abundant element on earth. It is abundant in reserves and widely used. Iron and steel materials account for 95% of the world's total metal production. Iron is also an essential element for our body and is an integral part of the composition of human and animal hemoglobin. Iron deficiency anemia occurs when the body lacks iron. However, excessive iron in cells can induce a large amount of reactive oxygen species to cause fatal damage to cells. Excessive iron ions in brain tissue can cause severe oxidative damage in the brain, and even lead to epilepsy. [0003] It is of great significance to the detection of iron ions. The traditional detection of iron ions mainly includes o-phenanthroline method (nee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C09K11/06G01N21/64
CPCC08G73/02C09K11/06C09K2211/1416C09K2211/1425G01N21/6428G01N2021/6432
Inventor 宫琳丹张博范路安郑文岐杜松辉
Owner HARBIN ENG UNIV
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