CN105115953A - Ratio type nano ball sensor as well as preparation method and application thereof - Google Patents
Ratio type nano ball sensor as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a ratio type nano ball sensor as well as a preparation method and application thereof. The preparation method of the nano ball sensor comprises the following steps: mixing and dissolving a skeleton molecule 9,10-di[4-(2-carbamido-4-[1H]-pyrimidone)benzene]anthracene, a phosphorescence molecule 5,10,15-triphenyl-20-[4-(2-carbamido-4-[1H]-pyrimidone)phenyl]porphyrin palladium and a fluorescent molecule boron fluoride di[4-(2-carbamido-4-[1H]-pyrimidone)benzoyl methane into an organic solution, and injecting the mixture into water containing a surfactant cetyl trimethyl ammonium bromide; carrying out ultrasonic treatment to obtain uniformly-dispersed micro-emulsion; and standing and ageing for one night, and centrifuging to obtain a solid, namely the ratio type nano ball sensor. The nano ball sensor disclosed by the invention has water dissolvability; and the sensor not only has high response on oxygen, but also has the characteristics of easiness for degradation and easiness for regulation and control.
Description
Technical field
The present invention relates to chemical sensor, more specifically, relate to a kind of oxygen sensor and construction method thereof and application, belong to optical sensor technology field.
Background technology
The vital movement of oxygen and biosome is closely related.Clinically have been found that hypoxemia and tumor growth, the diseases such as rheumatic arthritis are closely related.Therefore by detecting distribution and the content situation of oxygen each tissue in human body, the vital movement situation of human body can be understood, for prevention from suffering from the diseases, clinical treatment and new drug development, there is important effect.
And enjoy favor based on the ratio formula oxygen sensor of phosphorescence quenching with the unique advantage of himself, sensor enters in cell, after intracellular Effect of Dissolved Oxygen, can significant change be there is in phosphorescence intensity, by means of laser confocal microscope imaging technique, the Visual retrieval of oxygen content and distribution in cell just can be realized.Some ratio formula optical oxygen sensors are reported in succession in recent years, but still have that some is not enough, and such as, organic molecule water-soluble poor, high molecular polymer is difficult to degraded, and the toxicity of quantum dot etc. all limit their widespread uses in biosome.Therefore present stage needs a kind of oxygen sensor being easy to degrade, bio-compatibility is good of development badly.
Summary of the invention
The present invention's first object is to provide a kind of degraded, oxygen sensor that bio-compatibility is good.
The present invention's second object is to provide a kind of preparation method of oxygen sensor.
The present invention's the 3rd object is to provide a kind of application of oxygen sensor.
For realizing first object, the present invention adopts following technical proposals:
A kind of ratio formula nanosphere sensor, this nanosphere sensor has the structure of formula (I),
Wherein,
There is the phosphorescent molecules 5 of formula (II) structure, 10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium and fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane with formula (IV) structure and there is formula (III) structure molecule of the skeleton 9,10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene by hydrogen bonding for having the ratio formula nanosphere sensor of formula (I) structure.
For realizing second object, the present invention adopts following technical scheme:
A preparation method for ratio formula nanosphere sensor, comprises the following steps:
The molecule of the skeleton 9 of formula (III) structure will be had, 10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene, there is the phosphorescent molecules 5 of formula (II) structure, 10, 15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium is dissolved in chloroform with fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane blended with formula (IV) structure, be injected in the water containing surfactant, ultrasonicly obtain homodisperse microemulsion, leave standstill age overnight, the centrifugal solid that obtains is ratio formula nanosphere sensor.
Preferably, described method comprises the described solid of washing further, particularly, by described solid dispersal in distilled water, then centrifugally obtains solid.Preferably, washing times is three times.
Described surfactant is cetyl trimethyl ammonium bromide or pluronic F-127, and wherein pluronic F-127 belongs to macromolecule non-ionics.
