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Novel iron ion fluorescence probe and preparation method thereof

A fluorescent probe, iron ion technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of few species and insignificant detection signals, and achieve high selectivity, obvious phenomenon, and simple preparation method. Effect

Active Publication Date: 2018-06-08
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the fluorescent probes used for the detection of iron ions have the disadvantages of fewer types and indistinct detection signals, and even fewer of them can detect iron ions in aqueous media.

Method used

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  • Novel iron ion fluorescence probe and preparation method thereof
  • Novel iron ion fluorescence probe and preparation method thereof
  • Novel iron ion fluorescence probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 7-N,N-Diethylaminocoumarin-3-carbaldehyde

[0043] Add diethylamino salicylaldehyde (0.97g, 5mmol), diethyl malonate (1.6g, 10mmol), piperidine (1.0ml) into 15mL ethanol solvent, reflux at 120°C for 18h, reduce The solution was separated by suction filtration; 20ml of concentrated hydrochloric acid and 20mL of glacial acetic acid were added thereto, stirred at 115°C for 19h, cooled to room temperature, the resulting solution was poured into 50ml of ice water, and NaOH solution was added dropwise to adjust the pH to 5. The precipitate was obtained, stirred at room temperature for 1 h, filtered with water, washed and dried to obtain an intermediate product.

[0044] a. Add 7 mL of redistilled N,N-dimethylformamide to 7 mL of POCl 3 , stirred under nitrogen protection for 35min, the solution gradually turned into a red clear solution;

[0045] b. Dissolve the intermediate product obtained in step a in 30mL N,N-dimethylformamide, add dropwise to the red c...

Embodiment 2

[0049] Preparation of Schiff base compounds (fluorescent probes for iron ions based on coumarin derivatives)

[0050] 7-N, N-diethylaminocoumarin-3-carbaldehyde (0.74g, 3mmol) and 7-amino-4-methylcoumarin (0.52g, 3mmol) were mixed at a molar ratio of 1:1 Put it into a beaker and a round-bottomed flask filled with absolute ethanol, heat the round-bottomed flask filled with 7-amino-4-methylcoumarin to 70°C, and after 3min, add 7-N,N-di Ethylaminocoumarin aldehyde was added to the round bottom flask within 1 min. After the color of the system turned orange, 3 drops of glacial acetic acid were added dropwise. After reacting for 10 h, it was cooled to room temperature, and then placed in the refrigerator for 10 min to precipitate Precipitate, filter, wash with organic solvent, and dry to obtain the target product with a yield of 64%. The resulting compound was subjected to nuclear magnetic resonance spectrum analysis, 1 H NMR (400MHz, CDCl 3 )δ: 1.26 (t, J = 7.2Hz, 6H), 2.45(d...

Embodiment 3

[0054] Detection of Photophysical Properties of the Prepared Ferric Ion Fluorescent Probe Based on Coumarin Derivatives

[0055] The compound has a fast response time ( image 3 As shown, the compound has a strong absorption at λ = 470 nm. When iron ions are added to the mixed solution in which the compound is dissolved, the original absorption peak at λ = 470 nm gradually decreases, and at the same time the absorption peak blue-shifts, and finally at λ = 450 nm A new absorption peak is formed, and the absorbance at 350 nm is continuously increasing. When the amount of iron ions is added to 4.2 equivalents, the absorption curve does not change, and the reaction reaches saturation. like Figure 4 As shown, with 350 nm as the excitation wavelength, the fluorescence intensity of the fluorescence peak of the compound at 416 nm gradually increased with the increase of the amount of iron ions added, and the final fluorescence intensity increased to 2 times of the original.

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Abstract

The invention discloses a Nnovel iron ion fluorescence probe and a preparation method thereof, and belongs to the technical field of molecular probes. The structural formula of the probe is as follows: the preparation method of the iron ion fluorescence probe is simple. The probe detects iron ions by a mode of enhancing fluorescence and obviously changing color, the iron ions can be identified ina water system highly selectively, and other metal ions (silver ions, aluminum ions, calcium ions, cobalt ions, copper ions, nickel ions, potassium ions, magnesium ions, sodium ions, nickel ions and zinc ions) are not responded. The solution obtained by adding the probe in the water system is orange; after action of the solution and the iron ions, the fluorescence of the solution is obviously enhanced, the color is changed into yellow, the selectivity on the iron ions is high, the phenomenon is obvious and identification is facilitated.

Description

technical field [0001] The present invention relates to a fluorescent probe, in particular to a coumarin derivative-based iron ion fluorescent probe and a preparation method thereof. The fluorescent probe can efficiently identify iron ions in a water system and belongs to organic small molecule fluorescent probes field. Background technique [0002] Iron ions are widely distributed in nature and are one of the important transition metal species in many biological systems and chemicals. However, after water or food is contaminated by iron ions, if the content is too high after drinking or eating and entering the human body, it will cause great damage to the heart, liver, and pancreas, and even cause life-threatening in severe cases. Therefore, it is very important to realize the rapid and sensitive detection of iron ions in aqueous media. [0003] In recent years, because small molecule organic fluorescent probes can interact with specific target analytes, the fluorescent s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643
Inventor 朱奕霖曹笃霞
Owner UNIV OF JINAN
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