CN110041264A - A kind of adamantyl glyoxaline ion liquid and preparation method thereof - Google Patents
A kind of adamantyl glyoxaline ion liquid and preparation method thereof Download PDFInfo
- Publication number
- CN110041264A CN110041264A CN201910287735.XA CN201910287735A CN110041264A CN 110041264 A CN110041264 A CN 110041264A CN 201910287735 A CN201910287735 A CN 201910287735A CN 110041264 A CN110041264 A CN 110041264A
- Authority
- CN
- China
- Prior art keywords
- preparation
- adamantyl
- reaction
- crude product
- bromo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of adamantyl glyoxaline ion liquid and preparation method thereof, the chemical formulas of the adamantyl glyoxaline ion liquid are as follows:In formula, n=9 or 11；R is-CH2CH3Or-CH3.The preparation process of adamantyl glyoxaline ion liquid of the present invention mainly includes two step of synthesis and quaternization reaction of 1- adamantanecarboxylic acid bromo Arrcostab.Reaction condition is mild, and raw material is easy to get, and product purity is high.For ionic liquid of the present invention due to containing adamantane group, the guest molecule that can be used as beta-cyclodextrin is used to surpass the self assembly of amphiphile, amphiphilic molecule, can also have important application in fields such as detergent, medicinal slow release agent, function nano materials.
Description
Technical field
The invention belongs to ionic liquid preparation method technical fields, are related to adamantane, especially a kind of adamantyl imidazoles
Class ionic liquid and preparation method thereof.
Background technique
Adamantane (tricyclic [3.3.1.13,7] decane) it is a kind of ring-type four being made of 10 carbon atoms and 16 hydrogen atoms
Face body hydrocarbon, entire ring system have straight symmetrical, highly stable structure feature.This rigidity ring system and straight symmetrical
Structure determines that adamantane and its derivative have unique physicochemical properties: non-toxic and tasteless, density is big, fusing point is high, hot steady
It is qualitative it is good, fat-soluble it is good, bioactivity is high, antiviral property is strong, extreme oleophylic etc..
In supramolecular chemistry, beta-cyclodextrin and adamantane are a pair of classical Host-guest Recognition molecules, between the two can
Highly stable inclusion complex is enough formed, binding constant between the two can reach 105M-1.1 bridge-head tertiary carbon position of adamantane is drawn
Enter long chain quaternary, both improved the amphipathic of molecule, also will not influence in conjunction with the Subjective and Objective of cyclodextrin, utilizes β-CD and gold
The intermolecular strong noncovalent interaction of rigid alkane, being widely used as intermolecular connection bridge, modified, drug carries for surface
The fields such as body, nano material.
By retrieval, it is not yet found that related patents are reported.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of adamantyl glyoxaline ion liquid, reaction condition temperature
With raw material is easy to get, and operation is simple.
Realize that the technical solution of the object of the invention is as follows:
A kind of adamantyl glyoxaline ion liquid, chemical formula are as follows:
In formula, n=9 or 11；R is-CH2CH3Or-CH3
A kind of synthetic method of adamantyl glyoxaline ion liquid, comprising the following steps:
(1) it is esterified: 1- adamantanecarboxylic acid, bromhydrin, catalyst and organic solvent is added to equipped with water segregator, condenser
In the reaction vessel of agitating device, be warming up to 80 DEG C~120 DEG C reaction 12h~for 24 hours, remove after reaction solid impurity and
Solvent obtains crude product, and for crude product after ethyl acetate dissolves after saturated sodium carbonate, distillation washing, drying crosses silicagel column after purification
Obtain 1- adamantanecarboxylic acid bromo Arrcostab.
(2) quaternary ammoniated: 1- adamantanecarboxylic acid bromo Arrcostab and N- alkyl imidazole that the step 1 obtains are added to
In reaction vessel equipped with condenser and agitating device, and be added organic solvent be uniformly mixed, in 50 DEG C~80 DEG C reaction for 24 hours~
48h removes solvent after reaction and obtains crude product, and crude product is dried to obtain adamantyl imidazole-like ionic liquid after recrystallization 2 times
Body.
