CN113930234B - Nanometer material and preparation method and application thereof - Google Patents
Nanometer material and preparation method and application thereof Download PDFInfo
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- CN113930234B CN113930234B CN202111250012.6A CN202111250012A CN113930234B CN 113930234 B CN113930234 B CN 113930234B CN 202111250012 A CN202111250012 A CN 202111250012A CN 113930234 B CN113930234 B CN 113930234B
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- 239000000463 material Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000002086 nanomaterial Substances 0.000 claims abstract description 47
- 239000008346 aqueous phase Substances 0.000 claims abstract description 21
- 230000003111 delayed effect Effects 0.000 claims abstract description 17
- 239000004094 surface-active agent Substances 0.000 claims abstract description 13
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 70
- 229960003638 dopamine Drugs 0.000 claims description 35
- 238000004020 luminiscence type Methods 0.000 claims description 26
- 238000001514 detection method Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 238000007725 thermal activation Methods 0.000 claims description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000004793 Polystyrene Substances 0.000 claims description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 5
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- 150000001875 compounds Chemical class 0.000 claims description 3
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- 238000001226 reprecipitation Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002105 nanoparticle Substances 0.000 abstract description 39
- 238000001378 electrochemiluminescence detection Methods 0.000 description 46
- 239000002904 solvent Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 17
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 13
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 239000002096 quantum dot Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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- 235000019154 vitamin C Nutrition 0.000 description 1
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- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- G01N21/76—Chemiluminescence; Bioluminescence
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Abstract
The invention discloses a nano material and a preparation method and application thereof. The nanomaterial includes a core including a thermally activated delayed fluorescence material and a shell including a surfactant. The nano material provided by the invention is a nano particle of a surfactant-coated heat-activated delayed fluorescent material, has excellent electrochemiluminescence intensity and stable anode electrochemiluminescence performance, and has the advantages of simple preparation method steps, low-cost and easily-obtained material and good stability; the nano material can be widely applied to the fields of aqueous phase electrochemiluminescence systems and biosensing.
Description
Technical Field
The invention belongs to the field of materials, and particularly relates to a nano material and a preparation method and application thereof.
Background
The current aqueous electrochemiluminescence (Electrogenerated chemiluminescence, ECL) systems are mainly divided into two types, the first type mainly comprising traditional metal complex systems and other metal complex modified nanosystems; the second type is an inorganic quantum dot or nanomaterial system. The ECL luminescent materials with the two aqueous systems have the advantages of relatively early development and mature technology, but the materials are rich in metal elements, scarce in material sources and metal toxicity, so that the ECL luminescent materials have the defects in cost and environmental protection. In contrast, the organic ECL luminous system based on the carbon-rich structure has the advantages of environmental protection, no toxicity, low price, easy obtainment, adjustable photoelectric property, easy synthesis and functionalization, good biocompatibility and the like, and is valued and developed by people. Organic micromolecules and macromolecule nano-materials with aggregation-induced emission effect are also developed successively, and particularly based on the self-aggregation effect of the organic micromolecules and macromolecule nano-materials in an aqueous phase system, the organic micromolecules and macromolecule nano-materials are successfully applied to the aqueous phase ECL system, and high luminous efficiency is obtained. However, current organic compounds or polymers that do not contain noble metals still face the common problem of insufficient luminous efficiency in aqueous ECL system applications. In particular, the existing aqueous phase pure organic ECL detection system belongs to fluorescence luminescence from the luminescence mechanism, and according to the spin quantum statistical theory, under the condition of electric excitation, the generation ratio of excitons on a singlet state and a triplet state is about 25 percent: 75%, both the annihilation ECL pathway and the coreactant ECL pathway cannot be utilized for triplet excitons generated by recombination on these light-emitting materials, and therefore the upper limit of ECL light-emitting efficiency is only 25%. Therefore, the existing aqueous phase pure organic ECL detection system is limited by common traditional fluorescence physical properties, so that ECL efficiency is low, and development and application prospects are limited.
