CN116514651B - Amphiphilic aggregation-induced emission material fluorescent probe and application thereof - Google Patents
Amphiphilic aggregation-induced emission material fluorescent probe and application thereof Download PDFInfo
- Publication number
- CN116514651B CN116514651B CN202310744554.1A CN202310744554A CN116514651B CN 116514651 B CN116514651 B CN 116514651B CN 202310744554 A CN202310744554 A CN 202310744554A CN 116514651 B CN116514651 B CN 116514651B
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- fentanyl
- norfentanyl
- cooch
- emission material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 41
- 239000000463 material Substances 0.000 title claims abstract description 22
- 238000004220 aggregation Methods 0.000 title claims abstract description 17
- 230000002776 aggregation Effects 0.000 title claims abstract description 17
- 229960002428 fentanyl Drugs 0.000 claims abstract description 45
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims abstract description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 31
- 238000001514 detection method Methods 0.000 claims abstract description 29
- PMCBDBWCQQBSRJ-UHFFFAOYSA-N norfentanyl Chemical group C=1C=CC=CC=1N(C(=O)CC)C1CCNCC1 PMCBDBWCQQBSRJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 210000002966 serum Anatomy 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000003651 drinking water Substances 0.000 claims abstract description 8
- 235000020188 drinking water Nutrition 0.000 claims abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000523 sample Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000002189 fluorescence spectrum Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 239000012046 mixed solvent Substances 0.000 claims description 10
- 239000012086 standard solution Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000011534 incubation Methods 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- HXOFRBVHQQOXNL-UHFFFAOYSA-N phenyl(trifluoromethoxy)borinic acid Chemical compound FC(F)(F)OB(O)C1=CC=CC=C1 HXOFRBVHQQOXNL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940095102 methyl benzoate Drugs 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- JPGRSTBIEYGVNO-UHFFFAOYSA-N methyl 4-ethynylbenzoate Chemical compound COC(=O)C1=CC=C(C#C)C=C1 JPGRSTBIEYGVNO-UHFFFAOYSA-N 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 abstract description 3
- 230000001965 increasing effect Effects 0.000 abstract description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 2
- 238000006073 displacement reaction Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 238000011896 sensitive detection Methods 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000010791 quenching Methods 0.000 description 6
- 230000000171 quenching effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 229930182851 human metabolite Natural products 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 230000009323 psychological health Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- -1 serum Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/74—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen having unsaturation outside the aromatic rings
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention relates to an amphiphilic aggregation-induced emission material fluorescent probe and application thereof. According to the invention, tetraphenylbutadiene is used as a parent nucleus structure, and trifluoromethyl and carboxyl are modified on the parent nucleus by adopting a palladium-catalyzed Suzuki coupling reaction, so that Stokes displacement is increased, and the specific recognition capability of fentanyl/nor-fentanyl is enhanced; and the amphiphilic function improves the application of the polymer interference resistance in actual samples. The method has rapid and sensitive detection capability on the fentanyl in the drinking water solution and the norfentanyl in the serum, and has low detection limit.
Description
Technical Field
The invention belongs to the technical field of detection and fluorescent probe, and particularly relates to an amphiphilic aggregation-induced emission material fluorescent probe and application thereof.
Background
At present, the problem of abuse of new psychoactive substances of third-generation drugs represented by fentanyl internationally is remarkable, and physical and psychological health of people and national social stability are seriously threatened. Fentanyl (Fentanyl) was first studied as an analgesic, and its anesthetic and analgesic effects were about 50-100 times that of morphine, and about 2 mg was considered fatal. Meanwhile, due to the characteristics of high addiction, low price, high production efficiency, capability of camouflaging into drink or food selling on the internet and the like, the fentanyl is widely abused after flowing into the drug market, and serious challenges are brought to international forbidden poison and social public safety. In addition, after the human body ingests the fentanyl, the fentanyl can be converted into main metabolites through in-vivo metabolism in a short time: n-dealkylation product norfentanyl (norfentanyl). Therefore, a rapid detection method is needed to dynamically, qualitatively and quantitatively monitor the trace amount of fentanyl and the human metabolite norfentanyl.
