CN108918490A - A kind of application of ionic liquid - Google Patents
A kind of application of ionic liquid Download PDFInfo
- Publication number
- CN108918490A CN108918490A CN201810775557.0A CN201810775557A CN108918490A CN 108918490 A CN108918490 A CN 108918490A CN 201810775557 A CN201810775557 A CN 201810775557A CN 108918490 A CN108918490 A CN 108918490A
- Authority
- CN
- China
- Prior art keywords
- ionic liquid
- fluorescence
- culture medium
- based sols
- spawn incubation
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The present invention relates to a kind of applications of ionic liquid, it includes the following steps：（a）Ionic liquid is respectively added in two different Spawn incubation based sols, a kind of Spawn incubation based sols are staphylococcus aureus culture medium solution, and another Spawn incubation based sols are Escherichia coli culture medium solution；The ionic liquid is the mixture selected from one of following general formula of the chemical structure or a variety of compositions；（b）By step（a）The Spawn incubation based sols of acquisition carry out fluorescence detection respectively at 254nm, compare its fluorescence intensity；Its type is determined according to the fluorescence intensity of Spawn incubation based sols：The higher Spawn incubation based sols of fluorescence intensity are the staphylococcus aureus culture medium solution.To realize the differentiation of different culture medium solution according to the fluorescence intensity of culture medium solution, the differentiation to species is realized.
Description
Technical field
The invention belongs to fluorescent material technical fields, and in particular to a kind of application of ionic liquid.
Background technique
In recent years, with the appearance of drug-resistant bacteria, the exploitation of antibacterial activity material causes the great attention of modern all circles.
Currently, the most widely used antibacterial agent of most study is cationic compound, cationic antibacterial agent has high efficiency, broad spectrum activity, life
The advantages that object compatibility height, small toxicity, is studied extensively, such as quaternary ammonium salt, pyridiniujm, imidazole salts.And bio-imaging, because of it
The advantages that high sensitivity, visibility are high, adjustability is strong, becomes the powerful in current biological study, wherein biological at
As detecting biomolecule because of its Noninvasive, a kind of simple unique method is provided to visualize the pattern details of bacterium, carefully
The metamorphosis of born of the same parents.Currently, most of bacterial cell imaging needs additional dyestuff to be dyed, and dyestuff is all generally high poison
Property and photo-labile, therefore develop a kind of new low toxicity, photostability material has very big researching value.
And most of luminescent material has good luminescent properties under solution state, aggregation then causes to quench.Therefore, gather
Collect the unique performance of induced luminescence (AIE) material and opens new window in fields such as chemical sensitisation, bio-sensing, biomarkers.
The fluorescence that the Chinese invention patent of Publication No. CN106039325A discloses a kind of bio-imaging in vivo and in vitro is raw
Physical prospecting needle and preparation method thereof.Its fluorescent bio-probes has loaded the nanoparticle of fluorescent chemicals, and nanoparticle includes tool
There are the fluorescent chemicals of aggregation-induced emission characteristic, wherein the fluorescent chemicals include that one or more aggregation-induced emissions are glimmering
Light blob, but the compound structure is complicated, preparation process is remarkable.The Chinese invention patent of Publication No. CN107001927A is public
Open it is a kind of for bacterium imaging aggregation-induced emission (AIE) compound synthesis method, although these can be used for cell bacterial without
Washing imaging, but bacterium cannot be accomplished to be killed.
Summary of the invention
A kind of application of ionic liquid is provided the invention aims to overcome the deficiencies in the prior art.
In order to solve the above technical problems, a kind of technical solution that the present invention takes is：A kind of application of ionic liquid, it is wrapped
Include following steps：
(a) ionic liquid is respectively added in two different Spawn incubation based sols, a kind of bacterium culture medium
Solution is staphylococcus aureus culture medium solution, and another Spawn incubation based sols are Escherichia coli culture medium solution；It is described
Ionic liquid is the mixture selected from one of following general formula of the chemical structure or a variety of compositions：
In formula, the integer that n is 0~6, X Cl, Br, I, BF4、PF6 -And R1COO-One of, R and R1Independently of each other
The alkyl for being 1~8 for carbon atom number；
(b) the Spawn incubation based sols for obtaining step (a) carry out fluorescence detection respectively at 254nm, and it is strong to compare its fluorescence
Degree；Its type is determined according to the fluorescence intensity of Spawn incubation based sols：The higher Spawn incubation based sols of fluorescence intensity are described
Staphylococcus aureus culture medium solution.
