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A fluorescent functionalized carbonate, its preparation method and application, and fluorescent polycarbonate prepared therefrom

A technology of polycarbonate and carbonate, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., to achieve broad application prospects and research value, excellent AIE performance, and high yield effects

Inactive Publication Date: 2020-05-08
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is still challenging to combine the strong and stable fluorescence of AIE with the excellent biological properties of aliphatic polyesters

Method used

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  • A fluorescent functionalized carbonate, its preparation method and application, and fluorescent polycarbonate prepared therefrom
  • A fluorescent functionalized carbonate, its preparation method and application, and fluorescent polycarbonate prepared therefrom
  • A fluorescent functionalized carbonate, its preparation method and application, and fluorescent polycarbonate prepared therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Synthesis of fluorescent functionalized carbonate (TPETC)

[0041] Synthesis of 4-(1,2,2-triphenylvinyl)phenol

[0042]

[0043] Vacuumize the 250mL reaction bulb for three times, and add 150mL of tetrahydrofuran and 2.76g of activated zinc powder into the reaction bulb under the protection of argon. Then place the reaction bulb in an ice-water bath and stir for half an hour; then gradually add 0.24 mL of titanium tetrachloride using a syringe within half an hour to obtain a dark brown reaction solution. After the reaction solution returned to room temperature, it was slowly heated up and refluxed for 2 hours; after returning to room temperature again, 1.92 g of benzophenone and 2.10 g of 4-hydroxybenzophenone were added, and refluxed for 20 hours. The reaction was quenched with 100 mL of 10% potassium carbonate aqueous solution, and THF was removed by rotary evaporation. Finally, the product was extracted with dichloromethane, dried, concentrated, and se...

Embodiment 2

[0056] Example 2 AIE performance characterization of TPETC in solution environment

[0057] Water was slowly added to a solution of TPETC in dimethyl sulfoxide (DMSO). Prepare a series of DMSO-H with a concentration of 50 μM 2 O(100:0~1:99) mixture. image 3 Fluorescence spectra of a series of mixtures. When the proportion of water increases from 0% to 40%, the mixed system has almost no fluorescence; when the proportion of water reaches 50%, the fluorescence intensity of the mixed system increases sharply, and then the fluorescence intensity further increases with the increase of water content ,Such as Figure 4 shown. Figure 5 It is the change of the value of the fluorescence intensity at the maximum emission wavelength of 485nm in the emission spectrum.

Embodiment 3

[0058] Embodiment 3 Preparation of TPETC amphiphilic block polymer

[0059] Under argon protection, mPEG2000 (0.03g), TPETC (0.18g) were added to the reaction flask. The reaction flask was then evacuated at 45 °C for 2.5 h. Then DBU (0.01mmol) and dichloromethane (0.7mL) were added into the reaction flask and reacted at room temperature for 72h. Glacial ether was precipitated to obtain fluorescent polycarbonate. Figure 4 It is the proton nuclear magnetic resonance spectrum of the product. Through the ratio of the peak area of ​​the mPEG characteristic peak at 3.63ppm to the methylene characteristic peak on the carbonate at 4.10ppm, the degree of polymerization of TPETC is about 18.5, and the molecular weight of fluorescent polycarbonate is about 12700. . 1 H NMR (400MHz, CDCl 3 ,δ,ppm):7.20-6.95(m,15H),6.91(br,2H),6.66(br,2H),4.40(br,2H),4.10(br,8H),3.63(br,9.8H) ,1.50(br,2H),0.88(br,3H).

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Abstract

The invention discloses fluorescence-functionalized carbonate, having a structural formula that is shown in the description. The invention also discloses a method of preparing the fluorescence-functionalized carbonate. The method comprises the steps of dissolving trimethylolpropane-imidazole-carbonate and 2-(4-(1,2,2-triphenylvinyl)phenoxy)ethanol in acetone, reacting at 45-65 DEG C under the catalytic action of cesium fluoride, and isolating after full reaction to obtain the fluorescence-functionalized carbonate of formula I. The invention also discloses application of the fluorescence-functionalized carbonate in optical materials, and fluorescent polycarbonate prepared from the fluorescence-functionalized carbonate; as AIE (aggregation-induced emission) macromolecule, the fluorescent polycarbonate is applicable to the preparation of degradable bio-probes with adjustable fluorescent brightness.

Description

technical field [0001] The invention relates to the technical field of aggregation-induced luminescent materials, in particular to a fluorescent functionalized carbonate, a preparation method and application thereof, and a fluorescent polycarbonate prepared therefrom. Background technique [0002] Optical imaging can sensitively and dynamically detect fluorescent signals of different colors. Now, a variety of fluorescent materials have been developed for optical imaging, such as organic small molecule dyes and quantum dots. For traditional organic fluorescent small molecules, in practical applications, the concentration of fluorescent molecules needs to be limited, and as a result, it is difficult to improve the detection sensitivity. Tang Benzhong's research group discovered a class of substances that hardly emit light in the dispersed state, but the fluorescence is greatly enhanced in the aggregated state, namely "aggregation-induced emission (AIE)". On the basis of retai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/06C09K11/06C08G64/30C08G64/06
CPCC07D319/06C08G64/06C08G64/305C09K11/06C09K2211/1088
Inventor 郎美东张俊勇张琰
Owner EAST CHINA UNIV OF SCI & TECH
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