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Preparation method of optically active AIE fluorescent material and water-based polymer thereof

A water-based polymer, fluorescent polymer technology, applied in the chemical field, can solve the problems of no light, weak fluorescence, etc.

Active Publication Date: 2020-08-18
UNIV OF ELECTRONICS SCI & TECH OF CHINA ZHONGSHAN INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the traditional organic small molecule fluorescent materials have the aggregation quenching effect (ACQ), which has strong fluorescence in dilute solution, but the fluorescence is weak or even does not emit light in the aggregated state, which greatly limits its practical application.

Method used

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  • Preparation method of optically active AIE fluorescent material and water-based polymer thereof
  • Preparation method of optically active AIE fluorescent material and water-based polymer thereof
  • Preparation method of optically active AIE fluorescent material and water-based polymer thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Embodiment 1: Preparation of aqueous optically active fluorescent polymer (II-1), its synthetic route diagram is as follows figure 1 and figure 2 shown, including:

[0046] Step 1: Add triphenylbromoethylene (7.04mmol, 2.3581g), 4-formylphenylboronic acid (8.48mmol, 1.2647g), tetrabutylammonium bromide (0.704mmol, 0.2268g), 2mol / L carbonic acid Potassium aqueous solution (12.6mL) and toluene (12.6mL) were successively added to the reaction tube, and stirred at room temperature for 0.5h; tetrakis(triphenylphosphine)palladium(0) (8.22×10 -3 mmol, 9.5 mg), the reaction tube was placed in an oil bath at 90°C under the protection of nitrogen for 48 hours; after the reaction, deionized water was added, extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, filtered, After distillation under reduced pressure, the obtained crude product was separated and purified by silica gel column chromatography (eluent: n-hexane / dichloromethane 2:1 vo...

Embodiment 2

[0060] Embodiment 2: AIE characteristic of aqueous optically active fluorescent polymer:

[0061] The solid-state fluorescence of the optically active AIE fluorescent monomer Ⅰ-1 was measured. Compared with the reported TPB fluorescent dye, its fluorescence intensity was significantly enhanced, and the fluorescence emission wavelength increased from 475nm to 496nm, and a significant red shift occurred (see image 3 ). to CDCl 3 As a solvent, the obtained compound IV-1, V-1, I-1, II-1 and II-2 1 The spectrum of H NMR is as Figure 4 As shown, each compound has its own characteristic peaks, indicating that each compound has been successfully prepared. Weigh 10 mg of water-based optically active fluorescent polymer II-1 and dissolve them in 4 mL of mixed solutions of deionized water and tetrahydrofuran with different volume ratios, and measure the fluorescence emission intensity (see Figure 5 ). In aqueous solution, there is an obvious fluorescence emission peak at 495nm, b...

Embodiment 3

[0062]Example 3: Optical activity characteristics of optically active AIE fluorescent monomer Ⅰ-1 and its amphiphilic polymer:

[0063] Weigh a certain amount of optically active AIE fluorescent monomer Ⅰ-1 and its water-based polymer, dissolve it in 20mL of acetone (concentration: 10.0mg / mL), make a uniform and transparent solution, add it to a 20cm long optical tube, and measure the fluorescent monomer and the specific optical rotation of the polymer. The calculated specific rotations of AIE fluorescent monomer Ⅰ-1 and its water-based polymer Ⅱ-2 are [α] 20 D = -9.67° and [α] 20 D =-3.74°.

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Abstract

The invention discloses a preparation method of an optically active AIE fluorescent material water-based polymer. The preparation method comprises the following steps: A, synthesizing an aldehyde group AIE fluorescent compound by utilizing a Suzuki coupling reaction between phenylboronic acid and bromobenzene; B, synthesizing a methoxy fluorescent compound by utilizing a condensation reaction between an aldehyde group and phenyl acetonitrile, and further demethylating methoxy through BBr3 to generate hydroxyl; C, introducing tertiary hydroxyl into the fluorescent compound through a nucleophilic substitution reaction between benzene hydroxyl and fatty chlorine to generate a corresponding tertiary hydroxyl AIE fluorescent compound; D, introducing an acrylic acid element into the fluorescentcompound through a selective ester exchange reaction under the catalysis of lipase B to obtain an AIE fluorescent monomer with optical activity; and E, preparing the AIE fluorescent polymer with optical activity through RAFT active polymerization. The fluorescent dye and polymer have optical activity.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a preparation method of an optically active AIE fluorescent material and a water-based polymer thereof. Background technique [0002] Optically active polymers, also known as optically active polymers, have been one of the research hotspots in the field of polymer chemistry in recent years. Optically active polymers play an important role in many fields, such as the resolution of racemic compounds, chiral recognition, asymmetric synthesis, etc., and are widely used in chiral catalysts, liquid crystals, biomedicine, optical switches and non- Fields such as linear optics show good application prospects. [0003] Most of the traditional organic small molecule fluorescent materials have the aggregation quenching effect (ACQ), which has strong fluorescence in dilute solution, but the fluorescence is weak or even does not emit light in the aggregated state, which greatly ...

Claims

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Application Information

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IPC IPC(8): C08F220/28C08F222/30C08F2/38C07C253/30C07C45/68C09K11/06C12P13/00
CPCC08F220/286C08F2/38C07C45/68C07C253/30C09K11/06C12P13/002C08F2438/03C09K2211/1007C09K2211/1425C08F222/30C07C47/548C07C255/37C07C255/36
Inventor 黄增芳陈亚利
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA ZHONGSHAN INST
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