CN115028853B - Construction method of phycocyanin-metal organic framework - Google Patents
Construction method of phycocyanin-metal organic framework Download PDFInfo
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- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 20
- 238000010276 construction Methods 0.000 title description 6
- 108010053210 Phycocyanin Proteins 0.000 claims abstract description 39
- 239000013078 crystal Substances 0.000 claims abstract description 16
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 14
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000013110 organic ligand Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000011259 mixed solution Substances 0.000 claims description 30
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 20
- 238000005406 washing Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 229920000128 polypyrrole Polymers 0.000 claims description 10
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 238000005119 centrifugation Methods 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 5
- 239000012498 ultrapure water Substances 0.000 claims description 5
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004729 solvothermal method Methods 0.000 abstract 1
- HHDUMDVQUCBCEY-UHFFFAOYSA-N 4-[10,15,20-tris(4-carboxyphenyl)-21,23-dihydroporphyrin-5-yl]benzoic acid Chemical compound OC(=O)c1ccc(cc1)-c1c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc([nH]2)c(-c2ccc(cc2)C(O)=O)c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc1[nH]2 HHDUMDVQUCBCEY-UHFFFAOYSA-N 0.000 description 14
- 239000011701 zinc Substances 0.000 description 11
- 239000003446 ligand Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 102000034287 fluorescent proteins Human genes 0.000 description 2
- 108091006047 fluorescent proteins Proteins 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000002064 nanoplatelet Substances 0.000 description 1
- 239000002135 nanosheet Substances 0.000 description 1
- 238000003333 near-infrared imaging Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Abstract
The invention discloses a method for constructing an phycocyanin-metal organic framework, which is characterized in that phycocyanin and tetracarboxyl porphyrin are used as organic ligands, zinc nitrate hexahydrate is used as a metal center, and a solvothermal method is adopted to construct a typical phycocyanin-metal organic framework compound. The MOFs material is of a lamellar structure, the fluorescent color is reddish, the crystal purity is high, the service life of the crystal is longer, and the MOFs material has potential application value in the aspect of fluorescence sensing.
Description
Technical Field
The invention relates to a construction method of phycocyanin-metal organic frameworks, which adopts natural fluorescent protein as an organic ligand and a metal center to obtain the fluorescent metal organic frameworks through coordination assembly, and has important significance for constructing the metal organic frameworks with fluorescent characteristics by the natural fluorescent protein.
Background
Fluorescent metal organic frameworks (LMOFs) are an important member of fluorescent molecules, have a designable host-guest structure, porosity, luminescence, host-guest responsiveness and the like, are particularly suitable for being used as carriers of functional materials such as light, electricity, magnetism and the like, and have obtained attractive research results in luminescence regulation, physical and chemical sensing, biological sensing and imaging and have further developed in device application.
Along with the appearance of new construction ligands, modification methods, polymerization methods and loading methods, new functions and new applications of LMOFs are rapidly increased, for example, medical applications such as living body imaging, fluorescence detection and the like which are rapidly developed in recent years can be brought into clinical application only by providing requirements of high quantum yield, long fluorescence lifetime, near infrared imaging and the like for the LMOFs, but also by having expected functions such as biocompatibility, innocuity, stability, diagnosis and treatment integration and the like. And in addition, as photosynthesis based on LMOFs simulated sunlight appears in recent years, plant growth is promoted, which clearly puts requirements on high quantum yield, no toxicity and the like on building units and metal clusters of the LMOFs. In addition, most of the LMOFs in the big punch pins of the light-emitting device are constructed based on lanthanide series, transition metal and synthetic organic fluorescent ligand, and no LMOFs constructed by natural organic fluorescent ligand exists, and although the lanthanide series metal has the advantages of adjustable light color, high luminous intensity and the like, a new path for constructing a new LMOFs light-operated platform is still required to be searched for due to toxicity and non-renewable resources. Thus, for example, a Bio-fluorescent metal-organic framework (Bio-LMOFs) can be constructed by using easily available natural fluorescent molecules as organic ligands, and a biocompatible, stable, high quantum yield and nontoxic light-operated platform can be obtained, which is immeasurable for technological and social development.
Phycocyanin (PC) is a natural bioactive substance which is rare in nature, has both a medicinal curative effect and an outstanding fluorescence effect, has nontoxic and harmless properties and a plurality of medicinal properties, and is often used in the aspects of food health care and the like. In addition, the phycocyanin has a structure similar to that of porphyrin derivatives, and if the phycocyanin is used for fluorescent metal-organic framework materials, the phycocyanin is expected to replace porphyrin or synergistic porphyrin to play an important role in aspects such as fluorescence imaging, medicine carrying, fluorescent probes, electronic components and the like.