Moreover, bromhydrin described in step (1) is the mixed of the one or two of the bromo- 1 nonyl alcohol of 9-, the bromo- 1- undecyl alcohol of 11-
Close object.
Moreover, the molar ratio of step (1) 1- adamantanecarboxylic acid and bromhydrin are as follows: 1:1~2.
Moreover, catalyst described in step (1) is one of butyl titanate, sulfamic acid, p-methyl benzenesulfonic acid or two
Kind or more mixture.
Moreover, the molar ratio of catalyst described in step (1) and 1- adamantanecarboxylic acid is 1:20~50.
Moreover, organic solvent described in step (1) is one of toluene, n,N-Dimethylformamide, n-hexane or two
Kind or more mixture.
Moreover, N- alkyl imidazole described in step (2) is N- methylimidazole or N- ethyl imidazol(e).
Moreover, the molar ratio of step (2) N- alkyl imidazole and 1- adamantanecarboxylic acid bromo Arrcostab is 1:0.5~1.
Moreover, step (2) organic solvent is acetonitrile or acetone.
The invention has the following beneficial effects:
(1) it is raw material that the present invention provides one kind by adamantanecarboxylic acid, has synthesized Buddha's warrior attendant through esterification, quaternary ammoniated two-step reaction
Alkyl imidazole ionic liquid.It is mild with reaction condition, the advantages that raw material is easy to get, and operation is simple, catalysis, battery,
The fields such as nano material have potential application prospect.
(2) the resulting ionic liquid of the present invention introduces long chain quaternary in adamantane bridge-head tertiary carbon position (No. 1 position), both improves
Molecule it is amphipathic, and will not influence in conjunction with the Subjective and Objective of beta-cyclodextrin.Have in supramolecular chemistry field and potentially answers
Use prospect.
(3) the resulting ionic liquid of the present invention has reaction condition mild, and raw material is easy to get, and operation is simple, in oversubscription
The fields such as sub- chemistry, surfactant, medicinal slow release agent, function nano material have potential application prospect.
Detailed description of the invention
Fig. 1 be a kind of hydrogen nuclear magnetic resonance of adamantyl glyoxaline ion liquid prepared by the present invention (1H-NMR) spectrogram,
Solvent for use is D2O。
Fig. 2 is a kind of infared spectrum of adamantyl glyoxaline ion liquid prepared by the present invention.
Fig. 3 is a kind of surface tension of adamantyl glyoxaline ion liquid prepared by the present invention with concentration curve
Figure.
Fig. 4 is a kind of conductivity of adamantyl glyoxaline ion liquid prepared by the present invention with concentration curve figure.
Fig. 5 is a kind of adamantyl glyoxaline ion liquid and beta-cyclodextrin prepared by the present invention according to 1:1 ratio1H-1H 2D ROESY NMR two dimension hydrogen spectrogram, solvent for use D2O。
Fig. 6 is a kind of grain size distribution of adamantyl glyoxaline ion liquid prepared by the present invention.
Fig. 7 is that a kind of adamantyl glyoxaline ion liquid and beta-cyclodextrin prepared by the present invention are formed according to 1:1 ratio
The transmission electron microscope picture of aqueous solution.
Specific embodiment
The invention will be further described with reference to the accompanying drawing and by specific embodiment, and following embodiment is descriptive
, it is not restrictive, this does not limit the scope of protection of the present invention.
Embodiment 1:
Adamantyl glyoxaline ion liquid (n=9；R is-CH3) preparation
(1) by the bromo- 1 nonyl alcohol 2.23g (10mmol) of 1- adamantanecarboxylic acid 1.80g (10mmol), 9-, p-methyl benzenesulfonic acid
0.034g (0.2mmol) and toluene are added in the reaction vessel equipped with water segregator, condenser and agitating device, are warming up to 100
DEG C reaction 12h, removes solid impurity and solvent after reaction and obtains crude product, crude product is after ethyl acetate dissolves through unsaturated carbonate
It is dry after sodium, distillation washing, it crosses silicagel column and obtains 1- adamantanecarboxylic acid -9- bromine nonyl ester, yield 76% after purification.
