A Class of Cationic Fluorescent Probes Based on Tetraphenylethylene Structure

A tetraphenylethylene, fluorescent probe technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve problems such as limiting practical applications

Active Publication Date: 2022-04-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned fluorescent probes are usually studied in organic solvents or organic / water mixture solutions, but their practical applications are limited due to their strong aggregation-caused quenching (ACQ) effect in aqueous solutions.

Method used

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  • A Class of Cationic Fluorescent Probes Based on Tetraphenylethylene Structure
  • A Class of Cationic Fluorescent Probes Based on Tetraphenylethylene Structure
  • A Class of Cationic Fluorescent Probes Based on Tetraphenylethylene Structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The synthetic route of compound TS-1 is as follows:

[0056]

[0057] Synthesis of compound 1

[0058] Take 30mL redistilled tetrahydrofuran in a reaction flask, under the protection of argon, add zinc powder (5.2g, 80mmol) into the redistilled THF, stir for 15min under ice bath, slowly add TiCl dropwise with a syringe 4 (4.5mL, 40mmol), heated to reflux for 2h. Dissolve benzophenone (1.82g, 10mmol) and 4,4'-dihydroxybenzophenone (2.57g, 12mmol) in 20mL redistilled tetrahydrofuran, slowly add to the reaction flask, continue to heat and reflux overnight, McMurry couple occurs couplet. After the reaction, with saturated NaHCO 3 Quench the reaction with the solution, adjust the pH to 7, extract three times with 30mL dichloromethane, combine the organic phases, wash with water, anhydrous Na 2 SO 4 dry. Silica gel column chromatography (200-300 mesh column chromatography silica gel, petroleum ether:ethyl acetate / V:V=3:1) gave compound 1 (pale white solid, 1.93g, yie...

Embodiment 2

[0065] The preparation method was the same as that of compound TS-1 in Example 1, except that benzohydrazide was replaced by salicylhydrazide to obtain compound TS-2 (yellow solid, yield 85.2%).

[0066] 1 H NMR (300MHz, DMSO-d 6 )δ11.94(s,2H),11.75(s,2H),11.13(s,2H),8.51(s,2H),7.88(dd,J=7.9,1.7Hz,2H),7.46(ddd,J =8.5,7.2,1.6Hz,2H),7.18(ddd,J=17.1,9.2,3.8Hz,8H),7.07–6.92(m,10H),6.74(d,J=8.5Hz,2H).

[0067]

Embodiment 3

[0069] The synthetic route of compound TS-3 is as follows:

[0070]

[0071] Synthesis of compound 3

[0072] Take 60mL redistilled tetrahydrofuran in a reaction flask, under the protection of argon, add 9.6g zinc powder (9.6g, 0.147mol) into the redistilled THF, stir for 15min under ice bath, slowly add TiCl dropwise with a syringe 4 (8mL, 0.072mol), stirred at room temperature for 0.5h, heated to 70°C, and refluxed for 2.5h. Cool to room temperature again, add 3 mL of pyridine under ice-bath conditions, stir for 10 min, dissolve benzophenone (2.62 g, 14.4 mmol) and 4-hydroxybenzophenone (2.85 g, 14.4 mmol) in 20 mL redistilled THF, Slowly added to the reaction flask, continue heating to reflux overnight. After the reaction, with saturated NaHCO 3 Quench the reaction with the solution, adjust the pH to 7, extract three times with 30mL dichloromethane, combine the organic phases, wash with water, anhydrous Na 2 SO 4 dry. Silica gel column chromatography (200-300 colum...

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Abstract

The present invention discloses a cationic fluorescent probe based on a tetraphenylethylene structure as shown in formula I, R 1 selected from H, OH, R 2 from R 3 selected from H, OH; R 4 selected from H, OH. The cationic fluorescent probe based on the tetraphenylethylene structure of the present invention has an aggregation-induced emission effect, and tests show that it can recognize Al 3+ , Zn 2+ . Therefore, the present invention also discloses the application of the cationic fluorescent probe based on the tetraphenylethylene structure as a metal ion recognition reagent to recognize metal ions.

Description

technical field [0001] The invention relates to a fluorescent probe and its preparation method and use, in particular to a class of cationic fluorescent probes based on tetraphenylethylene structure and its preparation method and use. Background technique [0002] Aluminum is one of the most abundant metal elements on the earth, and it has a wide distribution and application. Aluminum is widely used in food additives, aluminum-based medicines, and storage and cooking utensils. After aluminum ions are absorbed, they will be distributed to all tissues of humans and animals, and eventually accumulate in bones. Iron-binding protein is the Al in plasma 3+ The main carrier of Al 3+ Can enter the brain, reach the placenta and fetus. Aluminum ions may remain in various organs and tissues for a long time before being excreted through urine. In addition, aluminum ions are considered to be a causative factor of Alzheimer's disease and are associated with damage to the central nervo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/86C07C249/16C09K11/06G01N21/64
CPCC07C251/86G01N21/643C09K11/06C09K2211/1007
Inventor 戴振亚丁志强何敬杰
Owner CHINA PHARM UNIV
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