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Amphiphilic temperature-sensitive block copolymer-based sensor, as well as preparation method and application thereof

A block copolymer and amphiphilic technology, applied in the field of chemical fluorescent materials, can solve the problems of poor water solubility, low sensitivity reliability and weak biocompatibility of metal ion sensors, achieve excellent water solubility and improve detection sensitivity , the effect of fluorescence intensity enhancement

Active Publication Date: 2017-06-20
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many of these sensors have overcome the shortcomings of metal ion sensors such as poor water solubility, weak biocompatibility, low sensitivity and reliability, and high detection limit. However, most of them still have more or less such problems.
The development of new water-soluble, high-sensitivity, and biocompatible photochemical sensors is currently a research hotspot in this field. However, many difficulties cannot be overcome for traditional photochemical sensors to achieve such complex functions.

Method used

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  • Amphiphilic temperature-sensitive block copolymer-based sensor, as well as preparation method and application thereof
  • Amphiphilic temperature-sensitive block copolymer-based sensor, as well as preparation method and application thereof
  • Amphiphilic temperature-sensitive block copolymer-based sensor, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: Preparation of salicylaldehyde hydrazone SH

[0059]

[0060] References (G. L. Backes, D. M. Neumann, B. S. Jursic, Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides, Bioorg. Med. Chem. 22(17) (2014) 4629-4636.).

[0061] (1.18 g, 20.00 mmol) hydrazine hydrate was dissolved in ethanol (20.00 ml), and a mixed solution of salicylaldehyde (2.45 g, 20.00 mmol) and ethanol (10.00 ml) was added dropwise, and the reaction temperature was raised to 70.0 ℃, react for 30 min. After the reaction, the solvent was removed to obtain a crude product, which was washed three times with cold diethyl ether (20.00 ml) to obtain a white scaly solid product (2.04 g, yield: 75 %). 1 H NMR (CDCl 3 , δ, ppm; Fig. S1 (a)): 8.71 (1H, ArCH=N-), 7.31-7.44 (1H, -C(CH 3 )=CHH), 6.92-7.07 (4H, ArH).

Embodiment 2

[0062] Example 2: Preparation of fluorescent probe SHMA based on salicylaldehyde hydrazone

[0063]

[0064] Dissolve salicylaldehyde hydrazone (1.50 g, 11.00 mmol) in dry CH 2 Cl 2 (20.00 ml), methacryloyl chloride (3.45 g, 33.00 mmol) was added dropwise in an ice-water bath. Reflux at 25.0 °C for 3 h. The organic layer was dried with anhydrous sodium sulfate, and filtered, and the filtrate was rotary evaporated to obtain a crude product, and finally the crude product was passed through a silica gel column with dichloromethane as the developing solvent to obtain a gray-green solid powder. 1 H NMR (CD 3 OD, δ, ppm; Fig. 2): 8.48 (1H, ArCH=N-), 6.96-7.44(4H, ArH), 5.85 (1H, -C(CH 3 )=CHH), 5.58 (1H, -C(CH 3 )=CHH), 2.04 (3H, CH 3 C-).

Embodiment 3

[0065] Embodiment 3: the preparation of RAFT reagent BTPA

[0066]

[0067] Refer to literature (J. Skey, R. K. O'Reilly, ChemInform Abstract: Facile One-PotSynthesis of a Range of Reversible Addition-Fragmentation Chain Transfer (RAFT) Agents, Chem Commun. 40(4) (2009) 4183-4185.) :

[0068] 3-Mercaptopropionic acid (MPA) (2.50 ml, 28.65 mmol) was added dropwise to KOH (1.84 mol / L, 31.25 ml) aqueous solution, and then CS 2 (3.65ml, 28.65mmol). After stirring at room temperature for 5 h, benzyl bromide (4.95 g, 28.65 mmol) was added dropwise and heated to 80.0 °C for 12 h. After the reaction, the reaction solution was cooled to room temperature, extracted with chloroform (90.00 ml), then acidified by adding excess hydrochloric acid, and the organic phase was washed with distilled water repeatedly, and the solvent was evaporated to dryness to obtain a yellow solid (3.20 g, yield: 40.9%). 1 H NMR (CDCl 3 , δ, ppm, TMS; Fig. 2): 7.33 (5H,ArH), 4.64 (2H, ArCH 2 -), 3.65 (...

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Abstract

The invention relates to an amphiphilic temperature-sensitive block copolymer-based sensor, as well as a preparation method and application thereof, and belongs to the technical field of chemiluminescent materials. The sensor is named as PEO113-b-P(NIPAM-co-SHMA)65 probe. The preparation method comprises the following steps: preparing a salicylaldehyde-hydrazone-based fluorescent probe SHMA at first, and adding a magneton, NIPAM, a methoxy polyethylene glycol-based macromolecular chain transfer agent, AIBN and 1,4-dioxane for mixing; after reaction in an oil bath, performing dilution with the 1,4-dioxane, and cyclically and repeatedly performing precipitation-dissolution in an excessive amount of ethyl ether for multiple times; obtaining a light yellow solid powder product. The sensor provided by the invention is extremely high in water solubility, temperature sensitivity, biocompatibility, multi-selectivity and sensitivity, and Al<3+> and Zn<2+> can be distinguished by virtue of the colors of fluorescence and fluorescence intensities at different time points.

Description

technical field [0001] The invention relates to a sensor based on an amphiphilic temperature-sensitive block copolymer, a preparation method and application thereof, and belongs to the technical field of chemical fluorescent materials. Background technique [0002] Aluminum is the most abundant metallic element known to exist in the earth's crust, yet it is not an essential element for the human body. Long-term intake of high concentrations of aluminum ions can lead to diseases such as nervous system damage, hearing loss, memory loss, and Alzheimer's disease. However, in real life, the use of aluminum-containing food additives and aluminum-containing kitchen utensils exposes human health to the hazards of aluminum ions. Zinc is one of the essential trace elements for the human body, and it plays an extremely important role in physiological processes such as human growth and development, reproductive inheritance, immunity, and endocrine. Zinc deficiency can lead to diseases...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F220/54C08F220/60C08G65/334G01N21/64C09K11/06
CPCC08F220/54C08F220/60C08F293/005C08F2438/03C08G65/3344C09K11/06C09K2211/1425C09K2211/1433C08F220/603G01N21/6428G01N21/643G01N2021/6443
Inventor 安宝东王赟齐越韩娟鲍煦王蕾李程倪良
Owner JIANGSU UNIV
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