CN110142036A - A kind of preparation and application of glucose quantum dot bonded silica gel hydrophilic chromatographic stationary phase - Google Patents

A kind of preparation and application of glucose quantum dot bonded silica gel hydrophilic chromatographic stationary phase Download PDF

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Publication number
CN110142036A
CN110142036A CN201910454808.XA CN201910454808A CN110142036A CN 110142036 A CN110142036 A CN 110142036A CN 201910454808 A CN201910454808 A CN 201910454808A CN 110142036 A CN110142036 A CN 110142036A
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glucose
quantum dot
silica gel
bonded silica
preparation
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CN110142036B (en
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邱洪灯
远宁
陈佳
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Lanzhou Institute of Chemical Physics LICP of CAS
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

The invention discloses a kind of preparation methods of glucose quantum dot bonded silica gel chromatograph packing material; it is to be uniformly mixed silica gel and r- isocyanatosilanes coupling agent in benzene kind solvent; nitrogen or argon atmosphere protection; 12 ~ 48h is stirred to react at 60 ~ 150 DEG C; it is dispersed again in organic solvent after reaction product organic solvent washing; then glucose quantum dot function monomer and catalyst triethylene diamine, N is added2Atmosphere, in 60 ~ 150 DEG C of 12 ~ 48 h of reaction；Organic solvent and water washing are used after reaction, and centrifugation is dry to get glucose quantum dot bonded silica gel chromatograph packing material.Chromatographic isolation experiment shows that chromatograph packing material prepared by the present invention is hydrophilic chromatographic stationary phase, has good separation effect for base nucleosides, carbohydrate.

