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Binol-diform condensed o-aminophenol Schiff base and its synthesis method and application
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A technology of ortho-aminophenol and Schiff base, which is applied in the field of Binol-diform condensed o-aminophenol Schiff base and its synthesis and application, can solve the problem that Schiff base has no ability to recognize metals, and achieve enhanced fluorescence recognition ability , the effect of excellent fluorescent performance
Active Publication Date: 2019-08-20
HARBIN UNIV OF SCI & TECH
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[0005] The present invention aims to solve the problem that the Schiff bases obtained from planar structure 2-hydroxyl-1-naphthaldehyde adeno-aminophenol have no ability to recognize metals, and provide Binol-diform adeno-aminophenol Schiff bases and their synthesis methods and applications
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specific Embodiment approach 1
[0036] Specific embodiment 1: In this embodiment, the structural formula of the Binol-diform condensed o-aminophenol Schiff base fluorescent probe compound is as follows:
[0037]
[0038] where R is -H or -NO 2 .
specific Embodiment approach 2
[0039] Specific embodiment two: the synthesis method of Binol-diform adeno-aminophenol Schiff base of this embodiment, the steps are as follows:
[0040] 1. Dissolve o-aminophenols in an organic solvent, then add Binol-diform, and heat for 1 to 2 hours to obtain a red liquid, namely 2,2'-dihydroxy-1,1'-binaphthyl-3,3 Crude product of '-diformaldehyde-condensed o-aminophenol Schiff base;
[0041] 2. Concentrate the crude product of 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarbaldehyde adeno-aminophenol Schiff base, dissolve it in methanol, filter it with suction, and wash it to obtain a red solid. Vacuum drying, the obtained pure product is 2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dimethylaldehyde adeno-aminophenol Schiff base; wherein in step 1, Binol-diform and o-amino The molar ratio of phenol is 1:2~3.
[0042] The Binol-diform described in Step 1 is 2,2'-dihydroxy-1,1'-bi-3,3'-dinaphthaldehyde.
specific Embodiment approach 3
[0043] Embodiment 3: This embodiment is different from Embodiment 2 in that: in the preparation step 1, the o-aminophenol is o-aminophenol or 2-amino-5-nitrophenol. Others are the same as in the second embodiment.
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Abstract
The invention provides Binol-diform-o-aminophenol type Schiff base, and a synthesis method and an application thereof, and relates to a 2,2'-dihydroxy-1,1'-dinaphthalene-3,3'-diformaldehyde-o-aminophenol type Schiff base, and a synthesis method and an application thereof. The invention aims to solve a problem that Schiff base prepared from 2-hydroxy-1-naphthaldehyde-o-aminophenol in a plane structure has no recognition capability on metals. The structure formula of the 2,2'-dihydroxy-1,1'-dinaphthalene-3,3'-diformaldehyde-o-aminophenol type Schiff base is represented as the description. The method includes the steps of: 1) preparing a crude product of the 2,2'-dihydroxy-1,1'-dinaphthalene-3,3'-diformaldehyde-o-aminophenol type Schiff base; and 2) concentrating the crude product, dissolvingthe crude product in methanol, performing suction filtration, and washing and drying the product to obtain a pure product. Compared with analogues having plane structures, the synthesized Schiff basehas significantly enhanced fluorescent recognition capability. The compound can be used for detecting cerium ions in trace amount.
Description
technical field [0001] The invention relates to a 2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dimethylaldehyde adeno-aminophenol Schiff base, a synthesis method and an application thereof. Background technique [0002] Rare earth elements are valuable strategic resources, and my country's reserves rank first in the world. In recent years, as the demand for rare earths has increased year by year, a large number of rare earth minerals have been mined, which has led to more and more rare earth elements migrating to the environment, causing serious ecological damage and environmental pollution, degrading cultivated land, reducing food production and even extinction. Produce. In addition, studies have shown that long-term low-dose intake of rare earth metals can damage the brain, liver, bone, endocrine and immune functions. Cerium (Ce) is the rare earth metal with the highest content in the earth's crust, and its qualitative and quantitative detection is of great significance. [0003...
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