CN107857881A - A kind of covalent organic frame material and its synthetic method of benzoxazoles connection - Google Patents
A kind of covalent organic frame material and its synthetic method of benzoxazoles connection Download PDFInfo
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- CN107857881A CN107857881A CN201710986362.6A CN201710986362A CN107857881A CN 107857881 A CN107857881 A CN 107857881A CN 201710986362 A CN201710986362 A CN 201710986362A CN 107857881 A CN107857881 A CN 107857881A
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- fonnylphenyls
- frame material
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- ZGLHKEJAGHMUHR-UHFFFAOYSA-N O=Cc(cc1)ccc1-c1cc(-c2ccc(C=O)cc2)c(cc2)c3c1ccc(c(-c1ccc(C=O)cc1)c1)c3c2c1-c1ccc(C=O)cc1 Chemical compound O=Cc(cc1)ccc1-c1cc(-c2ccc(C=O)cc2)c(cc2)c3c1ccc(c(-c1ccc(C=O)cc1)c1)c3c2c1-c1ccc(C=O)cc1 ZGLHKEJAGHMUHR-UHFFFAOYSA-N 0.000 description 1
- GGSWCMIKSZKVJC-UHFFFAOYSA-N Oc(cc(c(O)c1)NCl)c1NCl Chemical compound Oc(cc(c(O)c1)NCl)c1NCl GGSWCMIKSZKVJC-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses the covalent organic frame material and its synthetic method of a kind of benzoxazoles connection.The synthetic method of the covalent organic frame material of the benzoxazoles connection of the present invention comprises the following steps：By 2; 4; 6 three (4 Fonnylphenyl) 1,3,5 triazine or 1; 3; 6,8 four (4 Fonnylphenyl) pyrenes and 2,5 dihydroxy 1; after 4 para-phenylene diamine dihydrochlorides are well mixed in organic solvent, are reacted under the catalysis of alkalescent catalyst and obtain covalent organic frame material.The covalent organic frame material of benzoxazoles connection produced by the present invention has the pore passage structure of larger specific surface area and rule, and stability is good.
Description
Technical field
The present invention relates to organic synthesis and field of functional materials, and in particular to a kind of benzoxazoles connection covalently has machine frame
Frame material and its synthetic method.
Background technology
Material changes the world, and during modern social development, material is indispensable composition.Have in all fields wide
General application, especially Porous materials, because of its good property, determine that it has very important application.In application process, material
Stability it is most important, directly affect the development prospect of material, can also govern its development.For such situation, open
The material of hair stability is of great importance.
Covalent organic frame material is a kind of emerging molecular sieve analog material, causes extensive concern, mesh in recent years
It is preceding in gas absorption/separation/storage, medicament slow release, photoelectricity (device), the preliminary application in field such as catalysis.It is covalently organic
The synthesis precursor of frame material is various, can regulate and control its structure and performance by changing precursor；It has big ratio table simultaneously
Area and orderly duct, are easy to the transmission of reaction raw materials and product；But covalent organic frame material stability governs it
Using.So the covalent organic frame material of synthesising stability is extremely important, the real of covalent organic frame material can be realized
Effect.
The content of the invention
To solve problems of the prior art, the present invention provides a kind of covalent organic frame material of benzoxazoles connection
Material and its synthetic method, the covalent organic frame material of benzoxazoles of the invention connection have larger specific surface area and rule
Pore passage structure then, and stability is good.
Specifically, the present invention provides a kind of synthetic method of the covalent organic frame material of benzoxazoles connection
It comprises the following steps：
By (4- the Fonnylphenyls) -1,3,5- triazines of 2,4,6- tri- or (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5-
After dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride is well mixed in organic solvent, reacted under the catalysis of alkalescent catalyst
To covalent organic frame material.
For example, by 2,4,6- tri- (4- Fonnylphenyls) -1,3,5-triazines and 2,5- dihydroxy-Isosorbide-5-Nitrae-p-phenylenediamine hydrochloric acid
After salt is well mixed in organic solvent, is reacted under the catalysis of alkalescent catalyst and obtain covalent organic frame material A.
By (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides in organic solvent
In be well mixed after, under the catalysis of alkalescent catalyst reaction obtain covalent organic frame material B.
Wherein, described 2,4,6- tri- (4- Fonnylphenyls) -1,3,5-triazines or 1,3,6,8- tetra- (4- Fonnylphenyls)
The mol ratio of pyrene and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides is 1:(1-2).In addition, the mol ratio is preferably 1:
1.5。
(4- the Fonnylphenyls) -1,3,5- triazines of 2,4,6- tri- are total with 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides
Concentration or the total concentration of (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides are
1-100g/L。
In addition, the organic solvent is the mixture or 1,3- dimethyl miaow of 1-METHYLPYRROLIDONE and mesitylene
The mixture of oxazoline ketone and mesitylene.