Optimally, R is straight chained alkyl, carbon atom number 1,4 or 8.
Optimally, R1The alkyl for being 1~3 for carbon atom number.
The invention has the beneficial effects that：The application of ionic liquid of the present invention, by using the ionic liquid of specific structure
Body is mixed with staphylococcus aureus culture medium solution, Escherichia coli culture medium solution respectively, thus molten according to culture medium
The fluorescence intensity of liquid realizes the differentiation of different culture medium solution, realizes the differentiation to species.
Detailed description of the invention
Fig. 1 is fluorescence intensity comparison diagram of the sterilization fluorescence ionic liquid in different solvents in embodiment 2；
Fig. 2 is fluorescence intensity comparison diagram of the sterilization fluorescence ionic liquid in different solvents in embodiment 3；
Fig. 3 is fluorescence intensity comparison diagram of the sterilization fluorescence ionic liquid in different solvents in embodiment 4；
Fig. 4 is that fluorescence ionic liquid is sterilized in embodiment 2 to the fluorogram of staphylococcus aureus LB culture medium solution；
Fig. 5 is that fluorescence ionic liquid is sterilized in embodiment 2 to the fluorogram of Escherichia coli LB culture medium solution；
Fig. 6 is that fluorescence ionic liquid is sterilized in embodiment 3 to the fluorogram of staphylococcus aureus LB culture medium solution；
Fig. 7 is that fluorescence ionic liquid is sterilized in embodiment 3 to the fluorogram of Escherichia coli LB culture medium solution；
Fig. 8 is that fluorescence ionic liquid is sterilized in embodiment 4 to the fluorogram of staphylococcus aureus LB culture medium solution；
Fig. 9 is that fluorescence ionic liquid is sterilized in embodiment 4 to the fluorogram of Escherichia coli LB culture medium solution；
Figure 10 is the nuclear magnetic spectrogram that fluorescence ionic liquid is sterilized in embodiment 2；
Figure 11 is the nuclear magnetic spectrogram that fluorescence ionic liquid is sterilized in embodiment 3；
Figure 12 is the nuclear magnetic spectrogram that fluorescence ionic liquid is sterilized in embodiment 4；
Figure 13 is the antibacterial control that various concentration sterilizes fluorescence ionic liquid to staphylococcus aureus in embodiment 2
Figure；
Figure 14 is that various concentration sterilizes fluorescence ionic liquid to the antibacterial comparative diagram of Escherichia coli in embodiment 2；
Figure 15 is the antibacterial control that various concentration sterilizes fluorescence ionic liquid to staphylococcus aureus in embodiment 3
Figure；
Figure 16 is that various concentration sterilizes fluorescence ionic liquid to the antibacterial comparative diagram of Escherichia coli in embodiment 3；
Figure 17 is the antibacterial control that various concentration sterilizes fluorescence ionic liquid to staphylococcus aureus in embodiment 4
Figure；
Figure 18 is that various concentration sterilizes fluorescence ionic liquid to the antibacterial comparative diagram of Escherichia coli in embodiment 4.
Specific embodiment
The application of ionic liquid of the present invention, it includes the following steps：(a) ionic liquid is respectively added to two different
In Spawn incubation based sols, a kind of Spawn incubation based sols are staphylococcus aureus culture medium solution, another strain
Culture medium solution is Escherichia coli culture medium solution；The ionic liquid is selected from one of following general formula of the chemical structure or more
The mixture of kind composition：
In formula, the integer that n is 0~6, X Cl, Br, I, BF4、PF6 -And R1COO-One of, R and R1Independently of each other
The alkyl for being 1~8 for carbon atom number；(b) the Spawn incubation based sols for obtaining step (a) carry out fluorescence inspection respectively at 254nm
It surveys, compares its fluorescence intensity；Its type is determined according to the fluorescence intensity of Spawn incubation based sols：The higher strain training of fluorescence intensity
Supporting based sols is the staphylococcus aureus culture medium solution.To realize different trainings according to the fluorescence intensity of culture medium solution
The differentiation for supporting based sols, realizes the differentiation to species.R is straight chained alkyl, carbon atom number 1,4 or 8.R1For carbon original
The alkyl that subnumber is 1~3.By carrying out specific structure design to ionic liquid, not only still with significant bactericidal effect, and
And also with the characteristic of aggregation-induced emission, to realize without the imaging of washing bacterium and be used for bacterium imaging；By adjusting difference
The adjusting of different fluorescence phenomenons may be implemented to realize the adjusting to anti-microbial property in the alkyl chain of chain length.R is usually straight
Alkyl group, carbon atom number are preferably 1,4 or 8.R1The alkyl for being 1~3 for carbon atom number, usually methyl, ethyl, propyl and
Isopropyl.
