CN109777397A - A kind of fluorescence vesica and preparation method thereof - Google Patents
A kind of fluorescence vesica and preparation method thereof Download PDFInfo
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- CN109777397A CN109777397A CN201910018350.3A CN201910018350A CN109777397A CN 109777397 A CN109777397 A CN 109777397A CN 201910018350 A CN201910018350 A CN 201910018350A CN 109777397 A CN109777397 A CN 109777397A
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Abstract
The invention discloses a kind of fluorescence vesicas and preparation method thereof.Method is as follows: (1) using triethylene glycol monomethyl ether, paratoluensulfonyl chloride and methylene chloride as raw material, being prepared into glassy yellow grease Me-TEG-Ts；(2) using Me-TEG-Ts, gallicin, potassium iodide, potassium carbonate and anhydrous n,N-Dimethylformamide as raw material, it is prepared into an oily liquid, column is crossed with the methylene chloride/methanol mixed liquor of volume ratio 30:1 and obtains compound A；(3) using hydrazine hydrate, compound A and ethyl alcohol as raw material, it is prepared into oily compound B；(4) with compound B, pyrene formaldehyde, tetrahydrofuran and ethanol raw material, it is prepared into compound G；(5) compound G is soluble in water, compound G aqueous solution is obtained, compound G aqueous solution is drawn and instills in water, fluorescence vesica is obtained after standing.The characteristics of vesica of the invention is a kind of new structural vesica, has preparation process simple, unstressed configuration agent, and fluorescence intensity is stablized, good compatibility.
Description
Technical field
The present invention relates to a kind of vesica and preparation method thereof, especially a kind of fluorescence vesica and preparation method thereof.
Background technique
Polymer vesicle is orderly assembled by amphipathic nature block polymer, and typical polymer vesicle is by closed double
The spherical shape or elliposoidal structure of the hydrophilic core composition of tunic and duplicature package.Form the block copolymerization species of polymer vesicle
Amphipathy macromolecule compound that is various, predominantly synthesizing, it is amphipathic be suitable for, to be gathered into single polymer layer capsule
Bubble.Now current polymer vesicle is mainly used for containing drug: such as hydrophilic chemistries drug, enzyme, albumen and polypeptide, DNA or RNA
Deng can be dissolved in its hydrophilic core, and hydrophobic drug then can be by solubilising in duplicature hydrophobic inner core.In recent years, more
The appearance of kind stimulation sensitive material, imparts a variety of stimulation sensibility of polymer vesicle, so that it is in terms of the release of drug
It is more controllable.Polymer vesicle can be avoided drug by the destruction of internal pH and enzyme environment, extend drug as pharmaceutical carrier
Residence time in vivo shows huge application potential in field of medicaments to achieve the purpose that long-acting.
Especially bio-imaging and in terms of, fluorescence vesica have very good application prospect, system
Preparation Method also multimodal multiplicity, but the preparation process of most of fluorescence vesicas is complex, the fluorescent dye introduced in preparation process
For organism or adversely affect.Therefore, design it is a kind of simple, do not add the method for fluorescer and have to prepare fluorescence vesica
Highly important scientific research value and industrial significance.
Summary of the invention
The object of the present invention is to provide a kind of fluorescence vesicas and preparation method thereof.Vesica of the invention is a kind of novel
The characteristics of vesica of structure has preparation process simple, unstressed configuration agent, and fluorescence intensity is stablized, good compatibility.
Technical solution of the present invention: a kind of fluorescence vesica, chemical structural formula are as shown in Fig. 3.
