Photosensitive chromatographic stationary phase based on silicon substrate modified by azobenzene photosensitive compound

A photosensitive compound and chromatographic stationary phase technology, applied in the field of photosensitive chromatographic stationary phase, can solve the problems of non-in-situ regulation and single property of chromatographic stationary phase, etc.

Inactive Publication Date: 2019-10-18
YANBIAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the problem that the existing chromatographic stationary phase has a single property and cannot be regulated

Method used

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  • Photosensitive chromatographic stationary phase based on silicon substrate modified by azobenzene photosensitive compound
  • Photosensitive chromatographic stationary phase based on silicon substrate modified by azobenzene photosensitive compound
  • Photosensitive chromatographic stationary phase based on silicon substrate modified by azobenzene photosensitive compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 The method for synthesizing silylated photosensitive compound with 4-hydroxyazophenol as raw material

[0036] Dissolve 0.99 g (0.005 mol) of 4-hydroxyazophenol in 12.5 mL of N,N-dimethylformamide, 0.90 g (0.0225 mol) of sodium hydride in 15 mL of N,N-dimethylformamide, and The above two solutions were mixed in a 100 mL round bottom flask, stirred at room temperature for 2 h; 1.82 g (0.015 mol) allyl bromide was added to the above mixed solution, and the reaction temperature was 60 o C, stirred for 24 h; after the reaction was completed, it was extracted with ethyl acetate, washed repeatedly with cold water, and dried at room temperature to obtain an orange-red crude solid product; the crude solid product was dissolved in a small amount of ethanol and crystallized at low temperature to obtain an orange-red fixed product 4 - Allyloxyazobenzene ( figure 1 , response(1));

[0037] 4-allyloxyazobenzene (201 mg, 0.001 mol), triethoxysilane (746 mL, 0.005 mol) ...

Embodiment 2

[0038] Example 2 Using 4-dimethylamino-4'-hydroxyazobenzene as a raw material for the synthesis of silylated photosensitive compounds

[0039]Dissolve 1.21 g (0.005 mol) of 4-dimethylamino-4'-hydroxyazobenzene in 20 mL of N,N-dimethylformamide, and 0.90 g (0.0225 mol) of sodium hydride in 15 mL of N,N- Dimethylformamide, mix the above two solutions in a 100 mL round bottom flask, stir at room temperature for 2 h; add 1.82 g (0.015 mol) allyl bromide to the above mixture, and react under nitrogen atmosphere temperature 80 o C, stirred for 24 h; after the reaction was completed, it was extracted with ethyl acetate, washed repeatedly with cold water, and dried at room temperature to obtain the crude solid product; the crude solid product was dissolved in a small amount of ethanol and crystallized at low temperature to obtain the intermediate product 4-dimethylamino -4'-allyloxyazobenzene ( figure 2 , response(1));

[0040] 4-Dimethylamino-4'-allyloxyazobenzene (241 mg, 0.001 ...

Embodiment 3

[0041] Example 3 Preparation method of 4-[3-(triethoxysilyl)propoxy]azobenzene photosensitive thin-layer chromatography stationary phase

[0042] Dip silica gel (5 g) into freshly prepared piranha solution (30% H 2 o 2 : 98%H 2 SO 4 =3:7), hydroxylation for 3 h, stirring and dispersing washing with ultrapure water, natural sedimentation, removing the supernatant, repeating the steps of washing and separation until the supernatant is neutral, and vacuum drying at 60°C to obtain hydroxylated silica gel ; Subsequently, 1 g of hydroxylated silica gel was dispersed in 20 mL of toluene, 40 μL of 4-[3-(triethoxysilyl) propoxy]azobenzene was added to the dispersion, and the reaction was refluxed at 80 °C for 16 h. At the end, the product was washed with toluene until the upper layer was colorless, and dried overnight at 80°C in vacuum to obtain a photosensitive thin-layer chromatography stationary phase named 4-[3-(triethoxysilyl)propoxy]azobenzene Photosensitive TLC stationary ph...

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Abstract

The invention discloses a photosensitive chromatographic stationary phase based on silicon substrate modified by an azobenzene photosensitive compound. The azobenzene photosensitive compound, sodium hydride and allyl bromide are added into N,N-dimethylformamide for reaction for 12-24 hours at 60-80 DEG C; extraction and crystallization at low temperature are carried out to obtain an intermediate product; the intermediate product, triethoxysilane and platinum (0)-1,3- divinyl-1,1,3,3-tetramethyldisiloxane are added to toluene for reaction at 70-80 DEG C for 12-24 hours; after the reaction, a solvent is removed, separation and purification are carried out, and the silanized azobenzene photosensitive compound is obtained; the silanized azobenzene photosensitive compound with a weight ratio of(1-2):25 and the silicon substrate with hydroxyl on the surface of the silicon substrate are added into toluene for reaction at 60-80 DEG C for 12-24 hours; and centrifugation, washing and drying arecarried out to obtain the photosensitive chromatographic stationary phase. The photosensitive chromatographic stationary phase has the beneficial effects that reversible adjustment and control in situ can be achieved; and the preparation method is simple, the operation is easy, the cost is low, and universality is achieved.

Description

technical field [0001] The invention belongs to the technical field of photosensitive chromatographic stationary phase materials, in particular to a photosensitive chromatographic stationary phase based on azobenzene photosensitive compound modified silicon base. Background technique [0002] Chromatographic separation is mainly based on the difference in the distribution coefficient of the target substance in the stationary phase and the mobile phase, and is repeatedly distributed between the two phases to achieve the purpose of separation. Therefore, selecting a stationary phase with a suitable polarity according to the physical and chemical properties of the substances to be separated is one of the keys to achieve efficient separation of the target substances. At present, commercial chromatographic columns (gas-phase capillary columns, liquid-phase chromatographic columns, etc.) have a single stationary phase, and the polarity cannot be adjusted in situ. Therefore, when s...

Claims

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Application Information

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IPC IPC(8): B01J20/286B01J20/30B01D15/08G01N30/92
CPCB01D15/08B01J20/286G01N30/92
Inventor 李东浩吴立新李鑫琦商海波
Owner YANBIAN UNIV
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