The existing aqueous ECL material mainly has four defects: 1) The existing aqueous ECL materials are mainly divided into a traditional metal complex system, an inorganic quantum dot or nano material system and an organic system based on a carbon-rich structure, and although ECL luminescent materials of the first two aqueous systems are early and mature in development, the materials are rich in metal elements, scarce in sources and also have metal toxicity, and the defects in cost, environmental protection property and the like exist. 2) According to the existing aqueous organic ECL luminescence mechanism, the annihilation ECL pathway or the coreactant ECL pathway is limited by luminescence physical mechanism, and from the aspect of spin inhibition rule, triplet excitons generated by the luminescent materials in the electro-oxidation reduction process cannot be utilized (accounting for about 75% of the total exciton number), so that only 25% of singlet excitons transit to the ground state to emit light, and ECL luminescence efficiency is low. 3) Because the organic heat-activated delayed fluorescence (Thermally activated delayed fluorescence, abbreviated as TADF) material is insoluble in water and cannot be stably stored in an aqueous phase, the TADF nanoparticle is often required to be coated by a surfactant in the process of preparing the nanoparticle, so that the TADF nanoparticle can stably exist in the microemulsion, and the ECL performance of the material can be directly influenced by the choice of the coating agent. 4) Although Niu Li and the like report that the small molecule TADF luminescent material 4CzIPN realizes the water-phase ECL of a TADF material system under the functionalization of a DEPEG-PEG2000 wrapping agent for the first time, the application of the solid ECL of the TADF material in the biological sensing of the water-phase system is not reported yet, and the solid ECL of the TADF material is still in a blank state at present although the solid ECL has very important practical significance.
The thermally activated delayed fluorescence organic luminescent material is a new generation organic photoelectric material and has been widely applied to the field of organic electroluminescent diodes. The material has very small energy gap between the lowest excited singlet state and the lowest excited triplet state, so that triplet excitons can be enabled to cross back to the singlet state through reverse intersystem crossing through thermal activation of the environment, and further effective utilization of 100% of all excitons is realized. Therefore, from the aspects of ECL foundation and application, development of a novel efficient aqueous-phase organic ECL luminescent system is urgently needed to expand the application range of aqueous-phase ECL and reduce the cost of detection application.
Disclosure of Invention
In order to overcome the problems of the prior art, one of the purposes of the present invention is to provide a nanomaterial; the second object of the present invention is to provide a method for preparing such nanomaterial; it is a further object of the present invention to provide the use of such nanomaterials; the fourth object of the present invention is to provide an aqueous phase electrochemical luminescence sensor; the fifth object of the present invention is to provide a method for detecting dopamine.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the first aspect of the present invention provides a nanomaterial comprising a core and a shell;
the core comprises a thermally activated delayed fluorescence material; the shell layer includes a surfactant.
Preferably, the thermally activated delayed fluorescence material is a conjugated polymer with triazine groups in the side chains.
Preferably, the thermal activation delay fluorescent material is a compound with a structure shown in a formula (I);
in the formula (I), R 1 、R 2 Independently selected from substituted or unsubstituted C2-C8 alkyl groups; r is R 3 、R 4 Independently selected from substituted or unsubstituted C4-C10 alkyl groups; r is R 5 、R 6 Independently selected from substituted or unsubstituted C1-C6 alkyl groups; n is a positive integer of 2 to 250.
Further preferably, the thermally activated delayed fluorescence material is a compound of the structure shown in formula (I); in the formula (I), R 1 、R 2 Independently selected from C4-C8 alkyl groups; r is R 3 、R 4 Independently selected from C6-C10 alkyl; r is R 5 、R 6 Independently selected from C2-C6 alkyl; n is a positive integer of 2 to 200.
Still further preferably, the thermal activation delayed fluorescence has the structural formula:
n is a positive integer of 2 to 200.
Preferably, the surfactant comprises at least one of polystyrene maleic anhydride, polybutene maleic anhydride, polystyrene sulfonic acid, polystyrene acrylic acid; further preferably, the surfactant comprises at least one of polystyrene maleic anhydride and polybutene maleic anhydride; still more preferably, the surfactant is polystyrene maleic anhydride.