A kind of preparation method of fluorescence vesica according to claim 1, includes the following steps:
(1) using triethylene glycol monomethyl ether, paratoluensulfonyl chloride and methylene chloride as raw material, raw material is mixed and is made it dissolve,
Then it is in atropurpureus that sodium hydroxide solution is added dropwise under ice bath stirring and is examined to solution with pH test paper, is stirred to react under room temperature, then
Filter is washed with water, lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, and dilute sodium hydroxide is added
Solution is stirred to react, and liquid separation, water layer is washed with methylene chloride, is then combined with organic phase, is washed with water, then uses saturated sodium chloride solution
It washes, dry with anhydrous sodium sulfate, liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-TEG-Ts；
It (2) is original with Me-TEG-Ts, gallicin, potassium iodide, potassium carbonate and anhydrous n,N-Dimethylformamide
Material, reacts 50-70 hours at 70-90 DEG C after raw material is mixed, and rotary evaporation of solvent washs solid with methylene chloride, washing
Liquid is washed with saturated sodium bicarbonate solution, then is washed with saturated common salt, and rotary evaporation organic solvent obtains an oily liquid, uses volume ratio
The methylene chloride/methanol mixed liquor of 30:1 crosses column and obtains compound A；
(3) it using hydrazine hydrate, compound A and ethyl alcohol as raw material, is reacted 2.5-3.5 days at 60-80 DEG C after raw material is mixed,
It is extracted with dichloromethane after rotary evaporation concentration, dichloromethane extract is washed with water, then is washed with saturated common salt, organic phase nothing
Aqueous sodium persulfate is dry, and rotary evaporation of solvent obtains oily compound B；
(4) it with compound B, pyrene formaldehyde, tetrahydrofuran and ethanol raw material, is reacted at 80-100 DEG C after raw material is mixed
30-40 hours, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, and centrifugation repeats
Compound G；
(5) compound G is soluble in water, compound G aqueous solution is obtained, compound G aqueous solution is drawn and instills in water, after standing
Obtain fluorescence vesica.
The preparation method of fluorescence vesica above-mentioned, the specific steps are as follows:
(1) 50-70g triethylene glycol monomethyl ether, 100-120g paratoluensulfonyl chloride and 550-650ml methylene chloride are mixed
It makes it dissolve, it is in atropurpureus that sodium hydroxide solution is then added dropwise under ice bath stirring and is examined to solution with pH test paper, is stirred under room temperature
Filter is washed with water in 10-15h, and lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, is added dilute
Sodium hydroxide solution stirs 10-15h, liquid separation, and water layer is washed 1-3 times with methylene chloride, is then combined with organic phase, is washed with water 2-4 times,
It is washed 1-3 times with saturated sodium chloride solution again, dry with anhydrous sodium sulfate, liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-
TEG-Ts；
(2) 50-60gMe-TEG-Ts, 7.5-8.5g gallicin, 5-6g potassium iodide and 55-65g potassium carbonate are added
Enter in anhydrous n,N-Dimethylformamide, is reacted 50-70 hours at 70-90 DEG C, rotary evaporation of solvent is washed with methylene chloride
Solid 1-3 times, cleaning solution are washed 2-4 times with saturated sodium bicarbonate solution, then are washed 2-4 times with saturated common salt, and rotary evaporation is organic
Solvent obtains an oily liquid, crosses column with the methylene chloride/methanol mixed liquor of volume ratio 30:1 and obtains compound A；
(3) 2.5- is reacted at 60-80 DEG C after mixing 40-60ml hydrazine hydrate, 3-4g compound A and 90-110ml ethyl alcohol
It 3.5 days, is extracted with dichloromethane after rotary evaporation concentration, dichloromethane extract is washed with water 2-4 times, then is washed with saturated common salt
2-4 times, organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains oily compound B；
(4) in 80- after 1-2g compound B, 0.1-1g pyrene formaldehyde, 15-25ml tetrahydrofuran and 30-35ml ethyl alcohol being mixed
It is reacted 30-40 hours at 100 DEG C, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating,
Centrifugation repeats 2-4 times to obtain compound G；
(5) 35-45mg compound G is dissolved in 3-7ml water, obtains compound G aqueous solution, draw 20-40 μ l compound G water
Solution instills in 2-4ml water, obtains fluorescence vesica after standing 1-10 minutes.
The preparation method of fluorescence vesica above-mentioned is by 60g triethylene glycol monomethyl ether, 108g to first in the step (1)
Benzene sulfonyl chloride and the mixing of 600ml methylene chloride.