Description

A kind of preparation and application of glucose quantum dot bonded silica gel hydrophilic chromatographic stationary phase
Technical field
The present invention relates to a kind of preparations of glucose quantum dot bonded silica gel hydrophilic chromatographic filler, are mainly used for base core The separation of glycosides, carbohydrate belongs to chromatographic stationary phases technical field.
Background technique
Silica gel main component is silica, and silicon dioxide microsphere is since shape is uniform, size is controllable, the easy functionalization in surface The features such as, there is great application value in chromatograph packing material.Quantum dot due to partial size is small, with big specific surface area/volume Than, be conducive to mass transfer, designability is strong, functional group is abundant, it is easily prepared and modify the advantages that, modification and modification for material.
The surface of glucose quantum dot is rich in hydroxyl, is easy to functionalization, and silica gel bonded glucose quantum dot is as hydrophilic color Stationary phase is composed, the excellent chromatographic performance of quantum dot can be given full play to, not only can solve tailing problem, improves column effect, but also Opposed polarity stationary phase can be prepared by the way that surface is modified, improve separation selectivity.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of glucose quantum dot silica gel chromatographic column filling material；
It is another object of the present invention to the chromatographic separation performances to above-mentioned glucose quantum dot silica gel chromatographic column filling material to study.
One, the preparation of glucose quantum dot silica gel chromatographic column filling material
Silica gel and r- isocyanatosilanes coupling agent are uniformly mixed in benzene kind solvent, nitrogen or argon atmosphere protection, 60 ~ It is stirred to react 12 ~ 48h at 150 DEG C, is dispersed again in organic solvent after reaction product organic solvent washing, function is then added Energy monomeric glucose quantum dot and catalyst triethylene diamine, N2Atmosphere, in 60 ~ 150 DEG C of 12 ~ 48 h of reaction；After reaction With organic solvent and water washing, centrifugation, the dry silica gel chromatographic column filling material modified to get glucose quantum dot.
The preparation of glucose quantum dot is with reference to the documents such as Yang, Chem Commun, and 2011,47,11615-11617.
The structure of the r- isocyanatosilanes coupling agent are as follows: X3Si(CH2)mNCO, wherein X is methoxy or ethoxy, m=3 ~8；The mass ratio of silica gel and r- isocyanatosilanes coupling agent is 1:1 ~ 4:1.The bonded amount of glucose quantum dot is by strictly controlling The ingredient proportion of silica gel and silane coupling agent processed controls.
The mass ratio of silica gel and glucose quantum dot is 4:1 ~ 24:1.
The addition of catalyst triethylene diamine (DABCO) is the 1 ~ 5% of glucose quantum dot function monomer quality.
The benzene kind solvent is benzene,toluene,xylene；Organic solvent is DMF, acetonitrile, tetrahydrofuran.
Two, the structure and performance of glucose quantum dot silica gel chromatographic column filling material
1, elemental analysis
Table 1 is the elemental analysis of glucose quantum dot bonded silica gel chromatograph packing material.Elemental analysis the results show that include naked silica gel, Glucose quantum dot, silica gel bonded glucose quantum dot (Sil-glc-CDs), silica gel bonded silane coupling agent and silica gel bonded Portugal Five kinds of grape glycan molecule (Sil-glc).The C% of Sil-glc-CDs, H% content are obviously increased than the content of naked silica gel, illustrate CDs at Function is bonded to Silica Surface.
。
2, infrared spectrum analysis (FT-IR)
Fig. 1 is infrared spectroscopy (FT-IR) figure of glucose quantum dot bonded silica gel chromatograph packing material.In FT-IR spectrum, it was confirmed that Glucose Carbon is melted into C point under hydrothermal condition, and the surface CDs has hydrophilic functional group's generation to compare with the infrared spectrum of glucose, such as In 1603 cm-1With 3437 cm-1There is strong absorption peak at place, illustrates the presence for having C=O He-OH.In addition, C-O-C symmetrical and Asymmetric stretching vibration peak is respectively in 1263 cm-1With 1069 cm-1There is absorption at place, this is that hydro-thermal reaction aoxidizes part CDs As a result.And in the infrared spectrum of Sil-glc-CDs, 1654 cm-1Represent the characteristic peak of C=O in carbamate, 1550 cm-1 It is then the stretching vibration peak of secondary amine, 1095 cm-1Strong absorb the flexible vibration for being attributable to Si-O on silica gel or silane reagent It is dynamic.These characteristic absorption peaks further illustrate that quantum dot is successfully bonded in Silica Surface.
3, tem study (TEM)
Fig. 2 is transmission electron microscope (TEM) figure of glucose quantum dot bonded silica gel chromatographic stationary phases.TEM characterization includes naked silica gel, silicon Glue is bonded glucose quantum dot (Sil-glc-CDs), silica gel bonded glucose molecule (Sil-glc).It can be observed from Fig. 2, silicon It is about 65 nm that glue, which is bonded the surface even application of glucose quantum dot (Sil-glc-CDs) CDs, thickness,.And Sil-glc is solid Determining phase surface then can't see CDs.
4, hydrophily judges chromatogram
In 94 % acetonitriles, 100 mM, 6% ammonium acetate, 25 DEG C of column temperature, 254 nm of pH of buffer=7.0, UV detector, 1 ml/ of flow velocity Three kinds of separation of methylbenzene, cytimidine, uracil substances are separated under the chromatographic condition of min.Fig. 3 is glucose quantum dot bonded silica Glue chromatographic stationary phases hydrophily chromatographic fractionation figure.In Fig. 3, peak sequence is toluene, uracil, cytimidine, illustrates Sil- Glc-CDs stationary phase is hydrophilic chromatographic stationary phase.
4, the separation chromatogram of base nucleosides
Chromatographic condition: in 94 % acetonitriles, 100 mM, 6 % ammonium acetate, 25 DEG C of column temperature, pH of buffer=7.0, UV detector (UV) 254 nm, 1 mL/min of flow velocity.
Fig. 4 is separation chromatogram of the glucose quantum dot bonded silica gel chromatographic stationary phases to 9 kinds of base nucleosides.Fig. 4 shows, Sil-glc-CDs is to thymidine, thymidine, uridine, adenosine, adenine, cytimidine (inosine), cytimidine core 9 kinds of glycosides, guanosine and xanthosine base nucleosides have good separation effect.
5, sugared separation chromatogram
Chromatographic condition: 94 % acetonitriles, 100 mM, 6 % ammonium acetate, 25 DEG C of column temperature, photodetector is evaporated in pH of buffer=7.0 (ELSD) 254 nm, 1 mL/min of flow velocity.
