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Bis-Schiff-base-connected symmetrical phenanthroimidazole Fe<3+> fluorescent probe and preparation method thereof

A fluorescent probe, phenanthroimidazole technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as iron ion recognition interference, and achieve high selectivity and sensitive response

Inactive Publication Date: 2016-06-22
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention is to solve the existing Fe 3+ Fluorescent probes require organic solvents to recognize the environment, and other metals interfere with the recognition of iron ions. However, the symmetrical phenanthroimidazole Fe that provides double Schiff base links 3+ Fluorescent probe and preparation method thereof

Method used

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  • Bis-Schiff-base-connected symmetrical phenanthroimidazole Fe&lt;3+&gt; fluorescent probe and preparation method thereof
  • Bis-Schiff-base-connected symmetrical phenanthroimidazole Fe&lt;3+&gt; fluorescent probe and preparation method thereof
  • Bis-Schiff-base-connected symmetrical phenanthroimidazole Fe&lt;3+&gt; fluorescent probe and preparation method thereof

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specific Embodiment approach 1

[0026] Specific embodiment 1: Symmetrical phenanthroimidazole Fe linked by double Schiff bases in this embodiment 3+ The structural formula of the fluorescent probe is:

[0027]

specific Embodiment approach 2

[0028] Specific embodiment two: Symmetrical phenanthroimidazole Fe linked by double Schiff bases of specific embodiment one 3+ The preparation method of fluorescent probe is carried out according to the following steps:

[0029] One, the synthesis of intermediate compound I:

[0030] Add phenanthrenequinone, o-nitrobenzaldehyde, aniline, and ammonium acetate into the reactor at a molar ratio of 1:1.5:1.5:2, then add glacial acetic acid as a solvent, heat up to 80-110°C and stir for 6-12 hours, Cool to room temperature, add water to the reactor, adjust the pH value to 8-10 with 10% sodium hydroxide solution, filter with suction to obtain a yellow solid, dry it, recrystallize it with ethyl acetate, and filter with suction , drying to obtain intermediate compound I;

[0031] Two, the synthesis of intermediate compound II:

[0032] Take by weighing 2mmol intermediate compound I and 0.35g Raney nickel and join in the reactor, then add ethanol as solvent, pass into nitrogen prote...

specific Embodiment approach 3

[0035] Specific embodiment three: the difference between this embodiment and specific embodiment two is that the acidic medium described in the step three is concentrated sulfuric acid with a mass percentage concentration of 98%, concentrated hydrochloric acid with a mass percentage concentration of 36-37%, ice Acetic or formic acid. Others are the same as in the second embodiment.

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Abstract

The invention relates to an Fe<3+> fluorescent probe and a preparation method thereof, particularly a bis-Schiff-base-connected symmetrical phenanthroimidazole Fe<3+> fluorescent probe and a preparation method thereof. The invention aims to solve the technical problems that the existing Fe<3+> fluorescent probe needs an organic solvent identification environment and copper ions can interfere with the identification of iron ions. The structural formula of the bis-Schiff-base-connected symmetrical phenanthroimidazole Fe<3+> fluorescent probe is disclosed in the specification. The preparation method comprises the following steps: 1. synthesizing an intermediate compound I from phenanthrenequinone, o-nitrobenzaldehyde, aniline and ammonium acetate; 2. synthesizing an intermediate compound II from the intermediate compound I, Raney nickel and hydrazine hydrate; and 3. synthesizing the Fe<3+> fluorescent probe from the intermediate compound II and terephthalaldehyde under acidic conditions. The Fe<3+> fluorescent probe can selectively identify Fe<3+> in a water-phase system within the wide pH value range of 1-9; the response time is 2 minutes; and when being used for Fe<3+> inspection, the Fe<3+> fluorescent probe has the advantage of no interference, and is convenient and quick.

Description

technical field [0001] The present invention relates to a kind of Fe 3+ Fluorescent probes and methods for their preparation. Background technique [0002] Iron element plays a very important role in the metabolic process of living body cells, such as oxygen transport, participating in enzyme reactions, etc. Whether it is the lack of iron or excessive intake, it will cause the disorder of the life system, so the detection of iron ions is very important. Significance. In recent years, more and more scientific researchers have begun to study iron ion fluorescent probes. Chang Lin and others reported the recognition performance of 5-sulfosalicylic acid on ferric ions [Journal of Hubei University for Nationalities (Natural Science Edition, 2011, 29(1), 1-4)]. The study found that Fe 3+ It can selectively quench the fluorescence of 5-sulfosalicylic acid. In 2014, Organic Chemistry reported the recognition of iron ions by rhodamine-based fluorescent probes in aqueous solution...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D235/02G01N21/64
CPCC07D235/02C09K11/06C09K2211/1007C09K2211/1044G01N21/6428G01N2021/6432
Inventor 赵冰刘婷邓启刚王丽艳阚伟宋波
Owner QIQIHAR UNIVERSITY
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