In addition, the alkalescent catalyst is one kind in benzimidazole, imidazoles, quinoline or isoquinolin.
In addition, the dosage of the alkalescent catalyst is 2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride mole dosages
0.8-40 times.
In addition, the reaction is carried out at 150-250 DEG C.
In addition, the synthetic method of the present invention, preferably described reaction occurs in the reactor of sealing, the reaction time five
My god, the covalent organic frame material that can obtain benzoxazoles connection is dried after centrifugation.
The present invention also provides a kind of covalent organic frame material of benzoxazoles connection made from synthetic method as described above
Material.
The covalent organic frame material of the benzoxazoles connection of the present invention has the structure of long-range order and the duct of rule.
The covalent organic frame material of the benzoxazoles connection of the present invention is to employ the new material that the mode of oxazole ring connection synthesizes,
Stability of the material in different solvent environments can be fully kept, makes material keep original property not change, especially
Soaked three days in strong acid and highly basic, the crystal formation of material and orderly duct can keep constant, and material will not occur point
Solution.
Brief description of the drawings
Fig. 1 is the X ray diffracting spectrum of product in embodiment 1.
Fig. 2 is LZU-191 solid state nmr spectrogram.
Fig. 3 is LZU-191 infrared spectrum.
Fig. 4 is LZU-191 nitrogen adsorption desorption curve and pore size distribution curve.
Fig. 5 is LZUI-191 thermogravimetric curve.
Fig. 6 is the X ray diffracting spectrum of the product of embodiment 2.
Fig. 7 is LZU-192 solid state nmr spectrogram.
Fig. 8 is LZU-192 infrared spectrum.
Fig. 9 is LZU-192 nitrogen adsorption desorption curve and pore size distribution curve.
Figure 10 is LZU-192 thermogravimetric curve.
Figure 11 is material LZU-191 respectively by boiling water, trifluoroacetic acid, 9M hydrochloric acid solutions and the processing of 9M sodium hydroxide solutions
X-ray diffractogram of powder spectrum afterwards.
Figure 12 is material LZU-192 respectively by boiling water, trifluoroacetic acid, 9M hydrochloric acid solutions and the processing of 9M sodium hydroxide solutions
X-ray diffractogram of powder spectrum afterwards.
Embodiment
The optimum condition of the present invention is described further with reference to embodiments, it will be appreciated that described herein
Preferred embodiment is merely to illustrate and explain the present invention, and is not intended to limit the present invention.
Unless otherwise instructed, by 2,4,6- tri- (4- Fonnylphenyls) -1,3,5-triazines and 2,5- dihydroxy-Isosorbide-5-Nitrae-to benzene
After diamine hydrochloride is well mixed in organic solvent, is reacted under the catalysis of alkalescent catalyst and obtain covalent organic frame material
Material A, which is ordered, is：LZU-191.
By (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides in organic solvent
In be well mixed after, under the catalysis of alkalescent catalyst reaction obtain covalent organic frame material B life be：LZU-192.
Embodiment 1：The covalent organic frame material LZU-191 of benzoxazoles connection synthesis
By (4- the Fonnylphenyls) -1,3,5- triazines of 26.1mg 2,4,6- tri- and 21.3mg 2,5- dihydroxy -1,4-
Para-phenylene diamine dihydrochloride is added to 10mL peaces and cutd open in bottle.Then 35.4mg benzimidazoles are added, 0.5mL N- first is added after shaking up
Base pyrrolidones and 0.5mL mesitylene.Peace is cutd open into bottle to be placed in liquid nitrogen, 0mbar is evacuated to after solution solidification, then will
Peace cuts open bottle sealing.It is placed in baking oven, is reacted five days in 180 DEG C.After reaction terminates, cuing open bottom of bottle portion in peace has solid generation,
Solid is transferred in centrifuge tube, with acetone, tetrahydrofuran difference centrifuge washing 3 times.Solid is dried at 100 DEG C, obtained
Brown solid powder LZU-191 28.5mg, yield 78%.
Fig. 1 is the X ray diffracting spectrum of product in embodiment 1, and wherein Fig. 1 a correspond to LZU-191, and Fig. 1 b correspond to 2,
4,6- tri- (4- Fonnylphenyls) -1,3,5-triazines, Fig. 1 c correspond to 2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride.Pass through
Contrast the x-ray diffractogram of powder spectrum of LZU-191 and raw material, it may be determined that the present invention has successfully synthesized a kind of new crystal formation material
Material.
Fig. 2 is LZU-191 solid state nmr spectrogram.
Fig. 3 is LZU-191 infrared spectrum, and wherein Fig. 3 a correspond to 2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride, is schemed
3b corresponds to 2,4,6- tri- (4- Fonnylphenyls) -1,3,5-triazines, and Fig. 3 c correspond to LZU-191.