Fig. 5 is glucose quantum dot bonded silica gel chromatographic stationary phases to 6 kinds of sugared separation chromatograms.Fig. 5 shows, Sil- Glc-CDs stationary phase has carbohydrate (including six kinds of deoxyribose, ribose, xylose, fructose, dextrose and saccharose carbohydrates) good Good separating effect.
6, the separation of fructus lycii actual sample
Chromatographic condition: in 94 % acetonitriles, 100 mM, 6 % ammonium acetate, 25 DEG C of column temperature, photodetector is evaporated in pH of buffer=7.0 (ELSD) 254 nm, 1 mL/min of flow velocity.
Fig. 6 is separation chromatogram of the glucose quantum dot bonded silica gel chromatographic stationary phases to fructus lycii actual sample.It can see Out, in fructus lycii actual sample fructose and glucose have good separation effect.
In conclusion the stationary phase preparation process is simple and reliable, raw material is easy to get, it is easy to accomplish batch production.In addition, this is solid Fixed is mutually the hydrophilic pattern chromatographic stationary phases with universality, has good separation performance to most of polar compounds, is had good Good market application prospect.
Detailed description of the invention
Fig. 1 is infrared spectroscopy (FT-IR) figure of glucose quantum dot bonded silica gel chromatographic stationary phases.
Fig. 2 is transmission electron microscope (TEM) figure of glucose quantum dot bonded silica gel chromatographic stationary phases.
Fig. 3 is glucose quantum dot bonded silica gel chromatographic stationary phases hydrophily chromatographic fractionation figure.
Fig. 4 is separation chromatogram of the glucose quantum dot bonded silica gel chromatographic stationary phases to 9 kinds of base nucleosides.
Fig. 5 is glucose quantum dot bonded silica gel chromatographic stationary phases to 6 kinds of sugared separation chromatograms.
Fig. 6 is separation chromatogram of the glucose quantum dot bonded silica gel chromatographic stationary phases to fructus lycii actual sample.
Specific embodiment
It is done below by preparation method of the specific embodiment to glucose quantum dot bonded silica gel chromatographic stationary phases of the present invention It further illustrates.
Embodiment 1
2.5 g silica gel ultrasonic disperses are accurately weighed in 30 ml anhydrous toluene solutions, be added 6 mmol(1.5 g) r- isocyanide Sour propyl trimethoxy silicane, N2In 100 DEG C of 48 h of reaction under atmosphere.Product dry toluene after reaction, anhydrous DMF respectively wash one Time, then be dispersed in 30 ml anhydrous DMFs, 200mg glucose quantum dot, 0.3 mmol(6.6 mg be added) DABCO, N2Under atmosphere, in 120 DEG C of 24 h of reaction；Then with toluene, water, ethanol washing centrifugation, it is finally placed in drying in 80 DEG C of baking ovens, is obtained To glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum dot bonded amount of the stationary phase is good, and separating effect is good It is good.
Embodiment 2
3 g silica gel ultrasonic disperses are accurately weighed in 20 ml anhydrous toluene solutions, be added 6 mmol(1.5 g) r- isocyanic acid Propyl-triethoxysilicane, in 120 DEG C of N224 h are reacted under atmosphere.Product dry toluene after reaction, anhydrous DMF are respectively washed One time.Be dispersed in 20 ml anhydrous DMFs again, be added 250mg glucose quantum dot, 0.3 mmol(6.6 mg) DABCO It is catalyst, N2Under atmosphere, after 120 DEG C of 24 h of reaction, it is centrifuged with anhydrous DMF, water, ethanol washing, is finally placed in 60 DEG C of bakings It is dry in case, obtain glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum dot bonded amount of the stationary phase is optimal, Separating effect is optimal.
Embodiment 3
2 g silica gel ultrasonic disperses are accurately weighed in 30 ml anhydrous dimethyl benzole solns, be added 3 mmol(0.75 g) r- isocyanide Acid butyl trimethoxy silane, in 80 DEG C of N248 h are reacted under atmosphere.Product dry toluene after reaction, anhydrous acetonitrile are each It washes one time；It is dispersed in 20 ml anhydrous acetonitriles again, 500 mg glucose quantum dots, 0.25 mmol(5.5 mg is added) DABCO, N2Under atmosphere, after 80 DEG C of 48 h of reaction, it is centrifuged, is finally placed in 50 DEG C of baking ovens with anhydrous DMF, water, ethanol washing It is dry, obtain glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum dot bonded amount of the stationary phase is good, separation It works well, but relatively weaker compared with embodiment 2.
Embodiment 4
1.5 g silica gel ultrasonic disperses are accurately weighed in 40 ml anhydrous toluene solutions, be added 1 mmol(0.25 g) r- isocyanide Sour hexyl trimethoxysilane, in 150 DEG C of N212 h are reacted under atmosphere.Product dry toluene after reaction, anhydrous tetrahydro furan It mutters and respectively washes one time.It is dispersed in 40 ml anhydrous tetrahydro furans again, 500 mg glucose quantum dots, 0.2 mmol is added The DABCO of (4.4 mg), in 150 DEG C of N212 h are reacted under atmosphere, are centrifuged with anhydrous tetrahydro furan, water, ethanol washing, most It is placed on drying in 70 DEG C of baking ovens, obtains glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum of the stationary phase Point bonded amount is good, good separation, but relatively weaker compared with embodiment 2.
Embodiment 5
2 g silica gel ultrasonic disperses are accurately weighed in 50 ml anhydrous toluene solutions, be added 4 mmol(1 g) r- isocyanic acid fourth Ethyl triethoxy silicane alkane, in 90 DEG C of N224 h are reacted under atmosphere.Product anhydrous dimethyl benzene, anhydrous acetonitrile are respectively washed after reaction One time.It is dispersed in 50 ml anhydrous acetonitriles again, 300 mg glucose quantum dots, 0.25 mmol(5.5 mg is added) DABCO, in 90 DEG C of N248 h are reacted under atmosphere, are centrifuged with anhydrous acetonitrile, water, ethanol washing, are finally placed in 50 DEG C of baking ovens Interior drying obtains glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum dot bonded amount of the stationary phase is good, point From working well, but it is essentially identical compared with embodiment 3.
Embodiment 6
2.2 g silica gel ultrasonic disperses are accurately weighed in the anhydrous benzole soln of 25 ml, be added 2 mmol(0.5 g) r- isocyanic acid Butyl triethoxysilane, in 150 DEG C of N224 h are reacted under atmosphere.Product anhydrous benzene after reaction, anhydrous acetonitrile respectively wash one Time.It is dispersed in 25 ml anhydrous acetonitriles again, 350 mg glucose quantum dots, 0.3 mmol((6.6 mg is added) DABCO, in 90 DEG C of N224 h are reacted under atmosphere, are centrifuged, are finally placed in 80 DEG C of baking ovens with anhydrous acetonitrile, water, ethanol washing It is dry, obtain glucose quantum dot bonded silica gel chromatographic stationary phases.The glucose quantum dot bonded amount of the stationary phase is good, separation It works well, but relatively weaker compared with embodiment 2, but good compared with embodiment 3, separating effect is preferable.

