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Amino acid Schiff base and its synthesis method and application
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A synthetic method and amino acid technology, which is applied in the preparation of imino compounds, chemical instruments and methods, fluorescence/phosphorescence, etc., can solve problems such as poor solubility, and achieve the effects of enhanced fluorescence intensity, good solubility, and strong coordination ability
Active Publication Date: 2019-01-04
HARBIN UNIV OF SCI & TECH
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[0006] The present invention aims to solve the problem of poor solubility in the organic phase of the existing salicylaldehyde amino acid Schiff base zinc complex, and provides amino acid Schiff base fluorescent probe compounds and their synthesis methods and applications
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specific Embodiment approach 1
[0053] Specific embodiment 1: The structural formula of the amino acid Schiff base fluorescent probe compound in this embodiment is as follows:
[0054]
[0055] where R 1 for CH 3 -, tert-octyl or α,α'-dimethyl-α-phenyl; R 2 for CH 3 -, C 6 h 5 -or
specific Embodiment approach 2
[0056] Specific embodiment two: the synthetic method of amino acid Schiff base of this embodiment comprises the following steps:
[0057] 1. Fuckers Alkylation Reaction:
[0058] After mixing the alkylphenol with the catalyst p-toluenesulfonic acid, slowly add α-methylstyrene dropwise, under the protection of nitrogen, heat and reflux, the temperature is maintained at 74-76°C, after the dropwise addition, add saturated Na 2 CO 3 , adjust the pH to be neutral, concentrate to remove petroleum ether, and collect fractions at 180-200°C by vacuum distillation to obtain intermediate product A;
[0059] Wherein the molar ratio of alkylphenol to catalyst p-toluenesulfonic acid is 1:0.1~1, and the molar weight of α-methylstyrene is 0.9~1 times of the molar weight of alkylphenol;
[0060] Two, formylation reaction:
[0061] After mixing the intermediate product A prepared in step 1 with urotropine, add a certain amount of glacial acetic acid (as a reaction solvent), heat to reflux, a...
specific Embodiment approach 3
[0065] Specific embodiment 3: The difference between this embodiment and specific embodiment 2 is that the alkylphenol in step 1 is p-cresol, p-tert-octylphenol or 4-α, α'-dimethyl-α-phenyl phenol. Others are the same as in the second embodiment.
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Abstract
The invention discloses an amino-acid schiff base, and a synthesis method and an application thereof, relates to an amino-acid schiff base compound and a synthesis method and application thereof and mainly aims at solving the problem of poor organic phase solubility of an existing salicylaldehyde-amino acid schiff base compound. The invention relates to a structural formula of an amino-acid schiff base fluorescent probe compound. The synthesis method comprises the steps of (1) FriedelCrafts alkylation reaction; (2) formylation reaction; and (3) condensation reaction. The invention further discloses an application of the amino-acid schiff base in qualitative and quantitative analysis of trace metal ions Zn<2+> as a fluorescent probe. A hydrophobic group is introduced into a benzene ring of salicylaldehyde and is subjected to condensation reaction with amino acid to generate the amino-acid schiff base, and a complex generated through coordination of the amino-acid schiff base and zinc ions has good solubility in an organic phase and a fluorescent detection signal is obviously strengthened. The amino-acid schiff base can be applied to the field of the fluorescent probe.
Description
technical field [0001] The invention relates to an amino acid Schiff base compound and its synthesis method and application. Background technique [0002] Zinc ion is an important trace element in the human body, its content is second only to iron and ranks second among all trace elements. In addition, zinc is also widely used in many fields such as alloy manufacturing, battery production, compound fertilizer, and foliar fertilizer in industrial and agricultural production processes. Because of its important role in industrial and agricultural production, zinc also enters the environment along with various industrial processes and products, becoming a common pollutant. Therefore, the analysis and detection of zinc ions, especially the detection of zinc ions in life samples, has always been the focus of attention. [0003] The salicylaldehyde amino acid Schiff base is a class of organic ligands with a wide range of uses. Since Eichhorn et al first synthesized the Cu(II) co...
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