Ortho-aminophenol Schiff base, and synthesis method and application thereof
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A technology of o-aminophenol and a synthesis method, applied in the field of o-aminophenol Schiff base compounds and their synthesis, can solve problems such as poor solubility, and achieve the effects of enhanced fluorescence intensity, good solubility, and increased solubility
Active Publication Date: 2017-11-07
HARBIN UNIV OF SCI & TECH
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[0005] The present invention aims to solve the problem of poor solubility in the organic phase of the existing salicylaldeh
Method used
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specific Embodiment approach 1
[0049] Specific embodiment one: the structural formula of o-aminophenol Schiff base in this embodiment is as follows:
[0050]
[0051] where R is CH 3 -, tert-octyl or α,α'-dimethyl-α-phenyl.
specific Embodiment approach 2
[0052] Specific embodiment two: the synthetic method of o-aminophenol Schiff base of the present embodiment comprises the following steps:
[0053] 1. Fuckers Alkylation Reaction:
[0054] After mixing the alkylphenol and the catalyst p-toluenesulfonic acid, add α-methylstyrene dropwise, under the protection of nitrogen, heat and reflux, and keep the temperature at 74-76°C. After the dropwise addition, add saturated Na 2 CO3 , 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;
[0055] 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;
[0056] Two, formylation reaction:
[0057] After mixing the intermediate product A prepared in step 1 with urotropine, add glacial acetic acid and heat to reflux. When the temperature reaches 120-140°C, keep th...
specific Embodiment approach 3
[0061] 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 ortho-aminophenol Schiff base, and a synthesis method and application thereof, and relates to an ortho-aminophenol Schiff base compound, and a synthesis method and application thereof. The invention aims to solve the problem of poor organic phase solubility of a conventional salicylaldehyde ortho-aminophenol Schiff base zinc complex. The invention relates to a structural formula of an ortho-aminophenol Schiff base fluorescent probe compound. The synthesis method comprises: 1, FriedelCrafts alkylation; 2, formylation reaction; 3, condensation reaction. The ortho-aminophenol Schiff base serving as a fluorescent probe is applied to qualitative and quantitative analysis for a trace metal ion Zn2+. After a lipophilic group is introduced to a benzene ring of salicylaldehyde, the condensation reaction with ortho-aminophenol is performed to generate the ortho-aminophenol Schiff base, and a complex generated by coordination between the ortho-aminophenol Schiff base and a zinc ion presents good solubility in an organic phase, and a fluorescence detection signal is obviously enhanced. The invention can be applied to the field of fluorescent probes.
Description
technical field [0001] The invention relates to an o-aminophenol Schiff base compound and a synthesis method and application thereof. 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. When an organism takes in too much or not enough zinc ions, it will lead to metabolic disorders of the body, and severe cases can be life-threatening. 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. ...
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