The preparation method of fluorescence vesica above-mentioned is by 55gMe-TEG-Ts, 7.93g gallic acid in the step (2)
Methyl esters, 5.59g potassium iodide and 59.8g potassium carbonate are added in anhydrous n,N-Dimethylformamide.
The preparation method of fluorescence vesica above-mentioned, in the step (3), be by 50ml hydrazine hydrate, 3.5g compound A and
The mixing of 100ml ethyl alcohol.
The preparation method of fluorescence vesica above-mentioned, in the step (4), be by 1.4g compound B, 0.5g pyrene formaldehyde,
18ml tetrahydrofuran and the mixing of 32ml ethyl alcohol.
The preparation method of fluorescence vesica above-mentioned is that 41.75mg compound G is dissolved in 5ml water in the step (5),
Obtaining concentration is 1*10-2Then the compound G aqueous solution of mol/L takes 30 μ l compound G aqueous solutions to instill in 3ml water, stand 1-10
Fluorescence vesica is obtained after minute.
Beneficial effects of the present invention
1, fluorescence vesica construction method of the present invention is simple, easily implements.
2, fluorescer is not added in fluorescence vesica manufacturing process of the present invention, had no adverse effect to organism.
3, there is the molecular structure stabilized of fluorescence vesica of the present invention fluorescence intensity to stablize, not weak for a long time.
4, fluorescence imitated vesicle structure of the present invention is peculiar, has double membrane structure, has good compatibility with biomembrane.
Detailed description of the invention
Fig. 1 is fluorescence vesica transmission electron microscope (TEM) image produced by the present invention；
Fig. 2 is the fluorescence picture under fluorescence vesica fluorescence spectra produced by the present invention and ultraviolet lamp 365nm wavelength illumination；
Fig. 3 is the schematic arrangement of fluorescence vesica of the present invention；
Fig. 4 is the synthetic schemes of fluorescence vesica of the present invention.
Specific embodiment
Below with reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1:
(1) 60g triethylene glycol monomethyl ether and 108g paratoluensulfonyl chloride are weighed in 1000ml flask, 600ml bis- is added
Chloromethanes dissolves, and sodium hydroxide solution is added dropwise under ice bath stirring, and (72g sodium hydroxide is dissolved in water, and solution is examined with pH test paper in purple
Black, pH=12), 12h is stirred under room temperature, filter is washed with water, lower layer's organic phase is dry with anhydrous sodium sulfate, rotary evaporation of solvent
Glassy yellow grease is obtained, diluted sodium hydroxide solution is added and stirs 12h, liquid separation, water layer is washed twice with methylene chloride, merged organic
Phase is washed with water 3 times, then washed twice with saturated sodium-chloride liquid, and anhydrous sodium sulfate is dry, and liquid separation rotary evaporation of solvent obtains glassy yellow oil
Shape object Me-TEG-Ts；
(2) 55gMe-TEG-Ts, 7.93g gallicin, 5.59g potassium iodide, 59.8g potassium carbonate are weighed in 1000ml
In flask, anhydrous n,N-Dimethylformamide is added, is reacted 60 hours at 80 DEG C, is spin-dried for, washs solid three times with methylene chloride,
Cleaning solution is washed three times with saturated sodium bicarbonate, then three times with saturated common salt washing, rotary evaporation organic solvent obtains an oily liquid, uses
Methylene chloride/methanol (30:1, v/v) mixed liquor crosses column and obtains compound A；
(3) absorption 50ml hydrazine hydrate, weighs 3.5g compound A in 500ml flask, addition 100ml ethyl alcohol, anti-at 70 DEG C
It answers 3 days, rotary evaporation concentration is extracted with dichloromethane, and dichloromethane extract is washed with water three times, then washes three with saturated common salt
Secondary, organic phase is dry with anhydrous sodium sulfate, and rotary evaporation organic solvent obtains oily compound B；
(4) 1.4g compound B, 0.5g pyrene formaldehyde is weighed in 100ml flask, and 18ml tetrahydrofuran and 32ml second is added
Alcohol reacts 36 hours at 90 DEG C, and ether precipitating is added, and centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, from
The heart obtains colloidal cpd G in triplicate；
(5) preparation of fluorescence vesica: weighing 41.75mg G compound and be dissolved in 5ml water, and obtaining concentration is 1 × 10-
The G compound water solution of 2mol/L is therefrom drawn 30 μ L and is instilled in the water of 3ml, and standing a few minutes can be prepared by fluorescence vesica, make
Imaging of the vesica obtained under transmission electron microscope is as shown in Figure 1.
