CN109535393A - The preparation method and products thereof of micropore organic polymer nanosphere - Google Patents
The preparation method and products thereof of micropore organic polymer nanosphere Download PDFInfo
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
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- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
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- C08G2261/40—Polymerisation processes
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- C08G2261/411—Suzuki reactions
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Abstract
The present invention relates to a kind of methods and product that micropore organic polymer nanosphere is synthetically prepared using silica solution as auxiliary additive.It is put forward for the first time in the synthesis for applying to microporous polymer nano material using silica solution as nanotopography controlling agent, disclose a kind of using the silica solution that partial size is 10-20 nm or so as auxiliary, the method that the microporous polymer nanosphere that partial size is 500 nm or so is synthetically prepared by transition metal-catalyzed metal coupling reaction in the solution.Silica solution is a kind of spherical silicones particle that partial size is 10-20 nm, silica solution plays the role of a kind of spherical nuclei during microporous polymer molecular growth, microporous polymer strand can be using silica sol granule as core during aggregation growth, and being adsorbed on organic silicon granule surface, gradually aggregation growth becomes microporous polymer nanosphere.The method is simple to operation, stability is good, yield is high, and the polymer nano-microspheres pattern synthesized is uniform.
Description
Technical field
The present invention relates to a kind of preparation methods and products thereof of micropore organic polymer nanosphere.More particularly to a kind of benefit
Silica solution is used to be synthetically prepared the method and product of micropore organic polymer nanosphere as auxiliary additive.
Background technique
Micropore organic polymer material belongs to one kind of porous organic polymer material, mainly utilize two kinds containing multiple
The rigid organic monomer molecule of reaction site is synthetically prepared in the solution, and when synthesis, used polymerization reaction was mainly
Sonogashira coupling reaction, Oxidative coupling reaction and Yamamoto coupling reaction etc..Since it is by two kinds of rigidity
Organic monomer molecule, which is cross-linked with each other, to be polymerized, and at three dimensional network structure between strand, therefore its material itself contains
Microcellular structure.In addition to this, since the polymerization process of two kinds of rigid molecules is mixed and disorderly unordered multiple reaction site while diverging is poly-
Close, therefore, finally synthesize obtained material microscopic appearance be in a jumble it is unordered, mainly by nanosphere, nanometer sheet, nano wire with
And irregular nano particle composition.
Since the microcosmic nanotopography of micropore organic polymer material is disorderly and unsystematic, it is hindered in catalysis, the energy, environment
And the application in the fields such as photoelectric sensor, people do a lot of work in terms of the control synthesis of its nanotopography in recent years, than
Synthetic microporous polymer nanocomposite film, the synthetic microporous polymer nano rice noodles of regulation monomer molecule structure are such as controlled by template and are received
Rice ball etc..But since above method operates extremely complex, it is difficult widely to be promoted, for example close by regulatory molecule structure
It is related to complicated Molecular Design and organic synthesis process at the method for microporous polymer nano wire or nanosphere, it is not only time-consuming
Length, yield is very low and nanotopography controllability is bad, therefore greatly limits its popularization and application.Currently, a kind of letter not yet
It is single effectively, the good method of stability realize the synthesis of micropore organic polymer nanosphere.
Summary of the invention
In view of the deficiencies of the prior art, it is an object of that present invention to provide the preparation sides of micropore organic polymer nanosphere
Method.
Another object of the present invention is: the micropore organic polymer nanosphere for providing a kind of above method preparation produces
Product.