Disclosure of Invention
The invention aims to provide a construction method of an phycocyanin-metal organic framework, and the obtained phycocyanin-metal organic framework has strong red fluorescence.
The invention provides a method for constructing an phycocyanin-metal organic framework, which comprises the following steps:
1) Dissolving phycocyanin in ultrapure water until the phycocyanin is uniform and transparent, adding a mixed solution of dimethylformamide and absolute ethyl alcohol, and then adding tetracarboxy porphyrin to prepare a uniform mixed solution with the concentration of an organic ligand of 1.25 mmol/L; wherein, the volume ratio of the dimethylformamide to the absolute ethyl alcohol is 3:1, the molar ratio of the tetracarboxy porphyrin to the phycocyanin is 1:0.5-2;
2) Dissolving zinc nitrate hexahydrate, pyrazine and polypyrrole in a mixed solution of dimethylformamide and absolute ethyl alcohol to prepare a uniform mixed solution with the concentration of zinc nitrate of 1.25 mmol/L; wherein, the mol ratio of zinc nitrate hexahydrate to pyrazine to polypyrrole is 50:20:1, and the volume ratio of dimethylformamide to absolute ethyl alcohol is 3:1, a step of;
3) And then mixing the mixed solution 1 obtained in the step 1) with the mixed solution obtained in the step 2) according to the volume ratio of 1:3, after mixing, ultrasonic dispersing, sealing the reaction system, placing the reaction system in a blast drying oven for reaction at 80 ℃ for 16 hours, taking out the crystal obtained by centrifugation, washing with ethanol, pouring the washed crystal into a surface dish, and drying in vacuum at 50 ℃ for 24 hours to obtain the product.
In step 3), the ultrasonic dispersion is carried out for 10min at the frequency of 40KHz at room temperature.
In step 3), the washing is performed three times with ethanol, each time for not less than 6 hours.
According to the process conditions, the obtained phycocyanin-metal organic frame shows red fluorescence; has a definite crystal structure and microscopic morphology.
The invention has the beneficial effects that: the phycocyanin and the tetracarboxyl porphyrin are used as double ligands to successfully construct the phycocyanin-metal organic frameworks, so that the problem of difficult construction of ordered porous structures Bio-FLMOFs by pure natural molecules is solved.
Drawings
Fig. 1 is an XRD spectrum of examples 1, 2, 3 of the present invention.
Fig. 2 is an SEM microtopography of example 1 of the present invention.
Fig. 3 is an SEM microtopography of example 2 of the present invention.
Fig. 4 is an SEM microtopography of example 3 of the present invention.
Detailed Description
The following examples are further illustrative of the invention and are not intended to limit the scope of the invention.
Example 1:
1) Dissolving phycocyanin in ultrapure water until the phycocyanin is uniform and transparent, adding a mixed solution of dimethylformamide and absolute ethyl alcohol, and then adding tetracarboxy porphyrin to prepare a uniform mixed solution with the concentration of an organic ligand of 1.25 mmol/L; wherein, the volume ratio of the dimethylformamide to the absolute ethyl alcohol is 3:1, the molar ratio of the tetracarboxy porphyrin to the phycocyanin is 1:0.5;
2) Dissolving zinc nitrate hexahydrate, pyrazine and polypyrrole in a mixed solution of dimethylformamide and absolute ethyl alcohol to prepare a uniform mixed solution with the concentration of zinc nitrate of 1.25 mmol/L; wherein, the mol ratio of zinc nitrate hexahydrate to pyrazine to polypyrrole is 50:20:1, and the volume ratio of dimethylformamide to absolute ethyl alcohol is 3:1, a step of;