The preparation method of above-mentioned sterilization fluorescence ionic liquid, it includes the following steps：Crown ether derivative is had with nitrogenous
Machine object, which is dissolved in easy volatile solvent, to be stirred to react, and crude product is evaporated in vacuo to obtain, and is then washed repeatedly with ether up to product；
The molar ratio of the crown ether derivative and itrogenous organic substance is 1：4.05~4.1；The chemical structural formula of the crown ether derivative isY is Cl, Br or I；The chemical structural formula of the itrogenous organic substance is The easy volatile solvent is chloroform, dichloroethanes, methanol or ethyl alcohol.When X is BF4、PF6 -And R1COO-In one
Kind when, further preferably product dissolution is placed in hydroxide ion exchanger resin and carries out ion exchange, then with it is corresponding
Salt or acid reaction, are spin-dried for being washed with water repeatedly.
The preferred embodiment of the invention is described in detail below in conjunction with attached drawing：
Embodiment 1
The present embodiment provides the preparation methods of crown ether derivative (TPE-Br) a kind of, specially：
(a)(TPE-OMe) synthesis：Zinc powder (2.7g) is added to dissolved with 4,4- dimethoxy
In the anhydrous tetrahydro furan of benzophenone (2.0g) (40ml), it is placed in cooling in ice-water bath, in a nitrogen environment, uses syringe
(3.5ml is stirred continuously slow addition titanium tetrachloride, is transferred in 66 DEG C of oil bath pan after being added dropwise, and is heated to reflux 16 hours；
10% solution of potassium carbonate (mass fraction) quenching reaction is added, obtains blackish green oily liquids；It is purified by silica gel column chromatography to obtain
TPE-OMe(0.97g；42%)；1H NMR(d6-DMSO,400MHz,δ):6.83-6.85(d,8H),6.67-6.69(d,8H),
3.67(s,12H)；
(b)(TPE-OH) synthesis：The anhydrous methylene chloride of TPE-OMe (2.0g) is added
(40ml) solution is placed in cooling in ice-water bath, in a nitrogen environment, injects Boron tribromide (1.7ml), and it is small that 2 are stirred in ice-water bath
Shi Hou continues stirring 16 hours at room temperature；After reaction, deionized water is added dropwise in ice-water bath makes its hydrolysis, observes
There is violet solid precipitation.Filtering, washing weigh (1.40g, 80%) after dry；1H NMR(d6-DMSO,400MHz,δ):
6.69-6.71(d,8H),6.46-6.48(d,8H),3.37(s,4H)；
(c)Synthesis (TPE-Br)：By 18- crown ether -6 (0.1g) and potassium carbonate
(1.92g) is added in acetonitrile (25ml) solution dissolved with TPE-OH (0.5g), is placed in 70 DEG C of oil bath pans and is stirred.In nitrogen atmosphere
It under enclosing, is added dropwise Isosorbide-5-Nitrae-dibromobutane (6.0g), reacts 12 hours.Filtering, takes filtrate to rotate, obtains yellow solution.Silica gel column layer
Analysis purifying obtains TPE-Br, weighs to obtain 0.4g, yield 35%.1H NMR(d6-DMSO,400MHz,δ):6.82-6.84(d,8H),
6.67-6.69(d,8H),3.91(m,8H),3.59(m,8H),1.935(m,8H),1.786(m,8H)。
Embodiment 2
The present embodiment provides a kind of preparation methods for sterilizing fluorescence ionic liquid, include the following steps：By TPE-Br
With 1- methylimidazole with 1：4.05 molar ratio is dissolved in chloroform, and stirring at normal temperature is for 24 hours；Subsequent mixture evaporated in vacuo,
Crude product is obtained, is washed three times with ether to remove remaining 1- methylimidazole, obtains yellow, viscous liquid(i.e. TPE-C1Im),1H NMR(400MHz,d6-DMSO,δ):9.118(s,
4H),7.774(s,4H),7.708(s,4H),6.848-6.814(d,8H),6.695-6.643(d,8H),4.235-4.170
(m, 8H), 3.929-3.878 (m, 8H), 3.604-3.542 (m, 12H), 1.827-1.739 (m, 8H) (such as Figure 10), not
Fluorescence intensity comparison in good solvent water and good solvent ethyl alcohol is as shown in Figure 1.