The synthetic method with phosphorescent molecules 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium of formula (II) structure is:
Synthesis has compound 5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin of formula (A) structure;
Synthesis has compound 5,10,15-triphenyl-20-(4-hydroxy phenyl) the porphyrin palladium of formula (B) structure;
Synthesis has compound 5,10,15-triphenyl-20-(4-propargyl alcoholate phenyl) the porphyrin palladium of formula (C) structure;
By compound 5,10, presoma and the styrax diethyl ether of 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium, Quadrupolar hydrogen bond are dissolved in 1, in 2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, logical inert gas eliminates the air in nuclear magnetic tube, with 500W lamp and high pressure mercury 3-5h.Purify through column chromatography after completion of the reaction, obtain 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium with formula (II) structure.
Described inert gas is one or more in nitrogen, argon gas and helium.
The synthesis reference literature (HenkM.Keizer, RintP.Sijbesma, E.W.Meijer.Eur.J.Org.Chem.2004,2553-2555) of the presoma 2-urea groups-4-pyrimidone of Quadrupolar hydrogen bond.
Particularly, there is the compound 5 of formula (A) structure, 10, the synthetic method of 15-triphenyl-20-(4-hydroxy phenyl) porphyrin is: take parahydroxyben-zaldehyde and benzaldehyde, join in propionic acid, when parahydroxyben-zaldehyde and benzaldehyde all dissolve, add the propionic acid solution of pyrroles wherein, leave standstill after back flow reaction and be cooled to room temperature, after in ice bath, add absolute methanol, separate out precipitation, suction filtration, with a large amount of methanol wash filter cake, treat that filter cake is drained, vacuum drying, column chromatography obtains the compound 5 with formula (A) structure, 10, 15-triphenyl-20-(4-hydroxy phenyl) porphyrin.
Particularly, synthesis has the compound 5 of formula (B) structure, 10, the synthetic method of 15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium is: by 5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin is dissolved in N, dinethylformamide, add palladium bichloride, back flow reaction, cold filtration, in filtrate, add large water gaging makes product precipitate, (first should filter) after filtration, wash, 5,10,15-triphenyl-20-(4-hydroxy phenyl) the porphyrin palladium that dry, column chromatography obtains having formula (B) structure.
Particularly, synthesis has the compound 5 of formula (C) structure, 10, the synthetic method of 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium is: by 5, 10, 15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium is dissolved in N, dinethylformamide, add propine bromine and excessive sal tartari, intensification stirring is spent the night, be cooled to room temperature after completion of the reaction, with saturated aqueous common salt and dichloromethane extraction, merge organic phase, use saturated common salt water washing, anhydrous sodium sulfate drying, evaporated under reduced pressure solvent, obtain after column chromatography for separation that there is 5 of formula (C) structure, 10, 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium.
Wherein, the synthetic method of fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane shown in formula (IV) is: by boron fluoride two (4-propenyloxy group) benzoyl methane, presoma and the styrax diethyl ether of Quadrupolar hydrogen bond are dissolved in 1, in 2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, with 500W lamp and high pressure mercury 3-5h.Column chromatography is purified after completion of the reaction, obtains boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane with formula (IV) structure.
The synthesis with molecule of the skeleton 9,10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene of formula (III) structure can with reference to pertinent literature, as Hui-QingPeng, Jiang-FeiXu, Yu-ZheChen.Chem.Commoun.2014,50,1334-1337.
Constructing of ratio formula nanosphere sensor of the present invention is the supermolecule assembled based on Quadrupolar hydrogen bond.
For realizing the 3rd object, the present invention adopts following technical scheme:
Ratio formula nanosphere sensor of the present invention can be used for detecting the dissolved oxygen in cell or tissue.
Beneficial effect of the present invention is as follows:
Nanosphere sensor provided by the present invention is the supermolecule polymer based on Quadrupolar hydrogen bond assembling, it has water-soluble, structural unit used is organic molecule, the Quadrupolar hydrogen bond between molecule is utilized phosphorescent molecules and fluorescence molecule effectively to be assembled, sensor is not only to oxygen high response, and there is the feature of easy degraded, easy-regulating, this oxygen sensor has good using value in bio-imaging.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, the specific embodiment of the present invention is described in further detail.
Fig. 1 illustrates the fluorescence emission spectrum of fluorescence molecule.
Fig. 2 illustrates the phosphorescence emission spectra of phosphorescent molecules in air and nitrogen
Fig. 3 illustrates the scanning electron microscope of ratio formula nanosphere sensor.