Preferably, the structural formula of the polystyrene maleic anhydride is shown as a formula (II):
in the formula (II), a and b are positive integers respectively.
A second aspect of the present invention provides a method for preparing a nanomaterial according to the first aspect of the present invention, comprising the steps of:
and mixing the thermal activation delay fluorescent material with a surfactant for reaction to obtain the nano material.
Preferably, the reaction comprises a reprecipitation process.
Preferably, the reprecipitation method includes the steps of:
and dissolving the thermal activation delay fluorescent material and the surfactant in a good solvent, and then mixing with a poor solvent to obtain the nano material.
Preferably, the mass volume ratio of the thermal activation delay fluorescent material to the good solvent is 1g: (1000-15000) mL; further preferably, the mass-to-volume ratio of the thermal activation delay fluorescent material to the good solvent is 1g: (3000-10000) mL; still further preferably, the mass to volume ratio of the thermally activated delayed fluorescence material to the good solvent is 1g: (5000-8000) mL.
Preferably, the volume ratio of the good solvent to the poor solvent is 1: (3-10); further preferably, the volume ratio of the good solvent to the poor solvent is 1: (4-8); still further preferably, the volume ratio of the good solvent to the poor solvent is 1: (4-6).
Preferably, the good solvent comprises at least one of tetrahydrofuran, ethanol, methanol, acetone, pyridine and piperidine; further preferably, the good solvent comprises at least one of tetrahydrofuran, ethanol, pyridine and piperidine; still more preferably, the good solvent is tetrahydrofuran.
Preferably, the poor solvent is water.
Preferably, the method further comprises a step of drying and removing the good solvent after the good solvent mixed solution is mixed with the poor solvent.
Preferably, the temperature of the drying step is 40-70 ℃; further preferably, the temperature of the drying step is 45 ℃ to 60 ℃.
Preferably, the mixing reaction further comprises a step of filtering.
Preferably, the pore size of the filtration is 0.2 μm to 0.3 μm; further preferably, the pore size of the filtration is 0.2 μm to 0.25 μm.
A third aspect of the invention provides the use of a nanomaterial according to the first aspect of the invention in the field of biosensing.
Preferably, the biosensing field is the field of dopamine detection.
In a fourth aspect the invention provides an aqueous phase electrochemical luminescence sensor comprising a nanomaterial according to the first aspect of the invention.
Preferably, the preparation method of the aqueous phase electrochemical luminescence sensor comprises the following steps:
the nanomaterial of the first aspect of the invention is mixed with an organic solvent and then coated on the surface of an electrode, or the nanomaterial is mixed with water, and then the electrode is placed in an aqueous phase electrolytic cell, so that the aqueous phase electrochemical luminescence sensor is obtained.
Preferably, the electrode is a glassy carbon electrode.
Preferably, the electrode further comprises a polishing treatment step before the nano material is coated.
Preferably, the polishing powder is alumina powder; further preferably, the polishing-treated powder is an alumina powder having a diameter of 0.04 μm to 0.06 μm.
Preferably, the organic solvent comprises a phenolic solvent; further preferably, the organic solvent comprises naphthol.
Preferably, the nanomaterial is an aqueous nanomaterial dispersion; further preferably, the aqueous nanomaterial dispersion has a concentration of 30 μg/mL to 50 μg/mL.
Preferably, the volume ratio of the organic solvent to the aqueous nanomaterial dispersion is 1: (10-30); further preferably, the volume ratio of the organic solvent to the aqueous nanomaterial dispersion is 1: (15-25).
In a fifth aspect, the present invention provides a method for detecting dopamine, comprising the steps of:
the aqueous electrochemical luminescence sensor provided according to the fourth aspect of the present invention is used for detecting a solution containing dopamine.
Preferably, the concentration of the dopamine solution is 10 mu mol/L to 1000 mu mol/L; further preferably, the concentration of the dopamine solution is 50 to 500. Mu. Mol/L.
Preferably, the dopamine-containing solution further contains a reducing agent.