(2) the 1- adamantanecarboxylic acid -9- bromine nonyl ester 1.54g (4mmol) and N- methylimidazole obtained the step (1)
0.33g (4mmol) is added in the reaction vessel equipped with condenser and agitating device, and acetonitrile is added and is uniformly mixed, in 80 DEG C
React 48h, remove solvent after reaction and obtain crude product, crude product after recrystallization 2 times, be dried to obtain adamantyl imidazoles from
Sub- liquid, yield 87%.
Embodiment 2:
Adamantyl glyoxaline ion liquid (n=9；R is-CH2CH3) preparation
(1) by the bromo- 1 nonyl alcohol 4.46g (20mmol) of 1- adamantanecarboxylic acid 1.80g (10mmol), 9-, sulfamic acid 0.03g
(0.3mmol) and n-hexane are added in the reaction vessel equipped with water segregator, condenser and agitating device, are warming up to 80 DEG C of reactions
16h, removes solid impurity after reaction and solvent obtains crude product, and crude product is after ethyl acetate dissolves through saturated sodium carbonate, steaming
It is dry after distilled water is washed, it crosses silicagel column and obtains 1- adamantanecarboxylic acid -9- bromine nonyl ester, yield 80% after purification.
(2) the 1- adamantanecarboxylic acid -9- bromine nonyl ester 1.54g (4mmol) and N- ethyl imidazol(e) obtained the step (1)
0.19g (2mmol) is added in the reaction vessel equipped with condenser and agitating device, and acetone is added and is uniformly mixed, in 60 DEG C
React 36h, remove solvent after reaction and obtain crude product, crude product after recrystallization 2 times, be dried to obtain adamantyl imidazoles from
Sub- liquid, yield 82%.
Embodiment 3:
Adamantyl glyoxaline ion liquid (n=11；R is-CH3) preparation
(1) by the bromo- 1- undecyl alcohol 3.77g (15mmol) of 1- adamantanecarboxylic acid 1.80g (10mmol), 11-, butyl titanate
0.17g (0.5mmol) and n-hexane are added in the reaction vessel equipped with water segregator, condenser and agitating device, are warming up to 80
DEG C reaction for 24 hours, removes solid impurity and solvent after reaction and obtains crude product, crude product is after ethyl acetate dissolves through unsaturated carbonate
It is dry after sodium, distillation washing, it crosses silicagel column and obtains 11 ester of 1- adamantanecarboxylic acid -11- bromine, yield 79% after purification.
(2) the 11 ester 1.64g (4mmol) of 1- adamantanecarboxylic acid -11- bromine and N- methyl obtained the step (1)
Imidazoles 0.33g (4mmol) is added in the reaction vessel equipped with condenser and agitating device, and acetone is added and is uniformly mixed, in
50 DEG C of reaction 48h remove solvent after reaction and obtain crude product, and crude product is dried to obtain adamantyl imidazoles after recrystallization 2 times
Class ionic liquid, yield 75%.
Embodiment 4:
Adamantyl glyoxaline ion liquid (n=9；R is-CH3) preparation
(1) by the bromo- 1- undecyl alcohol 5.02g (20mmol) of 1- adamantanecarboxylic acid 1.80g (10mmol), 11-, sulfamic acid
0.03g (0.3mmol) and N,N-dimethylformamide are added to the reaction vessel equipped with water segregator, condenser and agitating device
In, 120 DEG C of reaction 12h are warming up to, solid impurity is removed after reaction and solvent obtains crude product, crude product is dissolved through ethyl acetate
It is dry after saturated sodium carbonate, distillation washing, it crosses silicagel column and obtains 11 ester of 1- adamantanecarboxylic acid -11- bromine after purification, produce
Rate 78%.