Fig. 4 illustrates the transmission electron microscope of ratio formula nanosphere sensor.
Fig. 5 illustrates the dynamic light scattering result figure of ratio formula nanosphere sensor.
Fig. 6 illustrates the ultra-violet absorption spectrum of ratio formula nanosphere sensor.
Fig. 7 illustrates the luminescent spectrum of ratio formula nanosphere sensor.
Fig. 8 illustrates that the ratio of the phosphorescence emission intensity of ratio formula nanosphere sensor and fluorescent emission intensity is to the linear analogue of oxygen concentration, wherein R
n2for the ratio of the phosphorescence emission intensity under condition of nitrogen gas and fluorescent emission intensity, R1 is the ratio of phosphorescence emission intensity under different oxygen concentration and fluorescent emission intensity, R
n2/ R1 is R
n2with the ratio of R1.
Fig. 9 illustrates the phosphor-decay curve of ratio formula nanosphere sensor in air, nitrogen and oxygen atmosphere.
Embodiment
In order to be illustrated more clearly in the present invention, below in conjunction with preferred embodiments and drawings, the present invention is described further.Parts similar in accompanying drawing represent with identical Reference numeral.It will be appreciated by those skilled in the art that specifically described content is illustrative and nonrestrictive, should not limit the scope of the invention with this below.
Embodiment 1
(1) there is the synthesis of phosphorescent molecules 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium of formula (II) structure:
1. be add 250mL propionic acid in the there-necked flask of 1L at capacity, 50 DEG C are warming up to 6 DEG C per minute, 4g parahydroxyben-zaldehyde (32.8mmol) and 10.4g benzaldehyde (98mmol) is added under stirring, after parahydroxyben-zaldehyde and benzaldehyde all dissolve, 9.1mL pyrroles is dissolved in 50mL propionic acid, instill within half an hour in mixed liquor, drip off rear reaction and be warming up to 150 DEG C, continue reaction 1h and obtain black liquor, normal temperature adds 300mL methyl alcohol after leaving standstill and being cooled to room temperature, put into ice bath half an hour, suction filtration obtains purple crystalline precipitate, the a large amount of methyl alcohol of filter cake repeatedly washs, treat that filter cake is drained, evaporated in vacuo obtains purple solid product.Column chromatography obtains compound 5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin with formula (A) structure;
2. by 100mg5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin (0.16mmol) is dissolved in 3.5mLN, dinethylformamide, add 225mg palladium bichloride (1.27mmol), temperature of reaction rises to 150 DEG C of backflow 10min, cold filtration, in filtrate, add large water gaging makes product precipitate, the compound 5 with formula (B) structure is obtained through washing, filtration, drying, column chromatography, 10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium.
3. by 100mg5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium (0.14mmol) is dissolved in 5mLN, dinethylformamide, add 24.78mg propine bromine (0.21mmol) and excessive sal tartari, be warming up to 80 DEG C of stirrings to spend the night, be cooled to room temperature after completion of the reaction, with saturated aqueous common salt and dichloromethane extraction, merge organic phase, saturated common salt is washed, anhydrous sodium sulfate drying, evaporated under reduced pressure solvent, obtains the compound 5 with formula (C) structure after column chromatography for separation, 10,15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium.
4. the presoma 2-urea groups-4-pyrimidone of reference literature (HenkM.Keizer, RintP.Sijbesma, E.W.Meijer.Eur.J.Org.Chem.2004,2553-2555) method synthesis Quadrupolar hydrogen bond;
5. by 206mg compound 5,10,15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium (0.66mmol), the presoma (0.11mmol) of 81mg Quadrupolar hydrogen bond and styrax diethyl ether are dissolved in 1,2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, and logical nitrogen 30min eliminates the air in nuclear magnetic tube, with 500W lamp and high pressure mercury 5h.Purify through column chromatography after completion of the reaction, obtain compound 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium with formula (II) structure.
(2) there is the synthesis of fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane compounds of formula (IV) structure:
By compound 100mg boron fluoride two (4-propenyloxy group) benzoyl methane compounds (0.243mmol), presoma (0.971mmol) and the 20mg styrax diethyl ether (0.07mmol) of 302mg Quadrupolar hydrogen bond are dissolved in 1, in 2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, with 500W lamp and high pressure mercury 5h.Column chromatography is purified after completion of the reaction, obtains boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] benzoyl methane compounds.
