CN108485652A - A kind of Porous-Organic particle and preparation method thereof - Google Patents
A kind of Porous-Organic particle and preparation method thereof Download PDFInfo
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Abstract
The present invention is using the dicarboxylic acids containing diacetylene base and the organic compound containing diamino as raw material, or using the diamine containing diacetylene base and containing there are two the dicarboxylic acids of carboxyl as raw material, Porous-Organic particle is prepared by self assembly, raw material sources are extensive, preparation method is simple, during the reaction, proton transfer occurs between carboxyl and amino, it is combined by the ionic bond of carboxyl and amino, prevent organic matter segment is from effectively accumulating, form organic porous granule, the Porous-Organic particle that the present invention obtains has very high specific surface area and Kong Rong, the identification function of polybutadiene alkynes polymer can be greatlyd improve.Moreover it is possible to be enough in the fields such as gas storage, separation, absorption, optics, the Porous-Organic particle that the present invention obtains has the diameter of 50 μm of 1nm.
Description
Technical field
The invention belongs to chemical fields, and in particular to a kind of Porous-Organic particle and preparation method thereof.
Background technology
Porous material is because solid with high specific surface area and Kong Rong, high chemical stability, low skeletal density etc.
There is property, is administering air pollution, gas separation, gas storage, photoelectric device, heterogeneous catalysis and chemical sensitisation and biology biography
The fields such as sense obtain extensive concern.Compared with traditional inorganic microporous material and metal-organic framework material, Porous-Organic particle
It is connected by covalent bond, ionic bond or intermolecular force, there is open duct and permanent porous.By organic molecule
The organic porous material of building block structure, there are many building modes, are broadly divided into：Chain closs packing is prevented by cross-linking reaction；It is logical
It crosses rigidity and distortion group prevents chain closs packing；Pass through conjugated pi-π system rigid structural components；Occurred by suitable functional group
It is prepared by reversibly condensation reaction.And the preparation method condition of Porous-Organic particle is harsh at present, monomer source is limited, limits
The development of Porous-Organic particle and extensive preparation.
Invention content
For the technical problem more than solving, the present invention provides that a kind of preparation method is simple, and raw material sources are widely organic
Porous granule and preparation method thereof, obtained Porous-Organic particle have stable porous structure and excellent fluorescence.
The object of the present invention is to provide a kind of with the dicarboxylic acids containing diacetylene base and contains the organic compound of diamino
Object be raw material or using the diamine containing diacetylene base and containing there are two the dicarboxylic acids of carboxyl as raw material be prepared it is organic more
Hole particle.
It is a further object of the present invention to provide a kind of easy to operate, above-mentioned porous granule is prepared using the method for self assembly
Method.
According to the Porous-Organic particle of the specific embodiment of the invention, by organic compound first and organic compound second from group
Dress synthesis,
The chemical formula of organic compound first is G-A-C ≡ C-C ≡ C-A-G,
Wherein：
A isIn one kind or more
Kind,
G is-COOH or-NH2,
N1, n2, n3 and n4 are the integer of separate 1-20；
The chemical formula of organic compound second is Q- (D)m-Z-(D)m- Q,
Wherein：
Z is the straight chained alkyl containing 2-20 carbon atom, to phenyl, naphthenic base, pyridyl group, pyrimidine radicals or naphthalene；
D is-CH2, to phenyl, naphthenic base, pyridyl group is one or more in pyrimidine radicals or naphthalene；M is the whole of 1-20
Number, wherein D are different from Z,
Q is-COOH or-NH2；
G is different from Q.
The compound of the present invention first contains two adjacent three keys, and what is be connected with two three keys can be methylene, amide
Base, ester group, the combination of one or more of ethyleneoxy, end group is carboxyl or amino, and the compound of the present invention second is with carboxylic
Base or amino are end group, and main chain includes containing multiple straight chained alkyls, to phenyl, naphthenic base, pyridyl group, pyrimidine radicals and naphthalene
In it is several, they combine to obtain with certain rule.Wherein organic compound first is different from the end group of organic compound second, it
End group in carrying out reaction process carboxyl and amino proton transfer occurs, form cavernous structure.
