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Fluorescent probe based on rhodamine-indole derivative as well as preparation method and application of fluorescent probe

A technology of indole derivatives and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of strong selectivity, easy availability of raw materials, and wide application value

Inactive Publication Date: 2017-12-15
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, palladium ions in the body can interact with DNA, thiol-containing amino acids, proteins and vitamin B6, resulting in disease

Method used

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  • Fluorescent probe based on rhodamine-indole derivative as well as preparation method and application of fluorescent probe
  • Fluorescent probe based on rhodamine-indole derivative as well as preparation method and application of fluorescent probe
  • Fluorescent probe based on rhodamine-indole derivative as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Rhodamine-Indole Derivatives

[0025]

[0026] Indole-3-carboxylic acid (161mg, 1mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (191mg, 1mmol) and 4-dimethylaminopyridine (122mg, 1mmol) was dissolved in dichloromethane (20ml), then rhodamine B ethylenediamine (456mg, 1mmol) was added, refluxed at normal pressure for 12h, concentrated in vacuo, purified by silica gel column chromatography [CH 2 Cl 2 / CH 3 OH=100:1 (v / v)] to obtain a yellow solid which is the target product, and the yield of the target product is 69%.

[0027] Rhodamine-indole derivative NMR analysis results are as follows:

[0028] Proton NMR spectrum: 1 H NMR (400MHz, d 6 -DMSO),δ(ppm):8.01-8.03(t,1H,NH),7.75-7.76(m,1H,Aryl-H),7.44-7.46(m,2H,Aryl-H),7.30-7.32( m,1H, Aryl-H),7.02-7.06(t,1H,Aryl-H),6.94-6.97(m,1H,Aryl-H),6.58-6.60(m,1H,Aryl-H),6.39- 6.41(m,1H,Aryl-H),6.30-6.37(m,7H,Aryl-H),3.24-3.29(d,8H,4CH 2 ),3.13-3.17(m,2H,CH 2 ),2.92-2.97(m,2H,CH 2 ),1.02-...

Embodiment 2

[0031] Determination of Optical Properties of Rhodamine-Indole Derivatives on Divalent Palladium Ions

[0032] The rhodamine-indole derivatives prepared in Example 1 above were used as probes in acetonitrile / water (volume ratio 9:1) medium to prepare a molar concentration of 5×10 -6 mol / L solution, respectively, at a molar concentration of 5×10 -6 mol / L Ag + , Al 3+ , Au 3+ , Ca 2+ , Cd 2+ ,Co 2+ , Cr 3+ , Cu 2+ , Fe 3+ , Hg 2+ , K + , Mg 2+ ,Mn 2+ , Na + , Ni 2+ , Pb 2+ , Pd 2+ , Pt 2+ , Zn 2+Add an equal amount of the above-mentioned probe solution in the solution of metal ions, adopt the fluorescence spectrometer to carry out the fluorescence spectrum analysis to the rhodamine-indole derivative that embodiment 1 makes, the fluorescence spectrum figure of gained is shown in image 3 . The rhodamine-indole derivatives prepared in Example 1 of the present invention interact with divalent palladium ions, and the emission peak at 590nm increases significantl...

Embodiment 3

[0034] The concentration is 5×10 -6 The rhodamine-indole derivatives of mol / L are added concentration respectively in the acetonitrile / water (volume ratio 9:1) solution of fluorescence probe as 0mol / L, 5×10 -7 mol / L, 1×10 -6 mol / L, 1.5×10 -6 mol / L, 2×10 -6 mol / L, 2.5×10 -6 mol / L, 3×10 -6 mol / L, 3.5×10 -6 mol / L, 4×10 -6 mol / L, 4.5×10 -6 mol / L, 5×10 - 6 mol / L, 7.5×10 -6 mol / L, 1×10 -5 mol / L, 1.25×10 -5 mol / L, 1.5×10 -5 The divalent palladium ion of mol / L adopts fluorescence spectrometer to carry out fluorescence spectrum analysis to it respectively, record the fluorescence intensity value at 410 and 590nm place, the fluorescence spectrum figure of gained is shown in Figure 4 . by attaching Figure 4 It can be seen that as the palladium ion concentration increases, the fluorescence intensity of the rhodamine-indole derivative fluorescent probe at 410nm gradually weakens, and the fluorescence intensity at 590nm gradually increases, and the absorption peak intensit...

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Abstract

The invention provides a fluorescent probe based on a rhodamine-indole derivative as well as a preparation method and application of the fluorescent probe, wherein the rhodamine-indole derivative has a chemical structural formula as the specification. The rhodamine-indole derivative can selectively acts on a bivalent palladium ion, a fluorescent light becomes from blue to orange, and the rhodamine-indole derivative has a ratiometric fluorescence effect, can be used for realizing naked eye discrimination and detection and is particularly used as the fluorescent probe applied to convenient detection of the parallelism ion in a cell.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to fluorescent probes based on rhodamine-indole derivatives, their preparation methods and applications. Background technique [0002] Palladium is an important catalyst and plays a very important role in the synthesis of fine chemicals. However, palladium ions in the body can interact with DNA, thiol-containing amino acids, proteins and vitamin B6, thereby causing diseases. In addition, palladium has also become an important metal pollutant due to the large amount of palladium ion used. In view of its importance to life and the environment, scientists have been working on the use of selective fluorescence and fluorescent sensing probes to realize the detection of palladium ions in biological and environmental systems. [0003] In recent years, molecular probe technology has become an important means to detect metal ion pollution due to its high sensitivity, simple operation, and ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 王元吴伟娜李慧军吴浩
Owner HENAN POLYTECHNIC UNIV
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