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Preparation and application of europium base polymer with long fluorescence lifetime and capable of selective recognition of anion

A europium-based polymer, fluorescence lifetime technology, applied in the field of detection, can solve problems such as short fluorescence lifetime, and achieve the effects of high sensitivity, elimination of adverse effects, and simple method

Active Publication Date: 2013-10-30
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fluorescence lifetime of these polymer sensors is relatively short. For some special applications, such as in the field of life, the polymer sensor must have the ability to resist background interference, which requires the polymer sensor to have a long fluorescence lifetime

Method used

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  • Preparation and application of europium base polymer with long fluorescence lifetime and capable of selective recognition of anion
  • Preparation and application of europium base polymer with long fluorescence lifetime and capable of selective recognition of anion
  • Preparation and application of europium base polymer with long fluorescence lifetime and capable of selective recognition of anion

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1. Preparation of polymerizable neutral ligand vinyl-phen

[0054] (1) Add 10mmol of p-hydroxybenzaldehyde and 10mmol of 4-vinylbenzyl chloride into a 100mL one-necked flask, dissolve completely with 50mL of N,N-dimethylformamide, then add 15mmol of potassium hydroxide, and stir at room temperature for 8 hours. After the reaction, the obtained solution was added to 200 mL of distilled water to obtain a large amount of precipitate, which was filtered, washed with appropriate amount of distilled water for 3 times, and dried in vacuum. In order to remove excess 4-vinylbenzyl chloride, the dried product was washed three times with an appropriate amount of n-hexane, and the resulting solid was dried to obtain the product 4-(4-vinylbenzyloxy)benzaldehyde;

[0055] (2) Take 2.1 g of 1,10-phenanthroline-5,6-dione (10 mmol) and 11.4 g of ammonium acetate (148 mmol) in a 250 mL three-neck flask with a magnetic stirring device, add 60 mL of glacial acetic acid to dissol...

Embodiment 2

[0059] Embodiment 2. The preparation of europium monomer Eu-phen

[0060]In a round-bottomed flask with a reflux device and a stirring device, dissolve 2 mmol of β-diketone in tetrahydrofuran, then add 2 mmol of hydrogen sodium oxide, and react at 65°C for 20 minutes, then add 1 mmol of β-diketone dissolved in ethanol. EuCl 3 2H 2 O solution, react at 65°C for 1h, then add 1mmol vinyl-phen containing a small amount of hydroquinone (inhibitor) into the aforementioned reaction system, then react at 65°C for 6h, cool to room temperature after the reaction, and then After vacuum removal of the solvent, washing with an appropriate amount of distilled water and ethanol, and vacuum drying, 0.87 g of europium monomer Eu-phen was obtained, with a yield of 83%. (Found: C, 49.76; H, 3.13; N, 5.32.C 44 h 32 EuF 6 N 4 o 7 S 2 [Eu-phen]requires C,49.91; H,3.05; N,5.29%). 1 H NMR (400MHz DMSO-d 6 ):3.67(s,2H,-COHCO-);5.21(s,2H,-CH 2 -);5.24-5.29(t,1H,CH 2 =CH-);5.83-5.88(t,1H,CH ...

Embodiment 3

[0064] Embodiment 3. Synthesis of long fluorescence lifetime europium-based polymer anion probe

[0065] Add 0.51 g of N-vinylcarbazole (2.6 mmol), 61.2 mg of Eu-phen (0.058 mmol) and 8 mg of AIBN into the polymerization tube, then add 3 mL of DMF to dissolve, and flush with argon 5 times, each time about 2 Minutes, finally seal the tube, stir and react at 60°C for 72 hours, dilute the obtained solution with 3mL DMF, then add dropwise to 50mL methanol for reprecipitation, repeat the reprecipitation three times, filter to obtain solid powder, and then use Soxhlet The extractor was refluxed in acetone for 48 hours, and finally the solid was dried to obtain 0.46 g of the target product, with a yield of 81%. The composition of the copolymer was obtained from elemental analysis and titration of europium ions. 1 H NMR (400MHz, CDCl 3 ):δ=8.01,7.68,6.89,6.35,4.86,3.47,3.18,2.51,0.97ppm.FTIR(KBr pellet,cm -1 ):3058,2931,1676,1628,1598,1531(C=C stretching in TTA),1482,1453,1332,1227...

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Abstract

The invention discloses a preparation and application of a europium base polymer with long fluorescence lifetime and capable of selective recognition of anion, and belongs to the technical field of detection. The method is as below: reacting a polymerizable neutral ligand vinyl-phen, a beat-diketone anion ligand and rare earth europium ions to obtain polymerizable europium monomers; adding the polymerizable europium monomers and N-vinyl carbazole monomers in a molar ratio of 1:10-100 into a polymer tube; adding an organic?solvent for complete dissolution; then adding a radical initiator; reacting at 60-80 DEG C for 10-72 h; and conducting reprecipitation, filtering, extraction, drying and solvent removal to obtain the europium base polymer with long fluorescence lifetime. The obtained europium base polymer with long fluorescence lifetime has fluorescence lifetime of 0.62-1.53 ms, good selectivity on fluorinions, acetate ions and dihydrogen phosphate ions and important application value in bioscience and environmental sciences.

Description

technical field [0001] The invention belongs to the technical field of detection, and in particular relates to the preparation and application of a long fluorescence lifetime europium-based polymer for selectively recognizing anions. Background technique [0002] Anions play an important role in human health, environment, and biochemical processes, so the design and synthesis of anion sensors with high selectivity has attracted more and more attention. Among many anions, F - It plays a vital role in nerve gas, drinking water analysis, and the purification of the radioactive element uranium. We all know that proteins play a key role in the activities of living bodies, and proteins contain a large number of carboxyl groups, so it is very important to study the recognition and sensitization of carboxyl groups in proteins. Acetate is a relatively simple carboxyl group, and research on the detection and identification of acetate helps to understand the interaction of carboxyl g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F226/12C08F230/04C09K11/06G01N21/64
Inventor 吕满庚杨朝龙许静
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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