Preferably, the reducing agent comprises at least one of oxalic acid, oxalate, citric acid and vitamin C; further preferably, the reducing agent is an oxalate.
Preferably, the concentration of the reducing agent is 0.02mol/L to 0.06mol/L; further preferably, the concentration of the reducing agent is 0.03mol/L to 0.05mol/L.
Preferably, the dopamine-containing solution further comprises an electrolyte.
Preferably, the electrolyte is phosphate buffer salt solution; further preferably, the phosphate buffer salt solution has a concentration of 0.05mol/L to 0.2mol/L.
Preferably, the scanning potential range of the electrochemical luminescence sensor is 0V-3V; further preferably, the electrochemical luminescence sensor has a scanning potential range of 0V to 1.6V.
Preferably, the scanning speed of the electrochemical luminescence sensor is 0.2V/s-0.3V/s; further preferably, the electrochemical luminescence sensor scans at a rate of 0.24V/s to 0.26V/s.
The beneficial effects of the invention are as follows:
the nano material provided by the invention is a nano particle of a surfactant-coated heat-activated delayed fluorescent material, has excellent electrochemiluminescence intensity and stable anode electrochemiluminescence performance, and has the advantages of simple preparation method steps, low-cost and easily-obtained material and good stability; the nano material can be widely applied to the fields of aqueous phase electrochemiluminescence systems and biosensing.
In particular, the invention has the following advantages:
1. compared with a common organic nanoparticle ECL system, the aqueous phase TADF nanoparticle prepared by the invention can completely utilize an aqueous phase system to test environmental electric excitation conditions without spin inhibition based on a photoelectrochemical mechanism of thermal activation delayed fluorescence, and the generated singlet and triplet excitons are all involved in luminescence, so that ECL luminous efficiency is obviously improved, and theoretically, the ECL efficiency can reach 100 percent, and the luminous efficiency is high. Although the prior metal complex water-soluble ECL luminescent materials (such as metal ruthenium, iridium, platinum complex and the like) have higher ECL efficiency, expensive precious metals are needed to be consumed, the material cost is high and the material has certain toxicity, and the thermal activation delayed fluorescence nanomaterial provided by the invention does not contain heavy metals and rare metals, so that the ECL luminescent material has high ECL efficiency, does not contain any metal element, is low in cost and easy to obtain, has low toxicity and is a TADF organic polymer material with good chemical stability.
2. The preparation method of the nano material provided by the invention has the advantages of simple steps, low-cost and easily obtained materials, good stability and simple and convenient operation.
3. The TADF material is applied to the field of water-phase ECL system biosensing for the first time, particularly has higher sensitivity and wider linear range in the dopamine detection process, the detection range can reach 50 mu mol/L-500 mu mol/L, and the lower limit of detection concentration is 16.67 mu mol/L.
Drawings
FIG. 1 is a schematic illustration of PAPTC nanoparticle preparation.
FIG. 2 is a schematic representation of the basic structure of a prepared "redox" coreactant aqueous ECL device.
Fig. 3 is a schematic diagram of the principle of luminescence of aqueous phase electrochemiluminescence based on thermally activated delayed fluorescent material nanomaterials.
FIG. 4 is a transmission electron microscope image of PAPTC nanoparticles in example 1.
FIG. 5 shows PAPTC nanoparticle/Na of example 1 2 C 2 O 4 A bulk anode electrochemiluminescence graph.
FIG. 6 shows PAPTC nanoparticle/Na of example 1 2 C 2 O 4 And (5) testing the electrochemical luminescence cycling stability of the system.
FIG. 7 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 The detection principle of the dopamine sensor constructed by the anode electrochemiluminescence system is schematically shown.
FIG. 8 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 The electrochemical luminous intensity change patterns of dopamine with different concentrations are added into the system.
FIG. 9 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 Stability test chart of the system with 100. Mu. Mol/L dopamine.
FIG. 10 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 And (3) a linear relation graph of the electrochemical luminous intensity of the system along with the change of the concentration of the dopamine.