In recent years, some on-site rapid detection technologies such as immune test strip detection are used for fentanyl detection, but false positives are easy to occur, and quantitative detection cannot be performed. When the surface enhanced raman spectroscopy sensor, the proton mobility spectrometer and the paper spray mass spectrometer are used for detecting the fentanyl substance in the mixed drug, a larger sample amount is usually required, and the analysis result can be influenced along with the fluctuation of the external environment. The fluorescent probe detection tool has the advantages of dynamic visualization, high sensitivity, strong selectivity and the like, and is paid more attention and greatly developed.
Therefore, in order to solve the above limitations, the present invention provides an amphiphilic aggregation-induced emission material TP-CF with tetraphenylbutadiene as a central substrate 3 The synthetic method of-COOH, the synthesized material prepares the fluorescent probe through condition optimization, can be applied to qualitative and quantitative detection of the fentanyl in drinking water and the norfentanyl in serum, and provides new technical dependence and support for on-site rapid detection of the fentanyl.
Disclosure of Invention
In order to solve the defects that the prior art of the fentanyl norfentanyl detection technology cannot meet the actual requirements and cannot realize on-site rapid visual detection, the detection sensitivity is not high enough and the selectivity is not strong enough, the invention adopts tetraphenylbutadiene as a parent nucleus structure, and uses palladium to catalyze a Suzuki coupling reaction to modify trifluoromethyl and carboxyl on the parent nucleus, thereby not only increasing Stokes displacement and enhancing the specificity recognition capability of fentanyl/norfentanyl; and the amphiphilic function improves the application of the polymer interference resistance in actual samples. The method has rapid and sensitive detection capability on the fentanyl in the drinking water solution and the norfentanyl in the serum, and has low detection limit.
The invention solves the technical problems by the following technical proposal:
the first object of the invention is to provide an amphiphilic aggregation-induced emission material fluorescent probe, which comprises a compound shown in a formula (I):
(I)
the aggregation-induced emission material fluorescent probe has hydrophilic and lipophilic amphiphilicity, and improves the anti-interference capability of the fluorescent probe in detection of practical samples such as aqueous solution, serum and the like.
Further, the amphiphilic aggregation-induced emission material fluorescent probe comprises a compound shown in a formula (I) and a solvent, wherein the solvent is a mixed solvent of an organic solvent and water, and the organic solvent is mutually soluble with the water; further, the concentration of the compound represented by the formula (I) is 5 to 50 mg/L, preferably 10 to 20 mg/L.
Further, the organic solvent is selected from at least one of tetrahydrofuran, methanol and ethanol; wherein water accounts for 60-99% of the volume of the mixed solvent.
The applicant finds that the solution system of the fluorescent probe is a mixed solvent of tetrahydrofuran and water according to the proportion, the fluorescence quenching rate after the reaction with the object to be detected is highest, and the fluorescent probe is suitable for being applied to detection as the fluorescent probe.
Further, the synthetic route of the compound represented by formula (I) is as follows:
。
further, the compound represented by the formula (I) is produced by a production method comprising the steps of:
(1) Toluene and acetonitrile are taken to be added into a flask, 4-ethynyl methyl benzoate, palladium chloride and copper bromide serving as catalysts are added into the solution to react under stirring at room temperature in dark place, decompression suction filtration is carried out, the filtrate is rotationally evaporated, concentrated and dried, and the intermediate TP-COOCH is obtained after purification 3 -Br；
(2) The solvent is a mixed solvent of toluene and methanol, so that the reaction system is anhydrous and oxygen-free, and then the trifluoromethyl phenylboronic acid and TP-COOCH are added 3 -Br、Pd(PPh 3 ) 4 And carbonate, heat and stirAnd refluxing, cooling to room temperature after the reaction is finished, and post-treating to obtain an intermediate product TP-CF 3 -COOCH 3 ；
(3) TP-CF 3 -COOCH 3 Adding into tetrahydrofuran, stirring, hydrolyzing under alkali condition to obtain crude product sodium salt, adding acid for acidification, precipitating precipitate, pressure filtering, recrystallizing crude product to obtain powder solid TP-CF 3 -COOH, i.e. a compound of formula (I).