Preferably, the A is-CH2, n1 8, G are-COOH, i.e., organic compound first is 10,12-, 22 carbon diines
Diacid, it is further preferred that Z is to phenyl, D is-CH2, m 1, Q are-NH2, organic compound second is p dimethylamine.This
The Porous-Organic particle provided is invented by containing in main functional group carboxyl in organic compound first and organic compound second
Main functional group amino carry out self assembly and realizing proton transfer, form new functional group COO-And NH3+, due to organic compound
Proton transfer has occurred between object first and second so that organic matter segment cannot effectively be accumulated, to form cavernous structure.And 10,
Containing there are two three keys and two carboxyls in 22 carbon diine diacid of 12-, containing there are two amino in p dimethylamine, both have
Proton exchange has occurred after by self assembly in machine compound, passes through the combination of the ionic bond of carboxyl and amido, ethyl group and benzene
Ring respectively between Van der Waals force and the factors such as π-π active forces, form organic porous granule, by ultraviolet irradiation it
Afterwards, diacetylene base forms main chain by photopolymerization, forms polybutadiene alkynes polymer, and porous granule is after heating at this time, face
Color can become red from blue, and have the function of fluorescence.
According to the preparation method of the Porous-Organic particle of the specific embodiment of the invention, include the following steps：
(1) organic compound first and organic compound second are dissolved in same solvent respectively, then respectively at ultrasound
Reason, obtains first solution and second solution；
(2) the first solution and second solution that are obtained in step (1) are uniformly mixed, reaction, remove solvent, it is dry, obtain institute
State Porous-Organic particle.
Preferably, in step (1), the solvent is in tetrahydrofuran, chloroform, toluene, ethyl alcohol, isopropanol and n-hexane
It is a kind of.
Preferably, in step (1), the power of the supersound process is 10-15W, processing time 10-20min.In order to make
Organic compound first and second can be completely dissolved in organic solvent, and the present invention is before reactions, final to obtain using supersound process
To the uniform solution first solution and second solution fully dissolved, prepare for being smoothed out for subsequent reactions.
Preferably, further include standing 15-25min in step (1), after being ultrasonically treated, it is further preferred that the standing
Temperature be 20-30 DEG C.During supersound process, the temperature of first solution and second solution can increase, and the present invention provides
Self-assembling reaction can fully be reacted at 10-25 DEG C, in order to ensure being smoothed out for reaction process, by supersound process
Afterwards, first solution and second solution preferably reach room temperature by standing cooling treatment.
Preferably, in step (1), the molar ratio of the first solution and second solution is 5:1-25, it is further preferred that described
The molar concentration rate of first solution and second solution is 1:1, volume ratio 1:1.In the present invention, organic compound first is containing there are two carboxylics
Base, organic compound second contain there are two amino, their chemical equivalent is 1:1, but when first solution is excessive, first solution is that second is molten
Within 5 times of liquid, the organic compound first containing part, organic compound first are covered by porous granule in final product
In, polymerisation is occurred by ultraviolet irradiation, the excellent Porous-Organic particle of fluorescence can be obtained.When organic compound second
It is excessive, when second solution is within 5 times of first solution, there are the organic compound second of part, these organic compounds in final product
Object can be coated in porous granule, and the pore size of porous granule can be also adjusted during reaction.
Preferably, in step (2), the time of the reaction is 10-20min.
Beneficial effects of the present invention are：
The present invention is using the dicarboxylic acids containing diacetylene base and the organic compound containing diamino as raw material, or to contain
The diamine of diacetylene base and containing being raw material there are two the dicarboxylic acids of carboxyl, Porous-Organic particle is prepared by self assembly, former
Material derives from a wealth of sources, and preparation method is simple, during the reaction, proton transfer occurs between carboxyl and amino, passes through carboxyl and ammonia
The ionic bond of base combines so that organic matter segment cannot effectively be accumulated, and organic porous granule is formed, and the present invention obtains organic more
Hole particle has very high specific surface area and Kong Rong, can greatly improve the identification function of polybutadiene alkynes polymer.Moreover it is possible to
It is enough in the fields such as gas storage, separation, absorption, optics, the Porous-Organic particle that the present invention obtains is straight with 1nm-50 μm
Diameter.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
Obtain other attached drawings according to these attached drawings.