Embodiment 3
The present embodiment provides a kind of preparation method for sterilizing fluorescence ionic liquid, in it and embodiment 2
It is almost the same, unlike：TPE-Br and 1- butyl imidazole is reacted, yellow, viscous liquid is obtained(i.e. TPE-C4Im),1H NMR(d6-DMSO,400MHz,δ):9.287
(s,4H),7.829(s,8H),6.830-6.813(d,8H),6.688-6.668(d,8H),4.225-4.170(m,16H),
3.962-3.900(m,8H),1.996-1.861(m,8H),1.672-1.650(m,8H),1.311-1.162(m,16H),
0.908-0.855 (m, 12H) (such as Figure 11), the fluorescence intensity in poor solvent water and good solvent ethyl alcohol are compared such as Fig. 2 institute
Show.
Embodiment 4
The present embodiment provides a kind of preparation method for sterilizing fluorescence ionic liquid, in it and embodiment 2
It is almost the same, unlike：TPE-Br and 1- octylimidazole is reacted, yellow, viscous liquid is obtained(i.e. TPE-C8Im),1H NMR(d6-DMSO,400MHz,
δ):9.274(s,4H),7.828(s,8H),6.830-6.809(d,8H),6.680-6.660(d,8H),4.240-4.140(m,
16H),3.946-3.830(m,8H),1.970-1.870(m,8H),1.857-1.780(m,8H),1.690-1.580(m,8H),
1.330-1.125 (m, 40H), 0.849-0.835 (m, 12H) (such as Figure 12), in poor solvent water and good solvent ethyl alcohol
Fluorescence intensity comparison is as shown in Figure 3.Fluorescence intensity of the sterilization fluorescence ionic liquid in poor solvent in embodiment 2-4 compared with
It is close, but in good solvent ethyl alcohol；Fluorescence intensity in this example is significantly greater than in embodiment 2 and embodiment 3.
Embodiment 5
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2, no
Be：TPE-Br and methylpyrrole are reacted, yellow, viscous liquid is obtained
(i.e. TPE-C1Py),1H NMR(400MHz,d6-DMSO,δ):7.462-7.438(d,8H),6.931-6.915(d,8H),
4.064-4.033(m,8H),3.318(s,12H),3.225-3.189(m,24H),1.754-1.719(m,32H)。
Embodiment 6
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
Unlike：TPE-Br and butyl pyrroles are reacted, yellow, viscous liquid is obtained
(i.e. TPE-C4Py),1H NMR(400MHz,d6-DMSO,δ):7.467-7.443(d,8H),6.953-6.934(d,8H),
4.075-4.056(m,8H),3.327-3.275(m,32H),1.753-1.714(m,40H),1.318-1.304(m,8H),
0.893-0.871(m,12H)。
Embodiment 7
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
Unlike：TPE-Br and octyl pyrroles are reacted, yellow, viscous liquid is obtained
(i.e. TPE-C8Py),1H NMR(400MHz,d6-DMSO,δ):7.541-7.493(d,8H),6.975-6.962(d,8H),
4.062-4.045(m,8H),3.315-3.246(m,32H),1.764-1.723(m,40H),1.292-1.268(m,40H),
0.877-0.856(m,12H).Fluorescence intensity in this example is also significantly greater than in embodiment 5 and embodiment 6.