(2) the 11 ester 1.64g (4mmol) of 1- adamantanecarboxylic acid -11- bromine and N- ethyl obtained the step (1)
Imidazoles 0.29g (3mmol) is added in the reaction vessel equipped with condenser and agitating device, and acetonitrile is added and is uniformly mixed, in
80 DEG C of reactions for 24 hours, remove solvent after reaction and obtain crude product, crude product is dried to obtain adamantyl imidazoles after recrystallization 2 times
Class ionic liquid, yield 81%.
Application examples 1:
Surface-active test
Surface tension is measured in EZ-Piplus surface tension instrument, its surface tension is with concentration result of variations at 25 DEG C
As shown in Figure 3.Test result shows: using the critical micelle concentration CMC of the ionic liquid sample of the acquisition of embodiment 3 for 2 × 10- 3Mol/L, surface tension 46.8mN/m.
Electrical conductivity method test measured on DDS-307 conductivity meter, at 25 DEG C its conductivity with concentration result of variations such as
Shown in Fig. 4.Test result shows: using the critical micelle concentration CMC of the ionic liquid sample of the acquisition of embodiment 3 for 1.8 × 10- 3mol/L.It is almost the same with surface tension method.
Traditional glyoxaline ion liquid is compared, bromination 1- methyl -3- dodecyl imidazole ([C12mim] Br), CMC is
9.7×10-3The CMC of mol/L, the glyoxaline ion liquid that the present invention obtains are considerably lower, have excellent surface-active.
Application examples 2:
In supramolecular chemistry application
According to beta-cyclodextrin: the molar ratio of ionic liquid is the ratio of 1:1, and beta-cyclodextrin is added to embodiment 3 and is obtained
Ionic liquid sample in, be diluted to aimed concn with deuterated water, be cooled to room temperature after being heated to clear solution, in Bruker
It is carried out on Avance-400 NMR spectrometer1H-1H 2D ROESY NMR two dimension hydrogen spectrometry.As a result as shown in Figure 5.Test knot
Fruit shows: the H-3 and H-5 of cyclodextrin inner chamber are produced with the adamantyl proton on ionic liquid significantly intersects peak, ring paste
Host -guest inclusion complex has occurred with adamantyl in essence, it was demonstrated that the adamantyl of ionic liquid forms Subjective and Objective by β-CD inclusion and surpasses
Molecule.And the ionic liquid of other traditional types such as [C12mim] Br is usually Long carbon chain inclusion in cyclodextrin inner chamber, display
The uniqueness of adamantane ionic liquid out.
Ratio by beta-cyclodextrin with molar ratio for 1:1 is added to the ionic liquid sample that embodiment 3 obtains, and is diluted with water
To after aimed concn, carried out on Zetasizer Nano-ZS90 nano particle size instrument and FEI-TECNAI G2-20 transmission electron microscope
Dynamic light scattering test and negative staining transmissioning electric mirror test.As a result as shown in Figure 6, Figure 7.Test result shows: simple ion
Liquid aqueous solution shows several nanometers of small micella, carries out after 1:1 matches and to form supermolecule with cyclodextrin, can institute's shape in water
At the vesica of diameter 150nm.
What has been described above is only a preferred embodiment of the present invention, it is noted that for those of ordinary skill in the art
For, under the premise of not departing from inventive concept, various modifications and improvements can be made, these belong to protection of the invention
Range.