3) And then mixing the mixed solution 1 obtained in the step 1) with the mixed solution obtained in the step 2) according to the volume ratio of 1:3, after mixing, ultrasonic dispersing, 10min, frequency 40KHz, room temperature, sealing the reaction system, placing in a blast drying oven, reacting for 16h at 80 ℃, taking out the crystal obtained by centrifugation, washing with ethanol three times, washing for 7h each time, pouring the crystal obtained by washing into a surface dish, and drying in vacuum at 50 ℃ for 24h to obtain the product. The obtained powder was designated Zn 2 [(TCPP) 1 (PC) 1 ]。
Example 2:
1) Dissolving phycocyanin in ultrapure water until the phycocyanin is uniform and transparent, adding a mixed solution of dimethylformamide and absolute ethyl alcohol, and then adding tetracarboxy porphyrin to prepare a uniform mixed solution with the concentration of an organic ligand of 1.25 mmol/L; wherein, the volume ratio of the dimethylformamide to the absolute ethyl alcohol is 3:1, the molar ratio of the tetracarboxy porphyrin to the phycocyanin is 1:1;
2) Dissolving zinc nitrate hexahydrate, pyrazine and polypyrrole in a mixed solution of dimethylformamide and absolute ethyl alcohol to prepare a uniform mixed solution with the concentration of zinc nitrate of 1.25 mmol/L; wherein, the mol ratio of zinc nitrate hexahydrate to pyrazine to polypyrrole is 50:20:1, and the volume ratio of dimethylformamide to absolute ethyl alcohol is 3:1, a step of;
3) And then mixing the mixed solution 1 obtained in the step 1) with the mixed solution obtained in the step 2) according to the volume ratio of 1:3, after mixing, ultrasonic dispersing for 10min, the frequency is 40KHz, at room temperature, sealing the reaction system and placing in a blast drying oven for reaction at 80 ℃ for 16h,taking out the crystal obtained by centrifugation, washing with ethanol for three times, washing for 7 hours each time, pouring the crystal obtained by washing into a surface dish, and drying in vacuum at 50 ℃ for 24 hours to obtain the crystal. The obtained powder was designated Zn 2 [(TCPP) 1 (PC) 2 ]。
Example 3:
1) Dissolving phycocyanin in ultrapure water until the phycocyanin is uniform and transparent, adding a mixed solution of dimethylformamide and absolute ethyl alcohol, and then adding tetracarboxy porphyrin to prepare a uniform mixed solution with the concentration of an organic ligand of 1.25 mmol/L; wherein, the volume ratio of the dimethylformamide to the absolute ethyl alcohol is 3:1, the molar ratio of the tetracarboxy porphyrin to the phycocyanin is 1:2;
2) Dissolving zinc nitrate hexahydrate, pyrazine and polypyrrole in a mixed solution of dimethylformamide and absolute ethyl alcohol to prepare a uniform mixed solution with the concentration of zinc nitrate of 1.25 mmol/L; wherein, the mol ratio of zinc nitrate hexahydrate to pyrazine to polypyrrole is 50:20:1, and the volume ratio of dimethylformamide to absolute ethyl alcohol is 3:1, a step of;
3) And then mixing the mixed solution 1 obtained in the step 1) with the mixed solution obtained in the step 2) according to the volume ratio of 1:3, after mixing, performing ultrasonic dispersion for 10min, the frequency is 40KHz, at room temperature, sealing the reaction system, placing the reaction system in a blast drying oven for reaction at 80 ℃ for 16h, taking out the crystal obtained by centrifugation, washing with ethanol three times, washing for 7h each time, pouring the crystal obtained by washing into a surface dish, and performing vacuum drying at 50 ℃ for 24h to obtain the crystal. The obtained powder was designated Zn 2 [(TCPP) 2 (PC) 1 ]。
XRD patterns of examples 1, 2, and 3 are shown in fig. 1.
XRD for Zn 2 [(TCPP) x (PC) y ]The structure is characterized, XRD spectrum shows that four main characteristic peaks are respectively positioned at 7.6 degrees, 17.6 degrees, 21.3 degrees and 22.7 degrees of the synthesized sample, and the synthesized sample shows Zn 2 [(TCPP) x (PC) y ]Having a defined crystal structure, but Zn 2 [(TCPP) 1 (PC) 1 ]The regularity is further improved.
SEM topography for examples 1, 2, and 3 are shown in fig. 2, 3, and 4, respectively.