Embodiment 8
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, sodium hexafluoro phosphate water is added dropwise
Half an hour is stirred at room temperature in solution, generates yellow mercury oxide, and solution vacuum is spin-dried for, is washed repeatedly with methanol, and obtaining anion is PF6 -
Ionic liquid
Embodiment 9
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, sodium tetrafluoroborate water is added dropwise
Half an hour is stirred at room temperature in solution, generates yellow mercury oxide, and solution vacuum is spin-dried for, is washed repeatedly with methanol, and obtaining anion is BF4 -
Ionic liquid
Embodiment 10
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, is exchanged in hydroxide ion
By Br in resin-It is exchanged into OH-, 8h then is stirred at room temperature with acetic acid in aqueous solution；Solution vacuum is spin-dried for, and is washed with water repeatedly,
Obtaining anion is CH3COO-Ionic liquid
Embodiment 11
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 2,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, is exchanged in hydroxide ion
By Br in resin-It is exchanged into OH-, 8h then is stirred at room temperature with benzoic acid in aqueous solution；Solution vacuum is spin-dried for, and is washed with water repeatedly
It washs, obtaining anion is CH3COO-Ionic liquid
Embodiment 12
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 5,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, it is water-soluble that sodium hexafluoro phosphate is added dropwise
Half an hour is stirred at room temperature in liquid.Yellow mercury oxide is generated, solution vacuum is spin-dried for, is washed repeatedly with methanol, and obtaining anion is PF6 -'s
Ionic liquid
Embodiment 13
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 5,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, it is water-soluble that sodium tetrafluoroborate is added dropwise
Half an hour is stirred at room temperature in liquid.Yellow mercury oxide is generated, solution vacuum is spin-dried for, is washed repeatedly with methanol, and obtaining anion is BF4 -'s
Ionic liquid
Embodiment 14
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 5,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, exchanges and set in hydroxide ion
By Br in rouge-It is exchanged into OH-, 8h then is stirred at room temperature with acetic acid in aqueous solution；Solution vacuum is spin-dried for, and is washed with water repeatedly, is obtained
It is CH to anion3COO-Ionic liquid
Embodiment 15
The present embodiment provides it is a kind of sterilize fluorescence ionic liquid preparation method, it with it is almost the same in embodiment 5,
The difference is that also following the steps below：
By 0.01gIt is dissolved in 5mL methanol, exchanges and set in hydroxide ion
By Br in rouge-It is exchanged into OH-, 8h then is stirred at room temperature with acetic acid in aqueous solution；Solution vacuum is spin-dried for, and is washed with water repeatedly, is obtained
It is CH to anion3COO-Ionic liquid
Embodiment 16
The present embodiment provides a kind of applications of above-mentioned sterilization fluorescence ionic liquid, specially：It will be made from embodiment 2-4
Sterilize fluorescence ionic liquid (10-4M) be respectively added to containing staphylococcus aureus, Escherichia coli LB culture medium solution in
(OD600=0.2), fluorescence detection is carried out in 254nm；Wherein, fluorescence ionic liquid is sterilized in embodiment 2 to golden yellow grape
Coccus, the fluorescence difference of Escherichia coli are as shown in Figure 4 and Figure 5, it is seen that the fluorescence before and after addition sterilization fluorescence ionic liquid
Intensity has significant change, but the front and back fluorescence intensity change after ionic liquid is added in staphylococcus aureus culture medium more
Greatly；It is also identical that change in fluorescence trend caused by fluorescence ionic liquid is sterilized in same embodiment 3, as shown in Figure 6 and Figure 7；It is real
It is as shown in Figure 8 and Figure 9 to the fluorescence difference of staphylococcus aureus, Escherichia coli to apply sterilization fluorescence ionic liquid in example 4,
Its (see Fig. 9) poor to the responsiveness of Escherichia coli；Fluorescence ionic liquid in embodiment 5-7 is added to containing golden yellow
Staphylococcus, Escherichia coli LB culture medium solution in (OD600=0.2) fluorescence detection, result and implementation, are carried out in 254nm
Trend in example 2-4 is consistent, the difference is that antibiotic property and fluorescence intensity are slightly weak；And after embodiment 8-15 is then anion exchange
