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A kind of optically active aie fluorescent material and preparation method of water-based polymer

A technology of fluorescent polymers and fluorescent materials, applied in the chemical industry, can solve the problems of no light emission and weak fluorescence

Active Publication Date: 2022-07-01
UNIV OF ELECTRONICS SCI & TECH OF CHINA ZHONGSHAN INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of optically active aie fluorescent material and preparation method of water-based polymer
  • A kind of optically active aie fluorescent material and preparation method of water-based polymer
  • A kind of optically active aie fluorescent material and preparation method of water-based polymer

Examples

Experimental program
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Embodiment 1

[0046] Example 1: Preparation of aqueous optically active fluorescent polymer (II-1), the synthetic route of which is as follows figure 1 and figure 2 shown, including:

[0047] Step 1: Triphenyl bromide (7.04mmol, 2.3581g), 4-formylbenzeneboronic acid (8.48mmol, 1.2647g), tetrabutylammonium bromide (0.704mmol, 0.2268g), 2mol / L carbonic acid Potassium aqueous solution (12.6 mL) and toluene (12.6 mL) were added to the reaction tube in turn, and stirred at room temperature for 0.5 h; tetrakis(triphenylphosphine)palladium(0)(8.22×10 -3 mmol, 9.5mg), the reaction tube was put into an oil bath at 90°C for 48h under nitrogen protection; 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 chromatography (eluent: n-hexane / dichloromethane 2:1 volume ratio) to obtain 4-(1,2,2-tri...

Embodiment 2

[0061] Example 2: AIE properties of aqueous optically active fluorescent polymers

[0062] The solid fluorescence of optically active AIE fluorescent monomer I-1 was measured. Compared with the reported TPB fluorescent dyes, its fluorescence intensity was significantly enhanced, and the fluorescence emission wavelength increased from 475nm to 496nm, which had an obvious red shift (see image 3 ). with CDCl 3 as solvent, the obtained compounds IV-1, V-1, I-1, II-1 and II-2 1 The HNMR spectrum is as Figure 4 As shown, each compound appeared its own characteristic peak, indicating that each compound was 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 in different volume ratios, and measure the fluorescence emission intensity (see Figure 5 ). In the aqueous solution, there is an obvious fluorescence emission peak at 495 nm, while there is almost no...

Embodiment 3

[0063]Example 3: Optical properties of optically active AIE fluorescent monomer I-1 and its amphiphilic polymer

[0064] Weigh a certain amount of optically active AIE fluorescent monomer I-1 and its water-based polymer, dissolve it in 20 mL of acetone (concentration is 10.0 mg / mL), prepare a uniform and transparent solution, add it to a 20 cm long optical rotation tube, and measure the fluorescent monomer. and the specific optical rotation of the polymer. The calculated specific optical rotations of the AIE fluorescent monomer I-1 and its aqueous 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, comprising the following steps: A. synthesizing an aldehyde-based AIE fluorescent compound by using the Suzuki coupling reaction of phenylboronic acid and bromobenzene; B. using an aldehyde group and phenylacetonitrile The condensation reaction between the methoxyl fluorescent compounds was synthesized, which was further processed by BBr 3 Demethylation of the methoxy group to generate a hydroxyl group; C. Through the nucleophilic substitution reaction between the phenyl hydroxyl group and aliphatic chlorine, the tertiary hydroxyl group is introduced into the fluorescent compound to generate the corresponding tertiary hydroxyl group AIE fluorescent compound; D. By lipase B. The selective transesterification reaction catalyzed by the introduction of acrylic acid group into the fluorescent compound to obtain the AIE fluorescent monomer with optical activity; E. The AIE fluorescent polymer with optical activity is prepared by RAFT active polymerization. The fluorescent dyes and polymers are optically active.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a preparation method of an optically active AIE fluorescent material and an aqueous 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 separation of racemic compounds, chiral recognition, asymmetric synthesis, etc., and are widely used in chiral catalysts, liquid crystals, biomedicine, optical switches and Linear optics and other fields show good application prospects. [0003] Most of the traditional organic small molecule fluorescent materials have aggregation quenching effect (ACQ), which has strong fluorescence in dilute solution, but weak fluorescence or even no light in the aggregated state, which greatly limits its practical applicatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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