Fig. 1 is the infrared spectrogram for the Porous-Organic particle that the embodiment of the present invention 1 obtains；
Fig. 2 is the scanning electron microscope (SEM) photograph for the Porous-Organic particle that the embodiment of the present invention 1 obtains；
Fig. 3 is the transmission electron microscope picture for the Porous-Organic particle that the embodiment of the present invention 1 obtains；
Fig. 4 be the Porous-Organic particle that the embodiment of the present invention 1 obtains photopolymerization before after (a), photopolymerization (b) and
The optical microscope of (c) after heating；Before the photopolymerization of Porous-Organic particle after (d), photopolymerization (e) and heating after
(f) shows fluorescent microscopy images.
Specific implementation mode
To make the object, technical solutions and advantages of the present invention clearer, technical scheme of the present invention will be carried out below
Detailed description.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Base
Embodiment in the present invention, those of ordinary skill in the art are obtained all without making creative work
Other embodiment belongs to the range that the present invention is protected.
Embodiment 1
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
Object first is 10,12-, 22 carbon diine diacid (DCDDA), and structural formula is：
Organic compound second is p dimethylamine (pXDA), and structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take each self-dissolvings of pXDA of the DCDDA and 0.01362g of 0.03625g
Solution carries out 10 minutes supersound process in the tetrahydrofuran solvent of 10ml under 10W power, after supersound process, in room temperature item
It is kept for 20 minutes for (25 DEG C) under part.
Under normal temperature condition (25 DEG C), the DCDDA solution for taking 5ml is mixed with the pXDA solution of 5ml, reacts 10min, evaporation
Solvent, drying, obtains Porous-Organic particle.
Table 1 is the control table of the infrared spectrogram of Porous-Organic particle and raw material that embodiment 1 obtains.Fig. 1 is
The infrared spectrogram for the Porous-Organic particle that embodiment 1 obtains.DCDDA and pXDA warps are can be seen that from the result of Fig. 1 and table 1
It crosses after reaction, DCDDA is in 1698cm-1The C=O bond at place disappears, and carboxyl is consumed, and pXDA is in 3351cm-1The NH at place2It is not right
Claim stretching vibration peak and in 3279cm-1The symmetrical stretching vibration peak at place disappears, and the Porous-Organic particle formed is then in 1646cm-1There is NH in place3+Asymmetric bending vibration peak, in 1520cm-1There is the asymmetric stretching vibration peak of COO- in place,
1407cm-1There is COO in place-Symmetrical stretching vibration peak, this illustrates DCDDA and pXDA after reaction, the carboxyl of DCDDA and
Proton transfer has occurred between the amino of pXDA, generates new chemical bond NH3+And COO-.Fig. 2 is above-mentioned Porous-Organic particle
Scanning electron microscope (SEM) photograph, the different amplification factor from figure it can be seen that the present invention using DCDDA and pXDA be raw material pass through from
Group reaction cartridge, under with above-mentioned ratio and reaction condition, the diameter of obtained microsphere particles is about 5-15 μm, and what is obtained is micro-
Ball particle surface gathers porous structure.As can be seen that above-mentioned Porous-Organic particle surface is densely covered more from the transmission electron microscope picture of Fig. 3
Hole, inside have nuclear structure, have nucleocapsid.Above-mentioned Porous-Organic particle is can be seen that in ultraviolet irradiation from the result of Fig. 4
Later, by heating, particle has fluorescence.
The results of FT-IR of 1 embodiment 1 of table
Embodiment 2
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C20H36N2, structural formula is：
The chemical formula of organic compound second is to benzene dipropionic acid, and structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.005mol it is organic
Compound second is respectively dissolved in the toluene solvant of 10ml, and 20 minutes supersound process are carried out under 15W power, are ultrasonically treated it
Afterwards, it is kept for 15 minutes at 20 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 20min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 3
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C14H10O8, structural formula is：
The chemical formula of organic compound second is C16H24N2, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.005mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the chloroform solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, are ultrasonically treated it
Afterwards, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 4
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C12H14O6N8, structural formula is：
The chemical formula of organic compound second is C17H16O4, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the toluene solvant of 10ml, and 15 minutes supersound process are carried out under 10W power, are ultrasonically treated it
Afterwards, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 5
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C12H8O12N2, structural formula is：
The chemical formula of organic compound second is C17H28O4, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the alcohol solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, are ultrasonically treated it
Afterwards, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 6
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C14H10O8, structural formula is：
The chemical formula of organic compound second is C13H16N4, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the isopropanol solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, are ultrasonically treated it
Afterwards, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 7
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
Object first is 10,12-, 22 carbon diine diacid, and structural formula is：
The chemical formula of organic compound second is C11H14N6, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the n-hexane solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, are ultrasonically treated it
Afterwards, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 8
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
Object first is 10,12-, 22 carbon diine diacid, and structural formula is：
The chemical formula of organic compound second is C23H22N2, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the tetrahydrofuran solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, is ultrasonically treated
Later, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
Embodiment 9
A kind of Porous-Organic particle, by organic compound first and organic compound second self assembly, wherein organic compound
The chemical formula of object first is C18H32N2, structural formula is：
The chemical formula of organic compound second is C12H8O4N4, structural formula is：
The preparation method of above-mentioned Porous-Organic particle is：Take 0.001mol organic compound first and 0.001mol it is organic
Compound second is respectively dissolved in the tetrahydrofuran solvent of 10ml, and 15 minutes supersound process are carried out under 10W power, is ultrasonically treated
Later, it is kept for 25 minutes at 30 DEG C.