Claims (10)
1. a kind of adamantyl glyoxaline ion liquid, chemical formula are as follows:
In formula, n=9 or 11；R is-CH2CH3Or-CH3。
2. a kind of preparation method of ionic liquid described in claim 1, steps are as follows:
(1) it is esterified: 1- adamantanecarboxylic acid, bromhydrin, catalyst and organic solvent being added in reaction vessel, are warming up to 80 DEG C
~120 DEG C of reaction 12h~for 24 hours, it removes solid impurity after reaction and solvent obtains crude product, crude product is after ethyl acetate dissolves
It is dry after saturated sodium carbonate, distillation washing, it crosses silicagel column and obtains 1- adamantanecarboxylic acid bromo Arrcostab after purification；
(2) quaternary ammoniated: 1- adamantanecarboxylic acid bromo Arrcostab and N- alkyl imidazole that the step (1) obtains are added to instead
It answers in container, and organic solvent is added and is uniformly mixed, in 50 DEG C~80 DEG C reaction for 24 hours~48h, remove solvent after reaction and obtain
To crude product, crude product is dried to obtain adamantyl glyoxaline ion liquid after recrystallization 1~3 time.
3. preparation method according to claim 2, it is characterised in that: bromhydrin described in step (1) is the bromo- 1- nonyl of 9-
One or two kinds of mixtures of the bromo- 1- undecyl alcohol of alcohol, 11-.
4. preparation method according to claim 2 or 3, it is characterised in that: step (1) 1- adamantanecarboxylic acid and bromhydrin
Molar ratio are as follows: 1:1~2.
5. preparation method according to claim 2, it is characterised in that: catalyst described in step (1) be butyl titanate,
The mixture of one or more of sulfamic acid, p-methyl benzenesulfonic acid.
6. preparation method according to claim 2 or 5, it is characterised in that: catalyst described in step (1) and 1- adamantane
The molar ratio of formic acid is 1:20~50.
7. preparation method according to claim 2, it is characterised in that: organic solvent described in step (1) is toluene, N, N-
The mixture of one or more of dimethylformamide, n-hexane.
8. preparation method according to claim 2, it is characterised in that: N- alkyl imidazole described in step (2) is N- methyl
Imidazoles or N- ethyl imidazol(e).
9. the preparation method according to claim 2 or 8, it is characterised in that: step (2) N- alkyl imidazole and 1- adamantane first
The molar ratio of sour bromo Arrcostab is 1:0.5~1.
10. a kind of ionic liquid described in claim 1 is in the application in surfactant or supramolecular chemistry field.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910287735.XA CN110041264A (en) | 2019-04-11 | 2019-04-11 | A kind of adamantyl glyoxaline ion liquid and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910287735.XA CN110041264A (en) | 2019-04-11 | 2019-04-11 | A kind of adamantyl glyoxaline ion liquid and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110041264A true CN110041264A (en) | 2019-07-23 |
Family
ID=67276782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910287735.XA Pending CN110041264A (en) | 2019-04-11 | 2019-04-11 | A kind of adamantyl glyoxaline ion liquid and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110041264A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113333020A (en) * | 2021-06-28 | 2021-09-03 | 沈阳工业大学 | Supermolecular onium salt catalyst for synthesizing carbonate and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992431A (en) * | 1973-09-24 | 1976-11-16 | Colgate-Palmolive Company | Quaternary compounds having anti-microbial activity |
| GB2010270A (en) * | 1977-12-16 | 1979-06-27 | Interx Research Corp | Novel "soft" anticholinergic agents exhibiting anti-secretory activity |
| CN103435506A (en) * | 2013-09-03 | 2013-12-11 | 天津民祥药业有限公司 | Preparation method of quaternary ammonium salt with adamantyl |
-
2019
- 2019-04-11 CN CN201910287735.XA patent/CN110041264A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992431A (en) * | 1973-09-24 | 1976-11-16 | Colgate-Palmolive Company | Quaternary compounds having anti-microbial activity |
| GB2010270A (en) * | 1977-12-16 | 1979-06-27 | Interx Research Corp | Novel "soft" anticholinergic agents exhibiting anti-secretory activity |
