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Indolizine-rhodamine hydrazide type cupric ion ratiometric fluorescent probe and application thereof

A ratiometric fluorescent probe and rhodamine hydrazide technology, which is applied in the fields of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problem of fewer ratiometric fluorescent probes and achieve strong anti-interference ability of other ions , high sensitivity, and great application prospects

Inactive Publication Date: 2017-05-10
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, almost all copper ion probes are single signal enhancement or weakening probes, and there are few ratiometric fluorescent probes with two or more signal response changes.

Method used

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  • Indolizine-rhodamine hydrazide type cupric ion ratiometric fluorescent probe and application thereof
  • Indolizine-rhodamine hydrazide type cupric ion ratiometric fluorescent probe and application thereof
  • Indolizine-rhodamine hydrazide type cupric ion ratiometric fluorescent probe and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016]

[0017] Concrete synthetic steps are as follows:

[0018] In a 50 mL round bottom flask, add 0.203 g (1.0 mmol) indolizine carboxylic acid, 0.290 g (1.5 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) sequentially , 0.180g (1.5 mmol) 4-dimethylaminopyridine (DMAP), 20 mL of anhydrous dichloromethane, react at room temperature for 30 minutes, then add 0.470g (1.0 mmol) rhodamine hydrazide, react at room temperature for 2-5 Hour. After the reaction was detected by TLC, 100 mL of dichloromethane was added, washed three times with 30 mL of water, the dichloromethane layer was dried over sodium sulfate, concentrated, and column chromatography gave 0.43 g of an off-white solid with a yield of 65%.

[0019] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 ): δ7.93 (m, 2H), 7.85 (s, 1H),7.53 (s, 1H), 7.47 (m, 2H), 7.08 (t, J = 4.0 Hz,1H), 6.95 (s, 1H), 6.69 (m,2H), 6.56 (s, 2H), 6.46 (m, 2H), 6.31 (m, 1H), 3.81 (s, 4H), 3.35 (q, J = 8.0Hz, 4H), 3.2...

Embodiment 2

[0021] To formula (1) compound (10 -5 M) were added 2 equivalents of Cr in the ethanol solution 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Cu 2+ ,Zn 2+ ,Cd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 445nm and 578nm, it was found that: the compound of formula (1) has 2+ Has a unique fluorescence selectivity, adding 1 equivalent of Cu 2+ Afterwards, the fluorescence intensity of compound 1 at 445nm was significantly reduced, and at the same time, the fluorescence intensity at 578nm was significantly enhanced, I 578 / I 445 = 5.3, such as figure 2 shown.

Embodiment 3

[0023] In formula (1) compound (10 -5 M) and 1 equivalent of Cu 2+ 2 equivalents of Mg were added to the ethanol solution 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 445nm and 578nm, it was found that the compound of formula (1) has strong anti-interference ability to other ions, such as image 3 shown.

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Abstract

The invention discloses an indolizine-rhodamine hydrazide derivative type Cu<2+> ratiometric fluorescent probe. The probe is indolizine substituted rhodamine hydrazide, and the chemical formula of the probe is as shown in formula (1). The fluorescent probe has unique fluorescent selectivity to Cu<2+> in an ethanol solution and is high in sensitivity, high in resistance to interference of other ions and promising in application prospect.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a Cu 2+ Rhodamine hydrazides substituted with pyrazine in ratiometric fluorescent probes and their applications. Background technique [0002] Because of its absorption and emission in the visible region, rhodamine fluorescent dyes have high fluorescence quantum yield, large molar extinction coefficient, high photostability, and easy synthesis. After structural modification, they are widely used as fluorescent probes for detecting metal ions or Research on chemical sensors. [0003] Cu 2+ It is the third most abundant transition metal element in the human body after iron and zinc. It plays a very important role in many physiological processes. An appropriate amount of copper can promote the absorption of iron, so the reduction of copper content may lead to anemia. Cu 2+ It can participate in the enzyme reaction, enzyme transcription and some oxidation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/643
Inventor 葛燕青曹晓群段桂运
Owner TAISHAN MEDICAL UNIV
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