Under normal temperature condition (25 DEG C), the first solution for taking 5ml is mixed with the second solution of 5ml, reacts 15min, evaporates solvent,
Drying, obtains Porous-Organic particle.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, protection scope of the present invention should be based on the protection scope of the described claims.
Claims (10)
1. a kind of Porous-Organic particle, which is characterized in that by organic compound first and organic compound second self assembly,
The chemical formula of organic compound first is G-A-C ≡ C-C ≡ C-A-G,
Wherein：
A isIn it is one or more,
G is-COOH or-NH2,
N1, n2, n3 and n4 are the integer of separate 1-20；
The chemical formula of organic compound second is Q- (D)m-Z-(D)m- Q,
Wherein：
Z is the straight chained alkyl containing 2-20 carbon atom, to phenyl, naphthenic base, pyridyl group, pyrimidine radicals or naphthalene；
D is-CH2, to phenyl, naphthenic base, pyridyl group is one or more in pyrimidine radicals or naphthalene；M is the integer of 1-20,
Middle D is different from Z,
Q is-COOH or-NH2；
G is different from Q.
2. Porous-Organic particle according to claim 1, which is characterized in that A is-CH2, n1 8, G are-COOH, organic
Compound first is 22 carbon diine diacid of 10,12-.
3. Porous-Organic particle according to claim 2, which is characterized in that Z is to phenyl, and D is-CH2, m 1, Q be-
NH2, organic compound second is p dimethylamine.
4. the preparation method of any Porous-Organic particles of claim 1-3, which is characterized in that include the following steps：
(1) organic compound first and organic compound second are dissolved in same solvent respectively, are then ultrasonically treated respectively, obtained
To first solution and second solution；
(2) the first solution and second solution that are obtained in step (1) are uniformly mixed, reaction, remove solvent, it is dry, it obtains described having
Machine porous granule.
5. the preparation method of Porous-Organic particle according to claim 4, which is characterized in that in step (1), the solvent
For one kind in tetrahydrofuran, chloroform, toluene, ethyl alcohol, isopropanol and n-hexane.
6. the preparation method of Porous-Organic particle according to claim 4, which is characterized in that in step (1), the ultrasound
The power of processing is 10-15W, processing time 10-20min.
7. the preparation method of Porous-Organic particle according to claim 4, which is characterized in that in step (1), be ultrasonically treated
Further include standing 15-25min later.
8. the preparation method of Porous-Organic particle according to claim 7, which is characterized in that in step (1), the standing
Temperature be 20-30 DEG C.
9. the preparation method of Porous-Organic particle according to claim 4, which is characterized in that in step (1), the first is molten
The molar ratio of liquid and second solution is 5:1-25.
10. the preparation method of Porous-Organic particle according to claim 4, which is characterized in that described anti-in step (2)
The time answered is 10-20min.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112679744A (en) * | 2020-12-04 | 2021-04-20 | 北京理工大学 | Method for converting two-dimensional COFs material into three-dimensional COFs material |
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|---|---|---|---|---|
| CN112679744A (en) * | 2020-12-04 | 2021-04-20 | 北京理工大学 | Method for converting two-dimensional COFs material into three-dimensional COFs material |
| CN112679744B (en) * | 2020-12-04 | 2022-11-18 | 北京理工大学 | Method for converting two-dimensional COFs material into three-dimensional COFs material |
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