Fluorescence ionic liquid, it is almost the same with the antibiotic property of the fluorescence ionic liquid before ion exchange, unlike when yin from
When son is acetate, fluorescence intensity enhancing.Fluorescence ionic liquid solution will be also sterilized made from embodiment 2-4 simultaneously
The LB culture medium solution of (0.25mg/ml~0.0625mg/ml) respectively with staphylococcus aureus, Escherichia coli mixes in equal volume
It closes, cultivates 4h in 37 DEG C of constant incubator；It takes 10 μ L mixed solution even spreads on a lbmc agar plate, and is cultivated at 37 DEG C
12h counts bacterium colony, and calculates antibiotic rate of the sample relative to control group.Fluorescence ionic liquid pair is wherein sterilized in embodiment 2
Staphylococcus aureus, the antibacterial effect difference of Escherichia coli are as shown in Figure 13 and Figure 14, it is seen that sterilization fluorescence ionic liquid
Anti-microbial property it is significant；The anti-microbial property that fluorescence ionic liquid is sterilized in same embodiment 3 is also excellent, such as Figure 15 and Figure 16 institute
Show；Fluorescence ionic liquid is sterilized in embodiment 4 to the antibiotic property of staphylococcus aureus, Escherichia coli respectively such as Figure 17 and figure
Shown in 18.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention.It is all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (3)
1. a kind of application of ionic liquid, which is characterized in that it includes the following steps：
(a) ionic liquid is respectively added in two different Spawn incubation based sols, a kind of Spawn incubation based sols
For staphylococcus aureus culture medium solution, another Spawn incubation based sols are Escherichia coli culture medium solution；The ion
Liquid is the mixture selected from one of following general formula of the chemical structure or a variety of compositions：
In formula, the integer that n is 0~6, X Cl, Br, I, BF4、PF6 -And R1COO-One of, R and R1Independently of one another carbon
The alkyl that atomicity is 1~8；
(b) the Spawn incubation based sols for obtaining step (a) carry out fluorescence detection respectively at 254nm, compare its fluorescence intensity；Root
Its type is determined according to the fluorescence intensity of Spawn incubation based sols：The higher Spawn incubation based sols of fluorescence intensity are the golden yellow
Aureus culture medium solution.
2. the application of ionic liquid according to claim 1, it is characterised in that：R is straight chained alkyl, carbon atom number 1,4
Or 8.
3. the application of ionic liquid according to claim 1, it is characterised in that：R1The alkyl for being 1~3 for carbon atom number.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810775557.0A CN108918490A (en) | 2018-07-16 | 2018-07-16 | A kind of application of ionic liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810775557.0A CN108918490A (en) | 2018-07-16 | 2018-07-16 | A kind of application of ionic liquid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108918490A true CN108918490A (en) | 2018-11-30 |
Family
ID=64415091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810775557.0A Pending CN108918490A (en) | 2018-07-16 | 2018-07-16 | A kind of application of ionic liquid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108918490A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7387155B2 (en) | 2019-11-21 | 2023-11-28 | 国立研究開発法人物質・材料研究機構 | ionic liquid |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104224776A (en) * | 2014-08-29 | 2014-12-24 | 国家纳米科学中心 | Application of tetraphenyl ethylene derivative in preparation of antibacterial agent |
| CN104592272A (en) * | 2015-02-26 | 2015-05-06 | 天津师范大学 | Cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex used as potential fluorescent material and preparation method of cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex |
| CN104749377A (en) * | 2015-03-12 | 2015-07-01 | 浙江大学 | Fluorescent probe with aggregation-induced luminescent property and preparation method and application of fluorescent probe |
| CN106518730A (en) * | 2016-10-27 | 2017-03-22 | 武汉大学 | Zwitterion modified tetraphenylethylene, preparation method and application thereof |
| CN108101781A (en) * | 2016-11-25 | 2018-06-01 | 国家纳米科学中心 | A kind of antimicrobial molecule based on tetraphenyl ethylene and its preparation method and application |
| CN108849908A (en) * | 2018-07-16 | 2018-11-23 | 苏州大学 | A kind of sterilization fluorescence ionic liquid and preparation method thereof |
-
2018
- 2018-07-16 CN CN201810775557.0A patent/CN108918490A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104224776A (en) * | 2014-08-29 | 2014-12-24 | 国家纳米科学中心 | Application of tetraphenyl ethylene derivative in preparation of antibacterial agent |
