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Imidazo pyridine rhodamine hydrazide type cupric ion ratio fluorescence 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 , enhanced fluorescence intensity, and high sensitivity

Inactive Publication Date: 2016-07-13
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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  • Imidazo pyridine rhodamine hydrazide type cupric ion ratio fluorescence probe and application thereof
  • Imidazo pyridine rhodamine hydrazide type cupric ion ratio fluorescence probe and application thereof
  • Imidazo pyridine rhodamine hydrazide type cupric ion ratio fluorescence probe and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0016]

[0017] Concrete synthetic steps are as follows:

[0018] In a 50 mL round bottom flask, add 0.253 g (1.0 mmol) imidazo[1,5-a] pyridinecarboxylic acid, 0.290 g (1.5 mmol) 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine (EDC), 0.180g (1.5mmol) 4-dimethylaminopyridine (DMAP), 20mL anhydrous dichloromethane, react at room temperature for 30 minutes, then add 0.470g (1.0mmol) rhodamine hydrazide, room temperature The reaction was carried out for 10 hours. 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 0.48 g of an off-white solid with a yield of 68.2%.

[0019] H NMR spectrum determination: 1 HNMR (400MHz, CDCl 3 ): δ7.95(m,1H),7.72(dd,J=4.0Hz,8.0Hz,1H),7.51-7.46(m,3H),7.10-7.08(m,1H),6.7...

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 470nm and 580nm, it was found that: the compound of formula (1) has 2+ Has a unique fluorescence selectivity, adding 1 equivalent of Cu 2+ After that, the fluorescence intensity of compound 1 at 470nm was significantly reduced, and at the same time, the fluorescence intensity at 580nm was significantly enhanced, I 580 / I 470 =13.99, 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 470nm and 580nm, 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 imidazole [1,5-a] pyridine-rhodamine hydrazide derivative Cu<2+> ratio fluorescence probe.The probe is imidazole [1,5-a] pyridine substituted rhodamine hydrazide, a chemical structural formula of the probe is shown as a formula (1).The fluorescence probe has the unique fluorescence selectivity to Cu<2+> in an ethanol solution, higher sensitivity and stronger other ion interference capability and has a great application prospect.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a Cu 2+ Ratiometric fluorescent probe imidazo[1,5-a]pyridine substituted rhodamine hydrazide and its application. 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 oxidatio...

Claims

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Application Information

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