(3) there is the synthesis of 9,10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene of formula (III) structure:
Reference literature method synthesis molecule of the skeleton 9,10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene (Hui-QingPeng, Jiang-FeiXu, Yu-ZheChen.Chem.Commoun.2014,50,1334-1337).
The compound 5 of the present invention's synthesis, fluorescence and phosphorescence emission spectrum is as illustrated in fig. 1 and 2 in chloroformic solution for 10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium and boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] benzoyl methane compounds.Test result shows that compound 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium presents red phosphorescent under a nitrogen atmosphere, and under the state of aerobic, phosphorescence intensity is then by quencher; And boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] benzoyl methane compounds blue light-emitting, its luminous intensity does not affect by oxygen.
(4) preparation of ratio formula nanosphere sensor:
By 4.5mg molecule of the skeleton 9,10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene, 0.216mg phosphorescent molecules 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium and 0.094mg fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] benzoyl methane compounds are that the ratio of 20:0.5:0.3 is dissolved in chloroformic solution with mass ratio, be injected in the water (10mL) of 3.8mg trimethylammonium bromide, ultrasonic 25min obtains homodisperse microemulsion.Leave standstill after age overnight, centrifugal 45min obtains solid, and gained solid to be re-dispersed in distilled water and again centrifugal to wash this solid, repeatedly obtains ratio formula nanosphere sensor after three times, pattern as Fig. 3, shown in 4 and 5.
(5) ratio formula nanosphere sensor is to the research of oxygen sensor performance
Prepare the nanosphere sensor aqueous solution 2mL of 32.7 μMs, detect its ultra-violet absorption spectrum, as shown in Figure 6.Oxygen sensor is excited by same excitation wavelength, the corresponding ratio formula emission spectrum under different oxygen concentration atmosphere as shown in Figure 7, can find out that the fluorescence intensity as interior target fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] benzoyl methane does not affect by oxygen concentration, and phosphorescent molecules 5,10, porphyrin palladium is then along with the increase of oxygen concentration for 15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl], and its luminous intensity is constantly by quencher.The ratio of the phosphorescence emission intensity and fluorescent emission intensity that are illustrated in figure 8 ratio formula nanosphere sensor, to the linear analogue of oxygen concentration, shows that this nanosphere sensor is very high to the detection sensitivity of oxygen.Be illustrated in figure 9 the phosphor-decay curve of ratio formula nanosphere sensor in air, nitrogen and oxygen atmosphere, it is good that its notable difference further illustrates the response performance of this nanosphere sensor to oxygen.
Obviously; the above embodiment of the present invention is only for example of the present invention is clearly described; and be not the restriction to embodiments of the present invention; for those of ordinary skill in the field; can also make other changes in different forms on the basis of the above description; here cannot give exhaustive to all embodiments, every belong to technical scheme of the present invention the apparent change of extending out or variation be still in the row of protection scope of the present invention.
Claims (10)
1. a ratio formula nanosphere sensor, is characterized in that, this nanosphere sensor has the structure of formula (I),
Wherein,
2. the preparation method of a ratio formula nanosphere sensor as claimed in claim 1, it is characterized in that, comprise the following steps: the molecule of the skeleton 9 will with formula (III) structure, 10-bis-[4-(2-urea groups-4 [1H]-pyrimidone) benzene] anthracene, there is the phosphorescent molecules 5 of formula (II) structure, 10, 15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] porphyrin palladium is dissolved in chloroformic solution with fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane blended with formula (IV) structure, be injected in the water containing surfactant, ultrasonicly obtain homodisperse microemulsion, leave standstill age overnight, the centrifugal solid that obtains is ratio formula nanosphere sensor.
3. preparation method according to claim 2, is characterized in that, method of stating comprises the described solid of washing further, and described washing step comprises: by described solid dispersal in distilled water, then centrifugally obtains solid; Preferably, washing times is three times.
4. preparation method according to claim 2, is characterized in that, described surfactant is cetyl trimethyl ammonium bromide or pluronic F-127.