Further, in the step (1), the reaction time is detected by TLC (thin layer chromatography) plate under stirring at room temperature in a dark place, the disappearance of the raw material points indicates the end of the reaction, and the reaction time is generally 8-12h; the purification is to obtain solid n-hexane recrystallization through column chromatography purification and separation by using methylene dichloride/petroleum ether (volume ratio is 1:2-5) as eluent.
Further, in the step (1), the volume ratio of toluene to acetonitrile is 40-60:1, preferably 45-50:1, a step of; the mass ratio of the methyl 4-ethynyl benzoate to the palladium chloride to the copper bromide is 20-30:2-3:100-150.
In the step (2), in order to ensure no water and oxygen in the reaction process, firstly, degassing a mixed solvent of toluene and methanol by using a liquid nitrogen freezing solution, vacuumizing, repeating the process for 3 times, and then introducing nitrogen, wherein the volume ratio of toluene to ethanol is 1-3:1.
Further, in the step (2), trifluoromethylphenylboronic acid and TP-COOCH are mixed 3 -Br、Pd(PPh 3 ) 4 And the mass ratio of carbonate is 250-300:200-300:50-90:380-440.
Further, in the step (2), the heating and stirring temperature is 60-85 ℃, preferably 70-80 ℃; heating and stirring for 12-30h, preferably 20-24h; the post-treatment is reduced pressure suction filtration, the collected filtrate is washed for 1 to 3 times by dilute hydrochloric acid solution, carbonate is removed, and then anhydrous magnesium sulfate is added for dewatering and drying. Suction filtration is carried out, and the obtained filtrate is subjected to reduced pressure distillation and concentration; the concentrated filtrate was separated using column chromatography (dichloromethane/n-hexane=1-2:1-2), and the resulting solid was recrystallized from n-hexane and filtered off with suction to give a powder TP-CF 3 -COOCH 3 . The carbonate is at least one of sodium carbonate and potassium carbonate.
Further, in the step (3), the hydrolysis is carried out at 60-80 ℃ under alkaline conditions for 12-30 hours, preferably 20-24 hours; the alkaline condition is that NaOH and/or KOH are added, and the addition of acid is that dilute hydrochloric acid (5-15%) is added.
The second object of the invention is to provide the use of the amphiphilic aggregation-inducing luminescent material fluorescent probe in the detection of fentanyl and/or norfentanyl.
A third object of the present invention is to provide a method for detecting fentanyl and/or norfentanyl, comprising the steps of:
(S1) mixing the amphiphilic aggregation-induced emission material fluorescent probe with fentanyl standard solutions with different concentrations or with norfentanyl standard solutions with different concentrations, incubating, and then performing fluorescence spectrum test to establish a standard curve;
and (S2) mixing the amphiphilic aggregation-induced emission material fluorescent probe with a sample to be detected, incubating, and then performing a fluorescence spectrum test, and calculating according to the fluorescence intensity and a standard curve to obtain the concentration of the fentanyl and/or norfentanyl in the sample to be detected.
Further, the incubation condition is that the incubation is performed at 25-30 ℃ for 30-60s.
Further, the sample to be detected is drinking water, serum, solid powder and the like; further, the serum is human serum, bovine serum, porcine serum, chicken serum or murine serum.
The invention has the excellent effects that the fluorescent probe comprising the compound shown in the formula (I) is prepared for detecting the fentanyl and/or norfentanyl in the sample, and has the advantages of quick detection time, low detection limit and high sensitivity; and can realize the quick visual detection in the field.
