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Pyridino-benzo imidazole cupric ion rate fluorescence probe and application thereof

A technology of ratio fluorescent probe and benzimidazole, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problem of fewer ratio fluorescent probes, achieve strong anti-interference ability of other ions, Effect of high sensitivity and enhanced fluorescence intensity

Inactive Publication Date: 2016-09-07
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Pyridino-benzo imidazole cupric ion rate fluorescence probe and application thereof
  • Pyridino-benzo imidazole cupric ion rate fluorescence probe and application thereof
  • Pyridino-benzo imidazole cupric ion rate fluorescence 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] Add 0.226 g (1.0 mmol) pyridobenzimidazole carboxylic acid, 0.290 g (1.5 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide ( EDC), 0.180g (1.5 mmol) 4-dimethylaminopyridine (DMAP), 20 mL of anhydrous dichloromethane, reacted at room temperature for 30 minutes, then added 0.470g (1.0 mmol) rhodamine hydrazide, reacted at room temperature for 2 -5 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 0.51 g of an off-white solid with a yield of 75%.

[0019] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 ):δ8.45 (d, J = 8.0 Hz,1H), 8.05(d, J = 8.0 Hz,1H),7.94 (m, 2H), 7.60 (m, 1H), 7.48 (m, 3H),7.10 (m, 1H),6.80 (d, J = 4.0 Hz,1H), 6.44 (s,1H), 6.34 (d, J = 4.0 Hz,1H), 4.04 (m, 2H),3.68 (s, 2H), 3.51 (d, J = 4.0 Hz,2H...

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 436nm 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 436nm was significantly reduced, and at the same time, the fluorescence intensity at 580nm was significantly enhanced, I 580 / I 436 = 30.4, 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 436nm 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 pyridino-benzo imidazole-rhodamine hydrazide derivative Cu2+ rate fluorescence probe. The probe is rhodamine hydrazide substituted by pyridino-benzo imidazole, and the chemical formula of the probe is shown in formula (1). The fluorescence probe has unique fluorescence selectivity to Cu2+ in an alcohol solution, has high sensitivity, high capacity of resisting interference of other ions and has huge application prospects.

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 pyridobenzimidazole 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 oxidation-r...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06G01N21/64
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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