(a) Zn 2 [(TCPP) 1 (PC) 1 ] (×10k); (b) Zn 2 [(TCPP) 1 (PC) 2 ] (×10k); (c) Zn 2 [(TCPP) 2 (PC) 1 ] (×10k)。
From Zn 2 [(TCPP) x (PC) y ]As can be seen from the SEM morphology of (2), fig. 2 forms a curly fold structure, which can be attributed to the fact that there is still some interaction between the organic ligands TCPP and PC when they coordinate with zinc ions, resulting in the surface deformation of the nanoplatelets, but Zn 2 [(TCPP) 1 (PC) 1 ]The shape regularity is poor. When the PC content was increased, i.e., FIG. 3, zn was found 2 [(TCPP) 1 (PC) 2 ]The curling wrinkles still exist, but the individual areas form ordered tetragonal blocky sheets, which are similar to the overall morphology of Zn-PC, probably because the phycocyanin concentration is high in the proportion, and the phycocyanin grows and extends in the vertical direction preferentially, and the ordered structure also shows that the phycocyanin has the potential of building MOFs. However, when the TCPP content is large, i.e. fig. 4, it is obvious that the wrinkles disappear, the nano sheets are closely arranged, ordered, and have high orientation, and the oriented channels are easier to form.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications and substitutions may be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims.
Claims (3)
1. A method for constructing an phycocyanin-metal organic framework, comprising the steps of:
1) Dissolving phycocyanin in ultrapure water until the phycocyanin is uniform and transparent, adding a mixed solution of dimethylformamide and absolute ethyl alcohol, and then adding tetracarboxy porphyrin to prepare a uniform mixed solution with the concentration of an organic ligand of 1.25 mmol/L; wherein, the volume ratio of the dimethylformamide to the absolute ethyl alcohol is 3:1, the molar ratio of the tetracarboxy porphyrin to the phycocyanin is 1:0.5-2;
2) Dissolving zinc nitrate hexahydrate, pyrazine and polypyrrole in a mixed solution of dimethylformamide and absolute ethyl alcohol to prepare a uniform mixed solution with the concentration of zinc nitrate of 1.25 mmol/L; wherein, the mol ratio of zinc nitrate hexahydrate to pyrazine to polypyrrole is 50:20:1, and the volume ratio of dimethylformamide to absolute ethyl alcohol is 3:1, a step of;
3) And then mixing the mixed solution 1 obtained in the step 1) with the mixed solution obtained in the step 2) according to the volume ratio of 1:3, after mixing, ultrasonic dispersing, sealing the reaction system, placing the reaction system in a blast drying oven for reaction at 80 ℃ for 16 hours, taking out the crystal obtained by centrifugation, washing with ethanol, pouring the washed crystal into a surface dish, and drying in vacuum at 50 ℃ for 24 hours to obtain the product.
2. The method of constructing an phycocyanin-metal organic framework according to claim 1, wherein in step 3), the ultrasonic dispersion is performed for 10min at a frequency of 40KHz at room temperature.
3. The method of constructing an phycocyanin-metal organic framework according to claim 1, wherein in step 3), the washing is performed three times with ethanol, each time for not less than 6 hours.
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|---|---|---|---|---|
| CN103003368A (en) * | 2010-03-17 | 2013-03-27 | 纳诺洛吉卡股份公司 | Enhanced folic acid fluorescent material, multifluorescent porous compositions of matter and potential applications thereof |
| CN106749348A (en) * | 2016-11-22 | 2017-05-31 | 南开大学 | A kind of metal-organic framework material and preparation method and application |
| CN110801520A (en) * | 2019-09-25 | 2020-02-18 | 广东石油化工学院 | Preparation method of spirulina bioluminescence metal organic framework compound |
| CN111004623A (en) * | 2019-12-20 | 2020-04-14 | 河北科技大学 | Porphyrin fluorescent material and preparation method thereof |
| CN114748644A (en) * | 2022-05-20 | 2022-07-15 | 齐齐哈尔大学 | Preparation method of phycocyanin molecularly imprinted drug carrier with ZIF-8 as matrix |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103003368A (en) * | 2010-03-17 | 2013-03-27 | 纳诺洛吉卡股份公司 | Enhanced folic acid fluorescent material, multifluorescent porous compositions of matter and potential applications thereof |
| CN106749348A (en) * | 2016-11-22 | 2017-05-31 | 南开大学 | A kind of metal-organic framework material and preparation method and application |
| CN110801520A (en) * | 2019-09-25 | 2020-02-18 | 广东石油化工学院 | Preparation method of spirulina bioluminescence metal organic framework compound |
| CN111004623A (en) * | 2019-12-20 | 2020-04-14 | 河北科技大学 | Porphyrin fluorescent material and preparation method thereof |
| CN114748644A (en) * | 2022-05-20 | 2022-07-15 | 齐齐哈尔大学 | Preparation method of phycocyanin molecularly imprinted drug carrier with ZIF-8 as matrix |
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