Drawings
FIG. 1 shows the TP-COOCH obtained in the examples 3 -Br(A)、TP-CF 3 -COOCH 3 (B)、TP-CF 3 -infrared spectrum of COOH (C);
FIG. 2 is the product TP-CF of example 1 3 -nuclear magnetic hydrogen and mass spectra of COOH;
FIG. 3 is a TP-CF 3 -fluorescence spectrum of COOH;
FIG. 4 is a TP-CF 3 -fluorescence quenching rate plot of COOH;
FIG. 5 is a fluorescence spectrum after incubation of different standard concentrations of fentanyl solution with fluorescent probes;
FIG. 6 is a standard curve of a fentanyl solution;
FIG. 7 is a fluorescence spectrum after incubation of different standard concentrations of norfentanyl serum solution and fluorescent probe;
FIG. 8 is a standard curve of norfentanyl serum solution;
fig. 9 is a schematic diagram of the rapid qualitative detection of trace amounts of fentanyl in drinking water on site.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. The following examples facilitate a better understanding of the present invention, but are not intended to limit the same. The experimental methods in the following examples are conventional methods unless otherwise specified.
Example 1
(1) TP-COOCH 3 Preparation of Br: 25mL of toluene and 0.5: 0.5 mL acetonitrile are added into a 100 mL flask, 480 mg of 4-ethynyl methyl benzoate, 40: 40 mg palladium bromide and 2g of copper bromide are added into the solution, the mixture is stirred for 12 hours at room temperature in the dark, a TLC (thin layer chromatography) point plate is used for detection, the disappearance of a raw material point is the end of the reaction, then the reaction is reduced pressure and suction filtration is carried out, the catalyst is filtered, concentrated and dried by rotary evaporation, dichloromethane/petroleum ether (volume ratio is 1:2) is used as eluent, solid is obtained by purification and separation of column chromatography, and after normal hexane is recrystallized, the target product TP-COOCH is obtained 3 -Br。
(2) TP-CF 3 -COOCH 3 Is prepared from the following steps: degassing the liquid nitrogen freezing solution to obtain a mixed solvent of 30 mL toluene and 10 mL methanol, vacuumizing, repeating the process for 3 times, and sequentially introducing 284.89mg of trifluoromethyl phenylboronic acid and 240 mg of TP-COOCH after introducing nitrogen 3 Br, pd (PPh) 61.25. 61.25 mg 3 ) 4 Adding 414.63 mg potassium carbonate into round bottom flask, heating to 80deg.C, stirring, reflux reacting for 24 hr, cooling to room temperature, vacuum filtering, washing the filtrate with 5% diluted hydrochloric acid solution for three times, and removing carbonAnd adding anhydrous magnesium sulfate to remove water, drying, filtering, and concentrating the obtained filtrate by reduced pressure distillation. The concentrated filtrate was separated by column chromatography (volume ratio of dichloromethane/n-hexane 1:1), and the obtained solid was recrystallized from n-hexane and filtered by suction to obtain a powder TP-CF 3 -COOCH 3 。
(3)TP-CF 3 Preparation of-COOH: 61.5mg of TP-CF 3 -COOCH 3 Adding into a round bottom flask, adding 10 mL tetrahydrofuran solution, stirring uniformly, adding 10 ml of 0.8mM NaOH aqueous solution into the flask, stirring uniformly, heating to 80 ℃, reacting for 24 hours, detecting a point plate, eliminating a raw material point, and ending the reaction. After stopping the reaction, after the solution was cooled to room temperature, the solvent was distilled off under reduced pressure to obtain the sodium salt of the crude product. Then, a sufficient amount of 5% diluted hydrochloric acid solution is dripped into the obtained sodium salt, acidizing is carried out, precipitation is carried out, the crude product is obtained, pressurization and suction filtration are carried out, normal hexane is recrystallized, and finally, the powder solid TP-CF is obtained 3 -COOH。
FIG. 1 shows the TP-COOCH obtained in the examples 3 -Br(A)、TP-CF 3 -COOCH 3 (B)、TP-CF 3 -infrared spectrum of COOH (C). It can be seen that the prepared TP-COOCH 3 -Br and TP-CF 3 -COOCH 3 Has obvious signal peak, and after ester group hydrolysis, TP-CF 3 -COOH in infrared spectrum 3300 cm -1 The vibration peak of-O-H appears, indicating that TP-CF has been synthesized 3 -COOH material.
