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Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof

A technology of naphthalimide ethyl and fluorescent reagent, which is applied in the field of tris[4--1,8-naphthalimide ethyl]amine fluorescent reagent, can solve problems such as toxicity and achieve high yield High, simple separation method, enhance the effect of coordination and identification ability

Active Publication Date: 2014-08-20
广西平果润民脱贫发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, aluminum ions are very toxic to the human central nervous system

Method used

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  • Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof
  • Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof
  • Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] (1) Synthesis of intermediate raw material 4-(4-morpholinyl)-1,8-naphthalic anhydride

[0061] N 2 Under protection, in a 250mL round bottom flask, add 4-bromo-1,8-naphthalene dicarboxylic anhydride (8g, 28.87 mmol), ethylene glycol methyl ether 100 mL, CuI (500mg, 2.625 mmol), and then add morphine Phenyl (7.55g, 86.62 mmol), stirred at reflux for 7h, filtered with ethanol, then filtered with chloroform, distilled off the solvent under reduced pressure, and separated the crude product by column chromatography (eluent: ethyl acetate / petroleum ether, v / v, 5 / 2) 5.91 g of the yellow product was obtained, with a yield of 72.3%.

[0062] (2) Synthesis of compound a, tris[4-(4-morpholinyl)-1,8-naphthalimide ethyl]amine

[0063] N 2 Under protection, add 4-(4-morpholinyl)-1,8-naphthalene dicarboxylic anhydride (2.32g, 8.208 mmol) and 150mL ethanol into a 250mL three-necked flask. After dissolving, add triaminoethylamine (400mg, 2.736 mmol), heated to reflux for 5h. The s...

Embodiment 2

[0065] Add the N,N-dimethylamide stock solution of compound a (1.00×10 -4 mol L -1 , 1mL), metal ion Al 3+ or Cr 3+ (2.00×10 -3 mol L -1 , 1 mL). Use N,N-dimethylformamide, aqueous solution and Tris-HCl mixture to make the final solvent of the solution system be N,N-dimethylformamide / water / Tris-HCl (v / v, 3 / 2, pH 6) Dilute to the mark, shake well, transfer to a 1cm quartz cuvette for fluorescence spectrum or UV-visible absorption spectrum measurement.

[0066] The reagents used are analytical reagents, and the test water is double distilled water.

[0067] The model of the fluorescence spectrophotometer used is Cary Eclipse fluorescence spectrophotometer, manufactured by VARIAN Company of the United States. The ultraviolet-visible spectrophotometer model is UV-vis TU-1901, manufactured by Beijing General Instrument Co., Ltd.

[0068] In N,N-dimethylformamide / water / Tris-HCl (v / v, 3 / 2, pH 6) solution, compound a itself has a strong fluorescence emission with an excitat...

Embodiment 3

[0076] (a) Determination of trace amounts of Al in synthetic water samples by the calibration curve method of the fluorescence spectrum of compound a 3+ .

[0077] 1. Take several 10.0ml volumetric flasks, and add 100 μmol L -1 1ml of compound a in N,N-dimethylformamide.

[0078] 2. Add different concentrations of Al to each volumetric flask in turn 3+ For the standard solution, use N,N-dimethylformamide / water / Tris-HCl (v / v, 3 / 2, pH 6) mixed solution to make up to 10.0ml, shake well.

[0079] 3. Add sample solution to one of the volumetric flasks, use N,N-dimethylformamide / water / Tris-HCl (v / v, 3 / 2, pH 6) mixture to make up to 10.0ml, shake well .

[0080] 3. The fluorescence intensity was measured on a fluorescence spectrophotometer with 385nm as the excitation wavelength and 548nm as the emission wavelength, and was measured 3 times in parallel.

[0081] 4. The fluorescence intensity was plotted against the standard Al 3+ Concentration calibration curve (attached ...

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Abstract

The invention discloses tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof, and belongs to the technical field of organic synthesis and analytical chemistry. Tris-amino ethyl amine is used as a structure platform to react with 4-(4-morpholine)-1, 8-naphthalic acid anhydride to obtain the compound a with a chemical name of tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine, and three side chains of the compound are connected with fluorophores. Reaction raw materials are easily obtained, the synthesis method is simple, and the target product can be obtained by the two steps of reaction. In N, N-dimethyl formamide / water (V / V, 3 / 2), tris (hydroxymethyl) aminomethane-hydrochloric acid (Tris-HCl, pH6) buffer solution mixed solvent, the compound a can be used as a fluorescent or colorimetric reagent for detection of trace Al <3 + > and Cr <3 + >. The structure formula of the compound a is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, in particular to a tris[4-(4-morpholinyl)-1,8-naphthalimide ethyl]amine fluorescent reagent and its preparation and application. Background technique [0002] In recent decades, in the fields of industry, agriculture, medicine, food science, environmental chemistry, pharmacology, physiology, molecular biology, cell biology, molecular genetics and other fields, fluorescent probes, as an important detection technology, have been widely used. widely used. Especially based on the important role of heavy metals and transition metal ions in environmental science and life science research, the design and synthesis of fluorescent probe molecules with novel structures, better selectivity and sensitivity, and specific metal ions as recognition objects have application prospects. [0003] The tripod structure compound centered on macrocycle, carbon atom and nitrogen atom has three ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/14G01N21/64G01N21/33G01N21/31
Inventor 沈韵曾晞牟兰李丽
Owner 广西平果润民脱贫发展有限公司
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