| CN104592272A (en) * | 2015-02-26 | 2015-05-06 | 天津师范大学 | Cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex used as potential fluorescent material and preparation method of cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex |
| CN104749377A (en) * | 2015-03-12 | 2015-07-01 | 浙江大学 | Fluorescent probe with aggregation-induced luminescent property and preparation method and application of fluorescent probe |
| CN106518730A (en) * | 2016-10-27 | 2017-03-22 | 武汉大学 | Zwitterion modified tetraphenylethylene, preparation method and application thereof |
| CN108101781A (en) * | 2016-11-25 | 2018-06-01 | 国家纳米科学中心 | A kind of antimicrobial molecule based on tetraphenyl ethylene and its preparation method and application |
| CN108849908A (en) * | 2018-07-16 | 2018-11-23 | 苏州大学 | A kind of sterilization fluorescence ionic liquid and preparation method thereof |
Non-Patent Citations (5)
| Title |
|---|
| YAMIN LI ET AL.: "Polyion complex micellar nanoparticles for integrated fluorometric detection and bacteria inhibition in aqueous media", 《BIOMATERIALS》 * |
| 叶朝辉: "《武汉光电论坛系列文集（第四辑）》", 31 December 2017 * |
| 商成杰: "《新型染整助剂手册》", 31 October 2002, 中国纺织出版社 * |
| 张文选 等: "《全国基层卫生人员合理用药知识培训教材》", 31 October 2012 * |
| 杜斌 等: "四苯基乙烯类化合物在荧光传感领域的研究进展", 《材料导报A：综述篇》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7387155B2 (en) | 2019-11-21 | 2023-11-28 | 国立研究開発法人物質・材料研究機構 | ionic liquid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107602598B (en) | A kind of application on Zn, Tb different metal base organic crystalline material, preparation method and its sensing identification antibiotic | |
| CN110117488B (en) | Near-infrared antibiotic fluorescent probe detection reagent, preparation method and application thereof | |
| CN110950779B (en) | Photosensitizer integrating bacterial fluorescence imaging and photodynamic sterilization and preparation method and application thereof | |
| CN108849908A (en) | A kind of sterilization fluorescence ionic liquid and preparation method thereof | |
| CN108752401B (en) | Bactericidal material containing BODIPY and preparation method and application thereof | |
| CN111574525A (en) | Metalloporphyrin complex, preparation method and application | |
| CN102643297B (en) | Antibacterial copper ternary complex with fluorescence and preparation method and application thereof | |
| Li et al. | A water-soluble fluorescent chemosensor having a high affinity and sensitivity for Zn2+ and its biological application | |
| CN105001193A (en) | Cationic water-soluble oligothiophene acetylene compound, and preparation method and application thereof | |
| CN104830318B (en) | A kind of fluorescent tag molecule of high state of aggregation fluorescent emission and preparation method thereof | |
| CN108918490A (en) | A kind of application of ionic liquid | |
| CN112159522A (en) | Water-soluble rhodamine-based fluorescent/colorimetric dual-mode probe and preparation method and application thereof | |
| CN110642882A (en) | Fluorescent probe with hydrogen peroxide detection and photodynamic cancer cell killing activity as well as preparation method and application thereof | |
| CN102060866B (en) | Rare earth ternary complex as well as preparation method and application thereof | |
| CN113712043A (en) | Graphene composite system water-based bactericidal disinfectant and preparation method thereof | |
| CN110407873B (en) | Tumor microenvironment H2O2Response crosslinking near-infrared molecular probe and application thereof | |
| CN108467475A (en) | A kind of cyclic polymer and its preparation method and application | |
| CN108250211A (en) | One kind is used to detect Zn2+Fluorescence probe and preparation method thereof | |
| CN102659547B (en) | Ophiobolin sesterterpene compound and preparation and application thereof | |
| CN109678986A (en) | A kind of rutin chelate and its preparation method and application | |
| CN116396497B (en) | Metal organic framework material, ligand structure thereof and application of metal organic framework material in nano enzyme | |
| CN111187226B (en) | Compound for specifically killing gram-negative bacteria, preparation method and application | |
| CN109942504B (en) | Fluorescent probe molecule for detecting hypochlorous acid and preparation method thereof | |
| CN102584871A (en) | Rare earth coordination compound containing Schiff base and bipyridyl and preparation method and bacteriostasis application thereof | |
| CN110003448A (en) | Conjugated polymer and its preparation method and application with aggregation-induced emission property |
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: 20181130 |
|
| RJ01 | Rejection of invention patent application after publication |