FIG. 11 shows the PAPTC nanoparticle/Na of example 1 for three main biomass pairs 2 C 2 O 4 And (5) an anti-interference test chart for detecting dopamine by using electrochemiluminescence of the system.
Detailed Description
Specific implementations of the invention are further described below with reference to the drawings and examples, but the implementation and protection of the invention are not limited thereto. It should be noted that the following processes, if not specifically described in detail, can be realized or understood by those skilled in the art with reference to the prior art. The reagents or instruments used did not identify the manufacturer and were considered conventional products available commercially.
Example 1
(1) Preparation of PAPTC:
poly-3,6-carbazole-9, 9-dihexyl-10- (4, 6-di-tert-butyl-1,3, 5-triazin-2-yl) phenyl) -9,10-dihydroacridine (poly-3, 6-carbazol-9, 9-dihexal-10- (4, 6-di-tert-butyl-1,3, 5-triazin-2-yl) phenyl) -9, 10-dihydroacridine) is abbreviated as PAPTC, and has the structure shown in the specification, wherein n is an integer between 2 and 200, and the specific preparation process is carried out by referring to Macromolecules 2016,49,11,4373-4377;
(2) Preparation of the nanomaterial:
200. Mu.g of PAPTC and 66. Mu.g of polystyrene maleic anhydride reagent (PSMA) were dissolved in 2mL of Tetrahydrofuran (THF) to give a precursor solution. 2mL of precursor liquid is injected into 10mL of water with the assistance of ultrasound; followed by drying at 50 ℃ to remove THF; filtration and sizing using a 0.22 μm filter head gave 40 μg/mL PAPTC nanoparticle dispersion. FIG. 1 is a schematic illustration of PAPTC nanoparticle preparation.
(3) Pretreatment of a glassy carbon electrode:
polishing the glassy carbon electrode with 0.05 mu m alumina powder, ultrasonic cleaning with ultrapure water, ethanol and ultrapure water, and blow-drying the electrode surface with nitrogen.
(4) Preparing a nano material modified glassy carbon electrode:
firstly, 200 mu L of PAPTC nano particles and 10 mu L of naphthol are mixed and ultrasonically treated for 5 minutes, then 20 mu L of PAPTC nano particle dispersed liquid drops are sucked by a liquid-transferring gun and are placed on the surface of a treated glassy carbon electrode, then the glassy carbon electrode is dried under an infrared lamp, and the PAPTC nano particle modified working electrode is obtained after the PAPTC nano particles are dried and formed into a film and is used as a solid-state electrochemical luminescence sensor.
The coating method adopts common coating methods in the field, such as dripping, spin coating, knife coating and the like, can load the thermally activated delayed fluorescent nanomaterial on a working electrode, and can also directly dilute the prepared water-soluble nanoparticle solution into an aqueous ECL test solution according to any optimized proportion for aqueous ECL test.
Performance testing
1. Electrochemiluminescence intensity test of nanomaterial-modified electrochemiluminescence sensor
FIG. 2 is a schematic representation of the basic structure of a prepared "redox" coreactant aqueous ECL device. Taking solid ECL water phase test with water-soluble TADF nanomaterial directly supported on the working electrode as an example, the water-soluble TADF nanomaterial comprises an electrolytic cell 1 and an electrochemical test control power supply 7. A working electrode 2 with a TADF nano material modification layer 8 on the surface, a counter electrode 3, a reference electrode 4, solvent water 5, a supporting electrolyte 6, an oxidation-reduction type coreactant 9 are arranged or contained in the electrolytic cell 1, wherein the supporting electrolyte, the solvent water and the oxidation-reduction type coreactant are mutually dissolved to form an aqueous electrochemical environment. The solvent water, supporting electrolyte, co-reactant, electrochemical test control power source type, driving mode and the like in the ECL structure are not particularly required, various procedures for preparing the aqueous phase ECL and the specific structural layout of ECL constituent elements in FIG. 2 are also not particularly required, and the common operation in the industry is adopted.