The object of the invention is realized by following proposal: a kind of preparation method of micropore organic polymer nanosphere utilizes
For silica sol granule as auxiliary, being synthetically prepared partial size in the solution by transition metal-catalyzed metal coupling reaction is 500 nm
The microporous polymer nanosphere of left and right, includes the following steps:
A, it weighs silica solution to be added in organic solvent, be diluted by 1g silica solution and 10ml organic solvent proportion, and ultrasonic disperse
5-10 min obtains silica solution dispersion liquid；
B, according to the requirement of transition metal-catalyzed metal coupling reaction, select two kinds of rigid organic molecule monomers former as polymerization
Material weighs the above monomer according to reaction ratio and is added in the silica solution dispersion liquid, after stirring 10 min, is added thereto
Catalyst needed for reaction, wherein transition metal-catalyzed metal coupling reaction type include: Sonogashira coupling reaction,
Oxidative coupling reaction, Yamamoto coupling reaction or Suzuki coupling reaction；
C, after catalyst is added, by vacuumize-operation of inflated with nitrogen comes out the air displacement in reaction solution；
D, then under nitrogen protection, it is to slowly warm up to 60-90 DEG C of set temperature, and quickly stir；
E, solid powder is filtered and collected after reacting 6h, after successively being rinsed with acetone, tetrahydrofuran, ethyl alcohol, uses vacuum oven
Dry 12h, obtains powdered product；
F, obtained powder made above is added in 3% hydrofluoric acid solution and is stirred to react 6h, it is therefore an objective to micropore will be remained in
The silica sol granule on polymer nano-microspheres surface etches removal, obtains required product.
The partial size of the silica sol granule is 10-20 nm, and the organic solvent of silica solution is in benzene,toluene,xylene
One kind or any combination thereof object.
The present invention provides a kind of micropore organic polymer nanosphere, partial size, which is prepared, according to any of the above-described method is
The microporous polymer nanosphere of 500 nm or so.
Silica solution that partial size is 10-20 nm or so is utilized as nanotopography controlling agent in the present invention for the first time, passes through transition
The metal coupling reaction of metal catalytic has been synthetically prepared the microporous polymer nanosphere that partial size is 500 nm or so in the solution.
Mechanism of the present invention is: silica solution is a kind of spherical silicones particle that partial size is 10-20 nm, and silica solution is in micropore
Polymer molecule plays the role of a kind of spherical nuclei during growing, and microporous polymer strand is during aggregation growth
Can be using silica sol granule as core, being adsorbed on organic silicon granule surface, gradually aggregation growth becomes microporous polymer nanosphere.
The present invention is advantageous in that: the method is simple to operation, stability is good, yield is high, and the polymer nano synthesized
Meter Wei Qiu pattern is uniform.
Detailed description of the invention
Fig. 1 is the SEM figure for the microporous polymer nanosphere that the embodiment of the present invention 1 synthesizes；
Fig. 2 is the SEM figure for the microporous polymer nanosphere that the embodiment of the present invention 3 synthesizes.
Specific embodiment
The present invention is described in detail below by specific example, but protection scope of the present invention is not only restricted to these
Examples of implementation.
Embodiment 1
A kind of preparation method of micropore organic polymer nanosphere, by transition metal-catalyzed metal coupling reaction in solution
In be synthetically prepared the microporous polymer nanosphere that partial size is 500 nm or so, comprising the following steps:
A, weighing 2.0g partial size is about that 20 nm or so are dispersed in the xylene solvent that silica solution in toluene solvant is added to 20 ml
Middle 10 min of ultrasonic disperse；
B, according to the requirement of Sonogashira coupling reaction, the 1 of 52 mg is weighed, the 4 of 3,5- tri- acetylene benzene monomers and 135mg,
4 '-diiodide monomers, are added in the dispersion liquid of above-mentioned silica solution, and after stirring 5 min, the triphen of catalytic amount is added thereto
Base phosphine dichloride palladium and cuprous iodide catalyst and 10 ml triethylamines；
C, after catalyst is added, by vacuumize-operation of inflated with nitrogen comes out the air displacement in reaction solution；
D, then under nitrogen protection, above-mentioned reaction solution is to slowly warm up to 60 DEG C and is quickly stirred, and is quickly stirred；
E, reaction solution is filtered after reacting 6h and collects solid, after successively being rinsed with acetone, tetrahydrofuran, ethyl alcohol, with vacuum drying
The powder that the dry 12h of case is obtained；
F, obtained powder made above is added in 3% hydrofluoric acid solution and is stirred to react 6h, it is therefore an objective to micropore will be remained in
The silica sol granule on polymer nano-microspheres surface etches removal.The SEM figure for synthesizing obtained microporous polymer nanosphere is shown in
Fig. 1 has the characteristics that pattern is uniform.
