Pressure-sensitive fluorescent sensing material with aggregation-induced emission performance

An aggregation-induced luminescence and fluorescence sensing technology, which is applied in the field of chemical sensing, can solve the problems of irregularity, limited quantity of pressure-sensitive fluorescent materials, and irregular design of new materials, so as to achieve clear molecular structure regularity, make up The effect of unsustainable problems

CN111995537AActive Publication Date: 2020-11-27QUFU NORMAL UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2020-11-27

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Abstract

The invention discloses a pressure-sensitive fluorescent sensing material with aggregation-induced emission performance, and the material has a 2-(2-hydroxyarylamino)-benzoic acid parent structure, and can show the response characteristics of fluorescence quenching and fluorescence spectrum red-shift to external pressure. The pressure-sensitive fluorescent material has typical aggregation-inducedemission performance, and the molecular structure design is regular. The pressure-sensitive fluorescent sensing material is clear in structure rule and easy to design, renewable resources can be adopted as raw materials for synthesis, sustainability is achieved, and the defects of an existing pressure-sensitive fluorescent material in the aspect of molecular design are overcome.
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Description

technical field

[0001] The invention belongs to the technical field of chemical sensing, and in particular relates to a pressure-sensitive fluorescent sensing material with aggregation-induced luminescence performance. Background technique

[0002] Pressure-sensitive fluorescent materials are a class of smart materials that generate fluorescence responses to external pressure stimuli. They have important application potential in the fields of stress sensors, information storage, trademark anti-counterfeiting, and light-emitting devices. Pressure-sensitive fluorescent materials change the fluorescence emission of molecules by changing the composition of chemical bonds in molecules or the physical aggregation state of molecules, so as to realize the fluorescence response to external pressure.

[0003] Existing pressure-sensitive fluorescent materials mainly include dye-doped polymers, metal ion complexes, and small organic molecules. However, there is no consistent regularity...

Examples

Embodiment 1

[0048] Weigh 3-dehydroshikimate ethyl ester (1.00g, 5.0mmol), p-toluenesulfonic acid (0.25g, 0.50mmol), 2-amino-4-fluorobenzoic acid (0.78g, 5.0mmol) and 20mL ethanol in In the three-necked flask, the reaction was carried out under reflux for 12 hours, and the reaction was monitored by TLC. After the reaction solution was cooled, part of the solvent was removed by rotary evaporation, filtered with suction, and the filter cake was washed with ethanol to obtain a crude product, which was recrystallized with ethanol to obtain a white solid 3-(5'-fluoro-2'-carboxyanilino)-4-hydroxy Ethyl Benzoate (A).

[0049] H NMR spectrum such as figure 1 As shown in the figure, it can be known that there are carboxyl, hydroxyl, amino and other groups in the A molecule, and the NMR signal shows that there are two groups of ABC coupling systems in the molecule. The structural characterization data of the product are as follows: 1 H NMR (DMSO-d 6 ,400MHz)ppm:13.08(s,1H,COOH),10.76(s,1H),9.72(s...

Embodiment 2

[0053] Weigh 3-dehydroshikimate ethyl ester (1.00g, 5.0mmol), p-toluenesulfonic acid (0.10g, 0.50mmol), 2-amino-4-chlorobenzoic acid (0.86g, 5.0mmol) and 20mL methanol in In the three-necked flask, the reaction was carried out under reflux for 12 hours, and the reaction was monitored by TLC. After the reaction solution was cooled, part of the solvent was removed by rotary evaporation, the crude product was obtained by suction filtration, and the filter cake was washed with ethanol. The crude product was recrystallized from ethanol to obtain a light yellow solid 3-(5'-chloro-2'-carboxyanilino)-4- Ethyl hydroxybenzoate (B).

[0054] H NMR spectrum such as figure 2 As shown in the figure, it can be known that there are carboxyl, hydroxyl, amino and other groups in the B molecule; the NMR signal shows that there are two groups of ABC coupling systems in the molecule, and the structural characterization data of the product are as follows: 1 H NMR (DMSO-d 6 ,400MHz)ppm:13.23(s,1...

Embodiment 3

[0058] Weigh 3-dehydroshikimate ethyl ester (1.00g, 5.0mmol), p-toluenesulfonic acid (0.10g, 0.50mmol), 2-amino-4-bromobenzoic acid (1.08g, 5.0mmol) and 20mL ethanol in In the three-necked flask, the reaction was carried out under reflux for 12 hours, and the reaction was monitored by TLC. After the reaction solution was cooled, part of the solvent was removed by rotary evaporation, the crude product was obtained by suction filtration, and the filter cake was washed with ethanol. The crude product was recrystallized from ethanol to obtain a white solid 3-(5'-bromo-2'-carboxyanilino)-4-hydroxy Ethyl Benzoate (C).

[0059] H NMR spectrum such as image 3 As shown in the figure, it can be known that there are carboxyl, hydroxyl, amino groups and other groups in the C molecule; NMR signals show that there are two groups of ABC coupling systems in the molecule, and the structural characterization data of the product are as follows: 1 H NMR (DMSO-d 6 ,400MHz)ppm:13.24(s,1H,COOH),...