FIG. 2 is the product TP-CF 3 -nuclear magnetic hydrogen and mass spectra of COOH, wherein a is hydrogen spectrum: 1 H NMR (600 MHz, THF-d8) δ 10.85 (s, 2H), 7.90 (d,J= 8.1 Hz, 4H), 7.79 (d,J= 8.0 Hz, 4H), 7.54 (d,J= 7.9 Hz, 4H), 7.23 (d,J=8.2 Hz, 4H), 6.790 (s, 2H). B is the product TP-CF 3 -high resolution mass spectrum of COOH.
Example 2
TP-CF prepared in the examples 3 -COOH is dissolved in mixed solvents of tetrahydrofuran and water in different volume ratios to obtain fluorescent probe dispersion liquid, the dispersion is carried out under the ultrasonic condition, the ultrasonic condition is 40-100 KHz, and the ultrasonic time is 30min. FIG. 3 is a fluorescent light thereofA spectrum. As can be seen, the prepared TP-CF 3 the-COOH material was not fluorescent after being dissolved in tetrahydrofuran, and the fluorescence intensity of the solution gradually increased with the increase of the water content in the tetrahydrofuran-water solution, which indicates that the material has aggregation-induced emission properties.
To obtain the best fluorescent probe, the material is first dispersion ratio optimized. The fluorescence quenching rate (C) was calculated as C= (F0-F)/F0.times.100% based on the Stern-Volmer equation, where F and F0 represent TP-CF with and without addition of fentanyl, respectively 3 Fluorescence intensity of-COOH. By measuring TP-CF in different water volumes to which the same dose of fentanyl was added 3 -COOH material fluorescence intensity, and calculating the corresponding fluorescence quenching rate. FIG. 4 is a TP-CF 3 -fluorescence quenching rate plot of COOH. Wherein when tetrahydrofuran/water volume is 1:4, the fluorescence quenching rate is the highest, so that the THF/water ratio is the optimal ratio of 1:4 by volume for practical application.
Example 3
(1) Preparation of TP-CF 3 -COOH fluorescent probe:
1 mg example 1 was taken to give TP-CF 3 adding-COOH into 2 ml tetrahydrofuran, adding 8 ml ultrapure water after the solid is fully dissolved, and performing ultrasonic treatment at normal temperature for 30 minutes to obtain 100 mg/L fluorescent probe stock solution. Each time, the mixture solution (THF/water 1:4) with the same volume ratio is diluted to 10 mg/L;
(2) Preparing a fentanyl standard solution:
preparing a standard solution of fentanyl with ultrapure water at concentrations of 10 ng/L, 100 ng/L, 1 μg/L, 10 μg/L, 100 μg/L and 1 mg/L, respectively;
(3) Establishing a standard working curve:
the measurement conditions of the portable enzyme-labeled instrument for measuring fluorescence spectrum are as follows: the excitation wavelength was 350 nm and the slit width was 20 nm. 180 ul of TP-CF (10 mg/L) 3 the-COOH fluorescent probes were mixed with different concentrations of fentanyl standard solution 20ul and incubated at 25℃for 30 s for fluorescence spectrometry.
FIG. 5 is a fluorescence spectrum after incubation of different standard concentrations of fentanyl solution and fluorescent probe, as can be seen, with fentanyl concentrationIncrease, TP-CF 3 The fluorescence intensity of the-COOH probe was significantly reduced. As shown in FIG. 6, the relative fluorescence intensity of the probe and the concentration of fentanyl are in good linear relation, and Y=0.1255x+0.1398, R 2 =0.9850, Y is the relative fluorescence intensity change value, expressed by the formula y= (I) 0 Calculated as-I)/I x 100%, where I 0 For the fluorescence intensity before the reaction of the sample to be detected and the fluorescent probe mixed solution, I is the fluorescence intensity after the reaction, x is the fentanyl concentration, the unit is ng/L, the minimum detection limit of the probe to the fentanyl is 0.2337 ng/L according to the standard deviation delta=1.1% obtained by 10 times of measurement, and the detection range is 10 ng/L-1 mg/L.