Embodiment 2
A kind of preparation method of micropore organic polymer nanosphere, includes the following steps:
A, weighing 2.0g partial size is about that 10 nm or so are dispersed in the xylene solvent that silica solution in toluene solvant is added to 20 ml
Middle 10 min of ultrasonic disperse；
B, according to the requirement of Sonogashira coupling reaction, weigh 109 mg Isosorbide-5-Nitrae-diiodo- benzene monomer and 52 mg 1,3,5-
Three acetylene benzene monomers, are added in the dispersion liquid of above-mentioned silica solution, and after stirring 5 min, the triphenyl of catalytic amount is added thereto
Phosphine dichloride palladium and cuprous iodide catalyst and 10 ml triethylamines；
C, after catalyst is added, by vacuumize-operation of inflated with nitrogen comes out the air displacement in reaction solution；
D, then under nitrogen protection, above-mentioned reaction solution is to slowly warm up to 60 DEG C, and quickly stir；
E, reaction solution is filtered after reacting 6h and collects solid, after successively being rinsed with acetone, tetrahydrofuran, ethyl alcohol, with vacuum drying
Case dries 12h；
F, obtained powder made above is added in 3% hydrofluoric acid solution and is stirred to react 6h, it is therefore an objective to micropore will be remained in
The silica sol granule on polymer nano-microspheres surface etches removal.
Embodiment 3
A kind of preparation method of micropore organic polymer nanosphere, includes the following steps:
A, weighing 2.0g partial size is about that 20 nm or so are dispersed in silica solution in toluene solvant and are added in the toluene solvant of 40 ml
10 min of ultrasonic disperse；
B, according to the requirement of Suzuki coupling reaction, weigh the 1 of 91 mg, 3,5- triiodo benzene monomers and 50 mg to benzene hypoboric acid
Monomer is added in the dispersion liquid of above-mentioned silica solution, 10 min of ultrasonic disperse, after the triphenylphosphine two of catalytic amount is added thereto
The wet chemical that palladium chloride catalyst and 1 ml concentration are 10 mg/ml, and 5 min of ultrasonic dissolution；
C, after catalyst is added, by vacuumize-operation of inflated with nitrogen comes out the air displacement in reaction solution；
D, then under nitrogen protection, above-mentioned reaction solution is to slowly warm up to 90 DEG C and is quickly stirred；
E, reaction solution is filtered after reacting 6h and collects solid, after successively being rinsed with acetone, tetrahydrofuran, ethyl alcohol, with vacuum drying
Case dries 12h；
F, obtained powder made above is added in 3% hydrofluoric acid solution and is stirred to react 6h, it is therefore an objective to micropore will be remained in
The silica sol granule on polymer nano-microspheres surface etches removal.The SEM of the microporous polymer nanosphere of synthesis schemes such as Fig. 2 institute
Show there is that pattern is uniform.
Claims (5)
1. a kind of preparation method of micropore organic polymer nanosphere, it is characterised in that using silica sol granule as auxiliary,
The microporous polymer that partial size is 500 nm or so is synthetically prepared in the solution by transition metal-catalyzed metal coupling reaction to receive
Meter Wei Qiu includes the following steps:
A, it weighs silica solution to be added in the organic solvent of certain volume, be diluted by 1g silica solution and 10ml organic solvent proportion,
And ultrasonic disperse 5-10 min, obtain silica solution dispersion liquid；
B, according to the requirement of transition metal-catalyzed metal coupling reaction, select two kinds of rigid organic molecule monomers former as polymerization
Material, weighs the above monomer according to reaction ratio and is added in silica solution dispersion liquid, and after stirring 10 min, reaction institute is added thereto
The catalyst needed, wherein transition metal-catalyzed metal coupling reaction type include: Sonogashira coupling reaction,
Oxidative coupling reaction, Yamamoto coupling reaction or Suzuki coupling reaction；
C, after catalyst is added, by vacuumize-operation of inflated with nitrogen comes out the air displacement in reaction solution；
D, then under nitrogen protection, it is to slowly warm up to 60-90 DEG C of set temperature, and quickly stir；
E, solid powder is filtered and collected after reacting 6h, after successively being rinsed with acetone, tetrahydrofuran, ethyl alcohol, uses vacuum oven
Dry 12h；
F, obtained powder made above is added in 3% hydrofluoric acid solution and is stirred to react 6h, it is therefore an objective to micropore will be remained in
The silica sol granule on polymer nano-microspheres surface etches removal, obtains required product.