| CN103435506A (en) * | 2013-09-03 | 2013-12-11 | 天津民祥药业有限公司 | Preparation method of quaternary ammonium salt with adamantyl |
Non-Patent Citations (5)
| Title |
|---|
| JINGLIN SHEN等: "Self-assembled supramolecular hydrogel induced by -cyclodextrin and ionic liquid-type imidazolium gemini surfactant", 《COLLOIDS AND SURFACES A: PHYSICOCHEM. ENG. ASPECTS》 * |
| QIAN WANG等: "Supramolecular ternary polymer mediated by cucurbituril and cyclodextrin", 《POLYMER CHEMISTRY》 * |
| XING ZHONG等: "Aggregate morphology transition of an adamantane-containing surfactant via the host-guest interaction with β-cyclodextrin", 《JOURNAL OF MOLECULAR LIQUIDS》 * |
| YAN’AN GAO等: "Inclusion Complexes of -Cyclodextrin with Ionic Liquid Surfactants", 《J. PHYS. CHEM. B》 * |
| YIFENG HE: "Interaction between Ionic Liquids and -Cyclodextrin: A Discussion of Association Pattern", 《J. PHYS. CHEM. B》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113333020A (en) * | 2021-06-28 | 2021-09-03 | 沈阳工业大学 | Supermolecular onium salt catalyst for synthesizing carbonate and preparation method thereof |
| CN113333020B (en) * | 2021-06-28 | 2022-02-15 | 沈阳工业大学 | Supermolecular onium salt catalyst for synthesizing carbonate and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kuliszewska et al. | Gemini surfactants foam formation ability and foam stability depends on spacer length | |
| CN108524449B (en) | Near-infrared dye functionalized intelligent supramolecular vesicle loaded with medicine body | |
| Moutard et al. | Novel glycolipids based on cyclodextrins | |
| Zhang et al. | Synthesis and solvent enhanced relaxation property of water-soluble endohedral metallofullerenols | |
| CN105367687A (en) | Chitosan amphiphilic polymer surfactant, and synthetic method thereof | |
| CN112552311B (en) | Undoped organic small molecule hole transport material, perovskite solar cell and preparation method and application thereof | |
| Chen et al. | A rigid ringlike molecule: large second-order nonlinear optical performance, good temporal and thermal stability, and ideal spherical structure conforming to the “site isolation” principle | |
| CN110041264A (en) | A kind of adamantyl glyoxaline ion liquid and preparation method thereof | |
| CN112441965A (en) | Preparation method of nano assembly with AIE effect | |
| Fan et al. | Hydrogen-bond-driven supramolecular self-assembly of diacetylene derivatives for topochemical polymerization in solution | |
| EP3604313A1 (en) | Method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride | |
| Cui et al. | Solvent-tuned multiple self-assembly of a new sugar-appended gelator | |
| CN113046074B (en) | Method for synthesizing high-brightness fluorescent carbon quantum dots and application | |
| CN107674074B (en) | Preparation method and application of amphiphilic naphthalimide gelator | |
| Huang et al. | Mono-molecule-layer nano-ribbons formed by self-assembly of bolaamphiphiles | |
| UEKAMA et al. | Improvement of dissolution characteristics and chemical stability of prostaglandin E1 by γ-cyclodextrin complexation | |
| JP5294263B2 (en) | Dispersant for carbon nanotubes comprising dendrimer and method for dispersing carbon nanotubes using the same | |
| Prata et al. | Synthesis and molecular aggregation of new sugar bola-amphiphiles | |
| CN103467724B (en) | A kind of preparation method of fullerene polyester | |
| CN113896680A (en) | PH-responsive supramolecular nanotube monomer molecule and preparation method and application thereof | |
| CN113773338B (en) | Boron-containing organic free radical compound and preparation method and application thereof | |
| CN109836349B (en) | Adamantane-containing Gemini surfactant and synthesis method thereof | |
| CN114437171A (en) | Dipeptide surfactant containing azobenzene group and preparation method thereof | |
| CN103319397A (en) | Fullerene derivative micrometer flower and preparation method thereof | |
| CN107033152A (en) | A kind of poly phthalocyanine compound, organic field effect tube and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190723 |
|
| RJ01 | Rejection of invention patent application after publication |