Embodiment 2:
(1) 50g triethylene glycol monomethyl ether, 100g paratoluensulfonyl chloride and 550ml methylene chloride are mixed and is made it dissolve, so
It is in atropurpureus that sodium hydroxide solution is added dropwise under ice bath stirring afterwards and is examined to solution with pH test paper, stirs 10h under room temperature, is washed with water
Filter, lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, and diluted sodium hydroxide solution is added and stirs
10h, liquid separation are mixed, water layer is washed 1 time with methylene chloride, is then combined with organic phase, is washed with water 2 times, then wash 1 with saturated sodium chloride solution
Secondary, dry with anhydrous sodium sulfate, liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-TEG-Ts；
(2) anhydrous N, N- bis- is added in 50gMe-TEG-Ts, 7.5g gallicin, 5g potassium iodide and 55g potassium carbonate
It in methylformamide, reacts 50 hours at 70 DEG C, rotary evaporation of solvent, is washed solid 1 time with methylene chloride, cleaning solution is used full
It washes 2 times with sodium bicarbonate solution, then is washed 2 times with saturated common salt, rotary evaporation organic solvent obtains an oily liquid, uses volume ratio
The methylene chloride/methanol mixed liquor of 30:1 crosses column and obtains compound A；
(3) it is reacted 2.5 days at 60 DEG C after mixing 40ml hydrazine hydrate, 3g compound A and 90ml ethyl alcohol, rotary evaporation is dense
It is extracted with dichloromethane after contracting, dichloromethane extract is washed with water 2 times, then is washed 2 times with saturated common salt, the anhydrous sulphur of organic phase
Sour sodium is dry, and rotary evaporation of solvent obtains oily compound B；
(4) 30 are reacted at 80 DEG C after mixing 1g compound B, 0.1g pyrene formaldehyde, 15ml tetrahydrofuran and 30ml ethyl alcohol
Hour, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, and centrifugation is repeated 2 times to change
Close object G；
(5) 35mg compound G is dissolved in 3ml water, obtains compound G aqueous solution, drawn 20 μ l compound G aqueous solutions and instill
In 2ml water, fluorescence vesica is obtained after standing 1 minute.
Embodiment 3:
(1) 70g triethylene glycol monomethyl ether, 120g paratoluensulfonyl chloride and 650ml methylene chloride are mixed and is made it dissolve, so
It is in atropurpureus that sodium hydroxide solution is added dropwise under ice bath stirring afterwards and is examined to solution with pH test paper, stirs 15h under room temperature, is washed with water
Filter, lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, and diluted sodium hydroxide solution is added and stirs
15h, liquid separation are mixed, water layer is washed 3 times with methylene chloride, is then combined with organic phase, is washed with water 4 times, then wash 3 with saturated sodium chloride solution
Secondary, dry with anhydrous sodium sulfate, liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-TEG-Ts；
(2) anhydrous N, N- bis- is added in 60gMe-TEG-Ts, 8.5g gallicin, 6g potassium iodide and 65g potassium carbonate
It in methylformamide, reacts 70 hours at 90 DEG C, rotary evaporation of solvent, is washed solid 3 times with methylene chloride, cleaning solution is used full
It washes 4 times with sodium bicarbonate solution, then is washed 4 times with saturated common salt, rotary evaporation organic solvent obtains an oily liquid, uses volume ratio
The methylene chloride/methanol mixed liquor of 30:1 crosses column and obtains compound A；
(3) it is reacted 3.5 days at 80 DEG C after mixing 60ml hydrazine hydrate, 4g compound A and 110ml ethyl alcohol, rotary evaporation
It is extracted with dichloromethane after concentration, dichloromethane extract is washed with water 4 times, then is washed 4 times with saturated common salt, and organic phase is with anhydrous
Sodium sulphate is dry, and rotary evaporation of solvent obtains oily compound B；
(4) reaction 40 is small at 100 DEG C after mixing 2g compound B, 1g pyrene formaldehyde, 25ml tetrahydrofuran and 35ml ethyl alcohol
When, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, and centrifugation is repeated 4 times to obtain chemical combination
Object G；
(5) 45mg compound G is dissolved in 7ml water, obtains compound G aqueous solution, drawn 40 μ l compound G aqueous solutions and instill
In 4ml water, stands and obtain fluorescence vesica after ten minutes.