Fig. 3 is a schematic diagram of the principle of luminescence of aqueous phase electrochemiluminescence based on thermally activated delayed fluorescent material nanomaterials. FIG. 4 is a transmission electron microscope image of PAPTC nanoparticles in example 1.
First, a specific amount of Na is weighed 2 C 2 O 4 The solid was dissolved in 0.1mol/L PBS (pH 7.45) to give Na 2 C 2 O 4 PBS electrolyte with concentration of 40mmol/L, wherein Na 2 C 2 O 4 As an anode co-reactant for the electrochemical luminescence of the PAPTC nanoparticles, a PBS solution was used as an electrolyte solution. The prepared PAPTC nanoparticle modified glassy carbon electrode is used as a working electrode, an Ag/AgCl electrode is used as a reference electrode, a platinum wire electrode is used as a counter electrode, and the three-electrode system is immersed into 3mL of Na containing 40mmol/L 2 C 2 O 4 Is added to the PBS solution. PAPTC nanoparticle/Na by cyclic voltammetry electrochemical testing 2 C 2 O 4 The electrochemiluminescence intensity of the system, the scanning potential range is 0-1.6V, and the scanning speed is 0.25V/s. FIG. 5 shows PAPTC nanoparticle/Na of example 1 2 C 2 O 4 A body anode electrochemiluminescence graph, wherein a represents a modified electrode and a coreactant 40mm Na 2 C 2 O 4 And the luminous intensity under the PBS condition, wherein b represents the luminous intensity under the condition of the modified electrode and the PBS, and c represents the luminous intensity under the condition of the bare electrode and the PBS. Advancing oneThe stability profile was obtained by a step test, FIG. 6 shows PAPTC nanoparticle/Na of example 1 2 C 2 O 4 And (5) testing the electrochemical luminescence cycling stability of the system. As can be seen from FIG. 6, the PAPTC nanoparticle/Na of example 1 2 C 2 O 4 The system has excellent electrochemiluminescence stability.
2. Testing of the relationship between different dopamine concentrations and electrochemiluminescence intensities
FIG. 7 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 The detection principle of the dopamine sensor constructed by the anode electrochemiluminescence system is schematically shown. Wherein RET (Resonant Energy Transfer) represents resonance energy transfer; GCE (Glassy Carbon Electrode) it represents a glassy carbon electrode.
Configuration of PBS electrolytes containing different concentrations of dopamine: first, a specific amount of Na is weighed 2 C 2 O 4 The solid was dissolved in 0.1mol/L PBS to give Na 2 C 2 O 4 PBS electrolyte with concentration of 40mmol/L, wherein Na 2 C 2 O 4 As co-reactant for the electrochemiluminescence of PAPTC nanoparticles, PBS solution was used as electrolyte solution. Adding different amounts of dopamine solution to obtain Na containing dopamine with different concentrations 2 C 2 O 4 +PBS solution (0. Mu. Mol/L, 1. Mu. Mol/L, 5. Mu. Mol/L, 50. Mu. Mol/L, 100. Mu. Mol/L, 150. Mu. Mol/L, 200. Mu. Mol/L, 300. Mu. Mol/L, 400. Mu. Mol/L, 500. Mu. Mol/L).
Electrochemiluminescence test of dopamine at different concentrations: after stable electrochemiluminescence intensity is obtained, the three-electrode system is immersed into Na with different dopamine concentrations in sequence 2 C 2 O 4 In +PBS solution, PAPTC nanoparticle/Na was continuously tested by cyclic voltammetry electrochemical mode 2 C 2 O 4 The electrochemiluminescence intensity of the system, the scanning potential range is 0-1.6V, and the scanning speed is 0.25V/s. FIG. 8 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 The electrochemical luminous intensity change patterns of dopamine with different concentrations are added into the system. The arrows in the figure indicate the direction of increasing dopamine concentration in sequence (0. Mu. Mol/L, 1. Mu. Mol/L,as can be seen from FIG. 8, the electrochemical luminescence intensity gradually decreases with increasing dopamine concentration, which indicates that the sensor has a wider dopamine detection range, and the detection range can reach 50 mu mol/L-500 mu mol/L. FIG. 9 shows PAPTC nanoparticle/Na in example 1 2 C 2 O 4 Stability test chart of the system with 100. Mu. Mol/L dopamine. The electrolyte containing the dopamine with the concentration of 100 mu mol/L is subjected to a cycle test, the luminous intensity of the electrolyte is basically stable after 10 cycles of scanning, and the Relative Standard Deviation (RSD) is 0.16%, so that the sensor has excellent stability.