Fig. 4 is LZU-191 nitrogen adsorption desorption curve and pore size distribution curve, and the as shown by data material has larger
Specific surface area and rule pore passage structure.
Fig. 5 is LZUI-191 thermogravimetric curve.
Embodiment 2：The stability covalent organic frame material LZU-192 of benzoxazoles connection synthesis
According to the method synthesis of embodiment 1 and sign.(4- Fonnylphenyls) pyrenes of 30.9mg 1,3,6,8- tetra- and 21.3mg
2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride, obtain yellow solid powder LZU-19233.4mg, yield 81%.
Fig. 6 is the X ray diffracting spectrum of the product of embodiment 2, and wherein Fig. 6 a correspond to LZU-192, and Fig. 6 b correspond to 1,3,
6,8- tetra- (4- Fonnylphenyls) pyrenes, Fig. 6 c correspond to 2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride.By contrasting LZU-
192 and raw material x-ray diffractogram of powder spectrum, it may be determined that the present invention successfully synthesized a kind of new crystal formation material.
Fig. 7 is LZU-192 solid state nmr spectrogram.
Fig. 8 is LZU-192 infrared spectrum, and wherein Fig. 8 a correspond to 2,5- dihydroxy-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride, is schemed
8b corresponds to 1,3,6,8- tetra- (4- Fonnylphenyls) pyrenes, and Fig. 8 c correspond to LZU-192.
Fig. 9 is LZU-192 nitrogen adsorption desorption curve and pore size distribution curve, and the as shown by data material has larger
Specific surface area and rule pore passage structure.
Figure 10 is LZU-192 thermogravimetric curve.
Test example：LZU-191 and LZU-192 stability test
Obtained LZU-191 and LZU-192 materials are respectively placed in boiling water, trifluoroacetic acid, 9M hydrochloric acid solutions and 9M hydrogen-oxygens
Change and soaked in sodium solution three days, then filter and retrieve material, test powders X-ray diffraction and nitrogen adsorption are real after drying
Test.
It can be kept by the crystal formation of the material after above-mentioned processing method, material does not decompose in processing procedure,
By pore-size distribution test it can be seen that the orderly duct of material is not destroyed, specific surface area can be kept well.
Figure 11 is material LZU-191 respectively by boiling water, trifluoroacetic acid, 9M hydrochloric acid solutions and the processing of 9M sodium hydroxide solutions
X-ray diffractogram of powder spectrum afterwards.
Figure 12 is material LZU-192 respectively by boiling water, trifluoroacetic acid, 9M hydrochloric acid solutions and the processing of 9M sodium hydroxide solutions
X-ray diffractogram of powder spectrum afterwards.
Finally it should be noted that：The preferred embodiments of the present invention are the foregoing is only, are not intended to limit the invention,
Although the present invention is described in detail with reference to the foregoing embodiments, for those skilled in the art, it still may be used
To be modified to the technical scheme described in foregoing embodiments, or equivalent substitution is carried out to which part technical characteristic.
Within the spirit and principles of the invention, any modification, equivalent substitution and improvements made etc., it should be included in the present invention's
Within protection domain.
Claims (8)
1. a kind of synthetic method of the covalent organic frame material of benzoxazoles connection, it is characterised in that comprise the following steps：
By (4- the Fonnylphenyls) -1,3,5- triazines of 2,4,6- tri- or (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5- dihydroxies
After base-Isosorbide-5-Nitrae-para-phenylene diamine dihydrochloride is well mixed in organic solvent, reacts and be total under the catalysis of alkalescent catalyst
Valency organic framework materials.
2. synthetic method according to claim 1, it is characterised in that described 2,4,6- tri- (4- Fonnylphenyls) -1,3,
5- triazines or the mol ratio of (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides are 1:
(1-2)。
3. synthetic method according to claim 1 or 2, it is characterised in that 2,4,6- tri- (4- Fonnylphenyls) -1,3,5-
The total concentration of triazine and 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides or (4- Fonnylphenyls) pyrenes of 1,3,6,8- tetra- with
The total concentration of 2,5- dihydroxy -1,4- para-phenylene diamine dihydrochlorides is 1-100g/L.
4. synthetic method according to claim 1, it is characterised in that the organic solvent is for 1-METHYLPYRROLIDONE and
The mixture or the mixture of 1,3- dimethyl-imidazolinones and mesitylene of trimethylbenzene.
5. synthetic method according to claim 1, it is characterised in that the alkalescent catalyst be benzimidazole, imidazoles,
One kind in quinoline or isoquinolin.
6. synthetic method according to claim 1, it is characterised in that the dosage of the alkalescent catalyst is 2,5- dihydroxies
0.8-40 times of base -1,4- para-phenylene diamine dihydrochloride mole dosages.