Claims (8)
1. a kind of fluorescence vesica, which is characterized in that its chemical structural formula is as follows:
2. a kind of preparation method of fluorescence vesica according to claim 1, which comprises the steps of:
(1) using triethylene glycol monomethyl ether, paratoluensulfonyl chloride and methylene chloride as raw material, raw material is mixed and is made it dissolve, then
It is in atropurpureus that sodium hydroxide solution is added dropwise under ice bath stirring and is examined to solution with pH test paper, is stirred to react under room temperature, then uses water
Filter wash, lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, and diluted sodium hydroxide solution is added
It is stirred to react, liquid separation, water layer is washed with methylene chloride, is then combined with organic phase, is washed with water, then washed with saturated sodium chloride solution, is used
Anhydrous sodium sulfate is dry, and liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-TEG-Ts；
It (2), will using Me-TEG-Ts, gallicin, potassium iodide, potassium carbonate and anhydrous n,N-Dimethylformamide as raw material
It is reacted 50-70 hours at 70-90 DEG C after raw material mixing, rotary evaporation of solvent, washs solid with methylene chloride, cleaning solution is used full
It washes with sodium bicarbonate solution, then is washed with saturated common salt, rotary evaporation organic solvent obtains an oily liquid, with the two of volume ratio 30:1
Chloromethanes/methyl alcohol mixed liquor crosses column and obtains compound A；
(3) it using hydrazine hydrate, compound A and ethyl alcohol as raw material, reacts 2.5-3.5 days, rotates at 60-80 DEG C after raw material is mixed
It is extracted with dichloromethane after evaporation and concentration, dichloromethane extract is washed with water, then is washed with saturated common salt, the anhydrous sulphur of organic phase
Sour sodium is dry, and rotary evaporation of solvent obtains oily compound B；
(4) with compound B, pyrene formaldehyde, tetrahydrofuran and ethanol raw material, 30-40 is reacted at 80-100 DEG C after raw material is mixed
Hour, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, and centrifugation repeats to obtain compound
G；
(5) compound G is soluble in water, compound G aqueous solution is obtained, compound G aqueous solution is drawn and instills in water, is obtained after standing glimmering
Light vesica.