And (3) establishing a linear relation: taking the reciprocal of the added dopamine concentration c value as an abscissa, and taking the initial electrochemiluminescence intensity I as an axis 0 With the electrochemiluminescence intensity I and the initial electrochemiluminescence intensity I 0 The ratio of the difference ΔI of (a) is the ordinate to establish a standard linear regression curve, and FIG. 10 is the PAPTC nanoparticle/Na of example 1 2 C 2 O 4 And (3) a linear relation graph of the electrochemical luminous intensity of the system along with the change of the concentration of the dopamine. The linear regression equation is: y=393x+0.4899 (correlation coefficient R 2 =0.997), demonstrating a minimum detection limit of dopamine of up to 16.6 μmol/L.
Interference immunity test: the tamper resistance test is an important performance indicator of a sensor that determines whether the sensor can be used for actual sample detection. The 3 most common life substances were selected for the anti-interference test of the prepared sensor, wherein the concentration of the interfering substances is 500. Mu. Mol/L, the concentration of the dopamine to be detected is 500. Mu. Mol/L, and FIG. 11 shows the PAPTC nanoparticle/Na of example 1 for three main life substances 2 C 2 O 4 And (5) an anti-interference test chart for detecting dopamine by using electrochemiluminescence of the system. Figure 11 shows that other interfering substances have little interference with dopamine detection.
The water-soluble TADF nanomaterial provided by the invention can stably exist in a water phase system and maintain excellent fluorescence stability. According to the invention, polystyrene maleic anhydride is selected as an anionic surfactant to encapsulate TADF nanoparticles so that the TADF nanoparticles have excellent ECL stability. All singlet and triplet excitons generated under the condition of electric excitation can realize ECL luminescence through TADF form, ECL performance is excellent, and luminous efficiency is high.
The foregoing examples are illustrative of the present invention and are not intended to be limiting, and other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principles of the invention are intended to be equivalent in scope.
Claims (7)
1. A nanomaterial characterized in that: the nanomaterial comprises a core and a shell;
the inner core is made of a heat-activated delayed fluorescent material; the shell layer is a surfactant;
the thermal activation delay fluorescent material is a compound with a structure shown in a formula (I);
（Ⅰ）；
in the formula (I), R 1 、R 2 Independently selected from C2-C8 alkyl groups; r is R 3 、R 4 Independently selected from C4-C10 alkyl groups; r is R 5 、R 6 Independently selected from C1-C6 alkyl; n is a positive integer of 2 to 250;
the surfactant comprises at least one of polystyrene maleic anhydride, polybutene maleic anhydride, polystyrene sulfonic acid and polystyrene acrylic acid.
2. The nanomaterial of claim 1, characterized in that: the mass ratio of the inner core to the shell layer is (0.1-5): 1.
3. a method for preparing a nanomaterial according to any of claims 1-2, characterized in that: the method comprises the following steps:
and mixing the thermal activation delay fluorescent material with a surfactant for reaction to obtain the nano material.
4. A method of preparation according to claim 3, characterized in that: the reaction includes reprecipitation.
5. Use of the nanomaterial of any of claims 1-2 in the field of biosensing for non-disease diagnostic purposes.
6. An aqueous phase electrochemical luminescence sensor, characterized in that: the aqueous phase electrochemical luminescence sensor comprising the nanomaterial of any of claims 1-2.
7. A method for detecting dopamine, which is characterized in that: the method comprises the following steps: the detection of dopamine-containing solutions using the aqueous electrochemical luminescence sensor of claim 6, wherein the detection method is used for non-disease diagnostic purposes.
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