Claims (9)

1. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material is by silica gel and r- isocyanatosilanes coupling agent It is uniformly mixed in benzene kind solvent, nitrogen or argon atmosphere protection are stirred to react 12 ~ 48h at 60 ~ 150 DEG C, and reaction product is used It is dispersed again in organic solvent after organic solvent washing, glucose quantum dot function monomer and catalyst triethylene is then added Diamines, N2Atmosphere, in 60 ~ 150 DEG C of 12 ~ 48 h of reaction；Use organic solvent and water washing after reaction, centrifugation, it is dry to get The silica gel chromatographic column filling material of glucose quantum dot modification.
2. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as described in claim 1, it is characterised in that: institute State the structure of r- isocyanatosilanes coupling agent are as follows: X3Si(CH2)mNCO, wherein X is methoxy or ethoxy, m=3 ~ 8.
3. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as claimed in claim 2, it is characterised in that: silicon The mass ratio of glue and r- isocyanatosilanes coupling agent is 1:1 ~ 4:1.
4. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as described in claim 1, it is characterised in that: silicon The mass ratio of glue and glucose quantum dot function monomer is 4:1 ~ 24:1.
5. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as described in claim 1, it is characterised in that: urge Be incorporated as glucose quantum dot function monomer quality 1 ~ 5% of agent triethylene diamine.
6. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as described in claim 1, it is characterised in that: benzene Class solvent is benzene,toluene,xylene.
7. a kind of preparation method of glucose quantum dot bonded silica gel chromatograph packing material as described in claim 1, it is characterised in that: have Solvent is DMF, acetonitrile, tetrahydrofuran.
8. the separation that the glucose quantum dot bonded silica gel chromatograph packing material of method preparation as described in claim 1 is used for carbohydrate.
9. point of the glucose quantum dot bonded silica gel chromatograph packing material of method preparation as described in claim 1 for base nucleosides From.
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