7. synthetic method according to claim 1, it is characterised in that the reaction is carried out at 150-250 DEG C.
What 8. benzoxazoles made from the synthetic method in a kind of 1-7 such as claim as described in any one connected covalently has machine frame
Frame material.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997589A (en) * | 2018-06-27 | 2018-12-14 | 兰州大学 | A kind of hydrophobic oleophilic oil covalent organic frame material and its synthetic method |
| CN110511391A (en) * | 2019-08-09 | 2019-11-29 | 武汉大学 | Covalent organic frame material and preparation method thereof with optical dynamic therapy effect |
| CN110672763A (en) * | 2019-09-10 | 2020-01-10 | 山东省分析测试中心 | Application of porous imine chain covalent organic framework material in estrogen detection |
| CN111138283A (en) * | 2020-01-07 | 2020-05-12 | 兰州大学 | Method for preparing chiral aldehyde compound by benzoxazole-linked covalent organic framework asymmetric photocatalysis |
| CN112625051A (en) * | 2020-12-18 | 2021-04-09 | 天津大学 | Donor-receptor covalent organic framework material, preparation method and photocatalytic application |
| CN113929876A (en) * | 2021-10-22 | 2022-01-14 | 西北师范大学 | Covalent organic framework material with C = C double-bond fluorescent probe and synthetic method and application thereof |
| CN114380965A (en) * | 2021-12-24 | 2022-04-22 | 江南大学 | Polybenzimidazole ionic covalent organic framework material BM-S and preparation method and application thereof |
| CN114570430A (en) * | 2020-11-30 | 2022-06-03 | 浙江工业大学 | Unit point gold-loaded covalent organic framework catalyst and preparation method and application thereof |
| CN115386083A (en) * | 2022-09-16 | 2022-11-25 | 河南农业大学 | 3, 4-ethylenedioxythiophene covalent triazine framework and synthesis method and application thereof |
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| CN108997589A (en) * | 2018-06-27 | 2018-12-14 | 兰州大学 | A kind of hydrophobic oleophilic oil covalent organic frame material and its synthetic method |
| CN110511391A (en) * | 2019-08-09 | 2019-11-29 | 武汉大学 | Covalent organic frame material and preparation method thereof with optical dynamic therapy effect |
| CN110672763A (en) * | 2019-09-10 | 2020-01-10 | 山东省分析测试中心 | Application of porous imine chain covalent organic framework material in estrogen detection |
| CN111138283B (en) * | 2020-01-07 | 2021-10-12 | 兰州大学 | Method for preparing chiral aldehyde compound by benzoxazole-linked covalent organic framework asymmetric photocatalysis |
| CN111138283A (en) * | 2020-01-07 | 2020-05-12 | 兰州大学 | Method for preparing chiral aldehyde compound by benzoxazole-linked covalent organic framework asymmetric photocatalysis |
| CN114570430A (en) * | 2020-11-30 | 2022-06-03 | 浙江工业大学 | Unit point gold-loaded covalent organic framework catalyst and preparation method and application thereof |
| CN114570430B (en) * | 2020-11-30 | 2023-12-05 | 浙江工业大学 | Single-site gold-loaded covalent organic framework catalyst and preparation method and application thereof |
| CN112625051B (en) * | 2020-12-18 | 2022-05-20 | 天津大学 | Donor-receptor covalent organic framework material, preparation method and photocatalytic application |
| CN112625051A (en) * | 2020-12-18 | 2021-04-09 | 天津大学 | Donor-receptor covalent organic framework material, preparation method and photocatalytic application |
| CN113929876A (en) * | 2021-10-22 | 2022-01-14 | 西北师范大学 | Covalent organic framework material with C = C double-bond fluorescent probe and synthetic method and application thereof |
| CN113929876B (en) * | 2021-10-22 | 2023-09-01 | 西北师范大学 | Fluorescent probe covalent organic framework material with C=C double bond, and synthesis method and application thereof |
| CN114380965A (en) * | 2021-12-24 | 2022-04-22 | 江南大学 | Polybenzimidazole ionic covalent organic framework material BM-S and preparation method and application thereof |
| CN114380965B (en) * | 2021-12-24 | 2023-02-07 | 江南大学 | Polybenzimidazole ionic covalent organic framework material BM-S and preparation method and application thereof |
| CN115386083A (en) * | 2022-09-16 | 2022-11-25 | 河南农业大学 | 3, 4-ethylenedioxythiophene covalent triazine framework and synthesis method and application thereof |
| CN115386083B (en) * | 2022-09-16 | 2024-02-27 | 河南农业大学 | 3, 4-ethylenedioxythiophene covalent triazine framework and synthetic method and application thereof |
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