5. preparation method according to claim 2, is characterized in that, the synthetic method with phosphorescent molecules 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium of formula (II) structure is:
Synthesis has compound 5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin of formula (A) structure;
Synthesis has compound 5,10,15-triphenyl-20-(4-hydroxy phenyl) the porphyrin palladium of formula (B) structure;
Synthesis has compound 5,10,15-triphenyl-20-(4-propargyl alcoholate phenyl) the porphyrin palladium of formula (C) structure;
By compound 5,10, presoma and the styrax diethyl ether of 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium, Quadrupolar hydrogen bond are dissolved in 1, in 2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, logical nitrogen or argon gas eliminate the air in nuclear magnetic tube, with 500W lamp and high pressure mercury 3-5h; Purify through column chromatography after completion of the reaction, obtain 5,10,15-triphenyl-20-[4-(2-urea groups-4 [1H]-pyrimidone) phenyl] the porphyrin palladium with formula (II) structure
6. preparation method according to claim 5, it is characterized in that, there is the compound 5 of formula (A) structure, 10, the synthetic method of 15-triphenyl-20-(4-hydroxy phenyl) porphyrin is: take parahydroxyben-zaldehyde and benzaldehyde, add in propionic acid, when parahydroxyben-zaldehyde and benzaldehyde all dissolve, add the propionic acid solution of pyrroles wherein, leave standstill after back flow reaction and be cooled to room temperature, after in ice bath, add absolute methanol, separate out precipitation, suction filtration, with a large amount of methanol wash filter cake, treat that filter cake is drained, vacuum drying, column chromatography obtains the compound 5 with formula (A) structure, 10, 15-triphenyl-20-(4-hydroxy phenyl) porphyrin.
7. preparation method according to claim 5, it is characterized in that, there is the compound 5 of formula (B) structure, 10, the synthetic method of 15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium is: by 5,10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin is dissolved in DMF, adds palladium bichloride, back flow reaction, cold filtration, adds large water gaging and product is precipitated in filtrate, obtains having 5 of formula (B) structure through washing, filtration, drying, column chromatography, 10,15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium.
8. preparation method according to claim 5, it is characterized in that, there is the compound 5 of formula (C) structure, 10, the synthetic method of 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium is: by 5, 10, 15-triphenyl-20-(4-hydroxy phenyl) porphyrin palladium is dissolved in N, dinethylformamide, add propine bromine and excessive sal tartari, intensification stirring is spent the night, be cooled to room temperature after completion of the reaction, with saturated aqueous common salt and dichloromethane extraction, merge organic phase, saturated common salt is washed, anhydrous sodium sulfate drying, evaporated under reduced pressure solvent, obtain after column chromatography for separation that there is 5 of formula (C) structure, 10, 15-triphenyl-20-(4-propargyl alcoholate phenyl) porphyrin palladium.
9. preparation method according to claim 2, it is characterized in that, the synthetic method with fluorescence molecule boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane of formula (IV) structure is: by boron fluoride two (4-propenyloxy group) benzoyl methane, presoma and the styrax diethyl ether of Quadrupolar hydrogen bond are dissolved in 1, in 2-ethylene dichloride, mixed solution is placed in nuclear magnetic tube, with 500W lamp and high pressure mercury 3-5h, column chromatography is purified after completion of the reaction, obtain boron fluoride two [4-(2-urea groups-4 [1H]-pyrimidone)] the benzoyl methane with formula (IV) structure.
10. a purposes for nanosphere sensor according to claim 1, is characterized in that, this nanosphere sensor is for detecting the dissolved oxygen in cell or tissue.
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| CN112391047A (en) * | 2019-08-14 | 2021-02-23 | 湖南科技大学 | Temperature stimulation responsive perylene diimide supramolecular fluorescent gel, preparation method and application |
| CN112391047B (en) * | 2019-08-14 | 2023-02-21 | 湖南科技大学 | Temperature stimulation responsive perylene diimide supramolecular fluorescent gel, preparation method and application |
| US11873306B1 (en) | 2023-07-20 | 2024-01-16 | King Faisal University | Nano-sized 5,10,15,20-tetrakis (4-hydroxyphenyl)-porphyrins pd(II) complex for super medicinal applications |
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