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Water-soluble copper ion fluorescent probe material based on naphthalimide dicarboxylic acid as well as preparation and application thereof

A technology of naphthalimide dicarboxylic acid and fluorescent probes, applied in the field of polymer materials and analytical chemistry, can solve the problems of complex synthesis, limited application prospects, poor water solubility of fluorescent probes, etc., achieve high detection sensitivity, improve production The effect of rate and purity

Inactive Publication Date: 2017-12-22
LANZHOU JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the poor water solubility and complex synthesis of these fluorescent probes limit their application prospects.

Method used

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  • Water-soluble copper ion fluorescent probe material based on naphthalimide dicarboxylic acid as well as preparation and application thereof
  • Water-soluble copper ion fluorescent probe material based on naphthalimide dicarboxylic acid as well as preparation and application thereof
  • Water-soluble copper ion fluorescent probe material based on naphthalimide dicarboxylic acid as well as preparation and application thereof

Examples

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Embodiment Construction

[0041] The preparation of the probe WP of the present invention and the fluorescence recognition method and application of copper ions will be described in detail below through specific implementation.

[0042] 1. Preparation of probe WP:

[0043] (1) N - Synthesis of n-butyl-4-bromo-1,8-naphthalimide: Weigh 15g (0.054mol) 4-bromo-1,8-naphthalene anhydride and 7.9g (0.108mol) n-butylamine, add to Into a 500mL round bottom flask, add 300mL of absolute ethanol to mix evenly, stir and heat up to 80°C, and reflux for 3 hours; after the reaction is completed, cool the resulting light yellow mixture to room temperature, suction filter, and wash with absolute ethanol for 3 times , put into the oven to dry for 24h, get N -n-butyl-4-bromo-1,8-naphthalimide, 17.0 g, yield 94.5%. mp:107-109℃.R f =0.75 (CH 2 Cl 2 ). Elem. Anal. calcd. C 57.85; H 4.25; N 4.22 %; found: C 57.79;

[0044] (2) N -Synthesis of n-butyl-4-ethylenediamine-1,8-naphthalimide: Weigh 12.2g (201.67mmol) of eth...

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Abstract

The invention discloses a water-soluble copper ion fluorescent probe and a preparation method thereof and belongs to the technical field of chemical synthesis and analytical chemistry. The chemical name of the water-soluble copper ion fluorescent probe disclosed by the invention is N-n-butyl-4-[ethylenediamine-2-N,N'-di(3-propionic acid)]-1,8-naphthalimide; a synthesis method of the water-soluble copper ion fluorescent probe comprises the following steps: firstly, carrying out amidation on 4-bromo-1,8-naphthalic anhydride and n-butylamine; replacing 4-site bromine with ethylenediamine; then carrying out Michael reaction on a product of the last step and methyl acrylate; finally, carrying out alkaline hydrolysis and treating through a cation exchange column to obtain the copper ion fluorescent probe. An experiment shows that the probe can be used for selectively detecting copper ions and has fluorescent quenching in a DMSO / HEPES (Dimethyl Sulfoxide / 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) buffering system; the copper ions are quantitatively detected; the water-soluble copper ion fluorescent probe has high detection sensitivity and the identification is not interfered by other ions, so that the copper ion fluorescent probe can be used for detecting heavy metal ions and is especially used for detecting the copper ions in biological tissues and environment sewage.

Description

technical field [0001] The invention relates to a water-soluble copper ion fluorescent probe material, in particular to a water-soluble copper ion fluorescent probe material based on naphthalimide dicarboxylic acid and a preparation method thereof; the present invention also relates to the copper ion fluorescent probe material The invention relates to the application of highly selective fluorescent recognition of copper ions, belonging to the technical field of polymer materials and the technical field of analytical chemistry. Background technique [0002] Copper is the third most essential trace element after iron and zinc in the human body. It participates in many basic physiological processes in the human body, such as protein function and structural strengthening, gene expression, and nervous system. It is well known that copper acts as a catalytic factor for a large number of metalloenzymes in living organisms, but excessive intake of copper can cause some neurological ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643G01N2021/6439
Inventor 吴辉禄汤霞范旭阳陈英李创
Owner LANZHOU JIAOTONG UNIV
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