3. the preparation method of fluorescence vesica according to claim 2, which is characterized in that specific step is as follows:
(1) mixing 50-70g triethylene glycol monomethyl ether, 100-120g paratoluensulfonyl chloride and 550-650ml methylene chloride makes it
Dissolution, it is in atropurpureus that sodium hydroxide solution is then added dropwise under ice bath stirring and is examined to solution with pH test paper, stirs 10- under room temperature
Filter is washed with water in 15h, and lower layer's organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains glassy yellow grease, dilute hydrogen-oxygen is added
Change sodium solution and stir 10-15h, liquid separation, water layer is washed 1-3 times with methylene chloride, is then combined with organic phase, is washed with water 2-4 times, then use
Saturated sodium chloride solution is washed 1-3 times, dry with anhydrous sodium sulfate, and liquid separation rotary evaporation of solvent obtains glassy yellow grease Me-TEG-
Ts；
(2) nothing is added in 50-60gMe-TEG-Ts, 7.5-8.5g gallicin, 5-6g potassium iodide and 55-65g potassium carbonate
In water n,N-Dimethylformamide, reacted 50-70 hours at 70-90 DEG C, rotary evaporation of solvent washs solid with methylene chloride
1-3 times, cleaning solution is washed 2-4 times with saturated sodium bicarbonate solution, then is washed 2-4 times with saturated common salt, rotary evaporation organic solvent
An oily liquid is obtained, column is crossed with the methylene chloride/methanol mixed liquor of volume ratio 30:1 and obtains compound A；
(3) 2.5-3.5 is reacted at 60-80 DEG C after mixing 40-60ml hydrazine hydrate, 3-4g compound A and 90-110ml ethyl alcohol
It, is extracted with dichloromethane after rotary evaporation concentration, and dichloromethane extract is washed with water 2-4 times, then washes 2-4 with saturated common salt
Secondary, organic phase is dry with anhydrous sodium sulfate, and rotary evaporation of solvent obtains oily compound B；
(4) in 80-100 after 1-2g compound B, 0.1-1g pyrene formaldehyde, 15-25ml tetrahydrofuran and 30-35ml ethyl alcohol being mixed
It is reacted 30-40 hours at DEG C, ether precipitating is added, centrifugation generates precipitating with ether is added after methylene chloride dissolution precipitating, from
The heart repeats 2-4 times to obtain compound G；
(5) 35-45mg compound G is dissolved in 3-7ml water, obtains compound G aqueous solution, draw 20-40 μ l compound G aqueous solution
It instills in 2-4ml water, obtains fluorescence vesica after standing 1-10 minutes.
4. the preparation method of fluorescence vesica according to claim 3, it is characterised in that: be by 60g in the step (1)
Triethylene glycol monomethyl ether, 108g paratoluensulfonyl chloride and the mixing of 600ml methylene chloride.
5. the preparation method of fluorescence vesica according to claim 3, it is characterised in that: in the step (2), be by
Anhydrous N, N- dimethyl formyl is added in 55gMe-TEG-Ts, 7.93g gallicin, 5.59g potassium iodide and 59.8g potassium carbonate
In amine.
6. the preparation method of fluorescence vesica according to claim 3, it is characterised in that: be by 50ml in the step (3)
Hydrazine hydrate, the mixing of 3.5g compound A and 100ml ethyl alcohol.
7. the preparation method of fluorescence vesica according to claim 3, it is characterised in that: be by 1.4g in the step (4)
Compound B, 0.5g pyrene formaldehyde, 18ml tetrahydrofuran and the mixing of 32ml ethyl alcohol.
8. the preparation method of fluorescence vesica according to claim 3, it is characterised in that: in the step (5), be by
41.75mg compound G is dissolved in 5ml water, and obtaining concentration is 1*10-2Then the compound G aqueous solution of mol/L takes 30 μ l compound G
Aqueous solution instills in 3ml water, obtains fluorescence vesica after standing 1-10 minutes.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418947A (en) * | 2015-12-04 | 2016-03-23 | 南开大学 | Fluorescent polymeric vesicle assembled by program control and preparation method thereof |
| CN108558638A (en) * | 2018-03-30 | 2018-09-21 | 中国科学院过程工程研究所 | A kind of preparation method and application of the fluorescence probe based on self-assembly vesicle |
-
2019
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418947A (en) * | 2015-12-04 | 2016-03-23 | 南开大学 | Fluorescent polymeric vesicle assembled by program control and preparation method thereof |
| CN108558638A (en) * | 2018-03-30 | 2018-09-21 | 中国科学院过程工程研究所 | A kind of preparation method and application of the fluorescence probe based on self-assembly vesicle |
Non-Patent Citations (1)
| Title |
|---|
| SUBHAM BHATTACHARJEE ET AL.: "First report of charge-transfer induced heat-set hydrogel. Structural insights and remarkable properties", 《NANOSCALE》 * |
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Application publication date: 20190521 |