2. the preparation method of micropore organic polymer nanosphere according to claim 1, it is characterised in that the silicon is molten
The partial size of glue particle is 10-20 nm, and the organic solvent of silica solution is one of benzene,toluene,xylene or any combination thereof
Object.
3. the preparation method of micropore organic polymer nanosphere according to claim 1, it is characterised in that the transition
The metal coupling reaction type of metal catalytic weighs 52 according to the requirement of the coupling reaction for Sonogashira coupling reaction
4, the 4 '-diiodide monomers of the 1 of mg, 3,5- tri- acetylene benzene monomers and 109-135mg are added to point of above-mentioned 20ml silica solution
In dispersion liquid, after stirring 5 min, the triphenylphosphine palladium and cuprous iodide catalyst and 10 of catalytic amount are added thereto
Ml triethylamine.
4. the preparation method of micropore organic polymer nanosphere according to claim 1, it is characterised in that the transition
The metal coupling reaction type of metal catalytic is the requirement of Suzuki coupling reaction, weighs the 1 of 91 mg, 3,5- triiodo benzene monomers
With 50 mg to benzene bis boronic acid monomer, it is added in the dispersion liquid of above-mentioned 40 ml silica solution, after 10 min of ultrasonic disperse, to
The wet chemical that the triphenylphosphine palladium catalyst and 1 ml concentration that catalytic amount is wherein added are 10 mg/ml.
5. a kind of micropore organic polymer nanosphere, it is characterised in that -4 any the methods are prepared into according to claim 1
The microporous polymer nanosphere for being 500 nm or so to partial size.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110180474A (en) * | 2019-06-02 | 2019-08-30 | 上海纳米技术及应用国家工程研究中心有限公司 | The preparation method and product of the micropore organic polymer nano-hollow microballoon of titanium dioxide nanometer microballoons auxiliary |
| CN110183715A (en) * | 2019-05-31 | 2019-08-30 | 上海纳米技术及应用国家工程研究中心有限公司 | The preparation method and products thereof of the micropore organic polymer of class moonscape pit pattern |
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| CN104785301A (en) * | 2015-03-13 | 2015-07-22 | 苏州至善化学有限公司 | Magnetic palladium composite catalyst, and preparation method and use thereof |
| CN104795247A (en) * | 2015-04-28 | 2015-07-22 | 中科院广州化学有限公司南雄材料生产基地 | Polyaniline nano-composite electrode material with porous structure, preparation method of polyaniline nano-composite electrode material and application of polyaniline nano-composite electrode material |
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| CN104785301A (en) * | 2015-03-13 | 2015-07-22 | 苏州至善化学有限公司 | Magnetic palladium composite catalyst, and preparation method and use thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110183715A (en) * | 2019-05-31 | 2019-08-30 | 上海纳米技术及应用国家工程研究中心有限公司 | The preparation method and products thereof of the micropore organic polymer of class moonscape pit pattern |
| CN110183715B (en) * | 2019-05-31 | 2022-07-01 | 上海纳米技术及应用国家工程研究中心有限公司 | Preparation method of microporous organic polymer with moon-like surface pit morphology and product thereof |
| CN110180474A (en) * | 2019-06-02 | 2019-08-30 | 上海纳米技术及应用国家工程研究中心有限公司 | The preparation method and product of the micropore organic polymer nano-hollow microballoon of titanium dioxide nanometer microballoons auxiliary |
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