Example 4
(1) Preparation of TP-CF 3 -COOH fluorescent probe:
1 mg example 1 was taken to give TP-CF 3 adding-COOH into 2 ml tetrahydrofuran, adding 8 ml ultrapure water after the solid is fully dissolved, and performing ultrasonic treatment at normal temperature for 30 minutes to obtain 100 mg/L fluorescent probe stock solution. At each use, the mixture solution (THF/water 1:4) with the same volume ratio is diluted to 10 mg/L;
(2) Preparing a norfentanyl standard solution:
preparing norfentanyl standard solution with fetal bovine serum at the concentration of 10 ng/L, 100 ng/L, 1 μg/L, 10 μg/L, 100 μg/L and 1 mg/L respectively;
(3) Establishing a standard working curve
Taking 200ul of the serum sample, adding 600ul of tetrahydrofuran, swirling for 30 s, centrifuging at 14000 rpm and 4 ℃ for 5min, taking supernatant 20ul, adding 180 ul of TP-CF 3 In the-COOH probe, after incubation at 25℃for 30 s, fluorescence intensity measurement was performed with a portable microplate reader. The measurement conditions of the portable enzyme-labeled instrument for measuring fluorescence spectrum are as follows: the excitation wavelength was 350 nm and the slit width was 20 nm.
FIG. 7 is a fluorescence spectrum after incubation of different standard concentrations of norfentanyl serum solution and fluorescent probe, as shown by TP-CF as the concentration of norfentanyl increases 3 The fluorescence intensity of the-COOH probe was significantly reduced. FIG. 8 is a standard curve of norfentanyl serum solution, relative fluorescence of probesIntensity is in good linear relation with norfentanyl concentration, y=0.1470x+0.2669, r 2 =0.9867, Y is the relative fluorescence intensity change value, expressed by the formula y= (I) 0 Calculated as-I)/I, wherein I 0 The method is characterized in that the fluorescent intensity before the reaction of the sample to be detected and the fluorescent probe mixed solution is calculated, wherein I is the fluorescent intensity after the reaction, x is the concentration of the norfentanyl, the unit is ng/L, the minimum detection limit of the probe on the norfentanyl is 0.2677 ng/L according to the standard deviation delta=1.16% obtained by 10 times of measurement, and the detection range is 10 ng/L-1 mg/L.
Example 5
(1) Ultraviolet lamp rapid detection trace fentanyl:
fig. 9 is a schematic diagram of the rapid qualitative detection of trace amounts of fentanyl in drinking water on site. FIG. 9 (A) shows a TP-CF prepared in example 3 by adding 200ul of 50 ng/L aqueous fentanyl to 800 ul and 180 ul 3 In the COOH fluorescent probe liquid (10 mg/L), after the whole ultraviolet lamp irradiates for 30 seconds, the fluorescence of the solution is obviously reduced, and the method can be used for rapidly and qualitatively detecting the trace amount of fentanyl in the drinking water.
(2) The enzyme-labeled instrument quantitatively detects fentanyl:
fig. 9 (B) exemplifies: taking 20ul of 1000 ug/ml of fentanyl standard solution (methanol solution) into a sample injection vial, blowing nitrogen for 5 minutes, then adding water to the solution volume of 2 ml, uniformly mixing and swirling for 1 minute; taking 20ul of the solution, adding water to the volume of 8 ml, and swirling for 30 seconds; 20ul of this solution was taken and added to 180 ul of the TP-CF prepared in example 3 3 in-COOH fluorescent probe liquid (10 mg/L). Before the reaction of the 20ul sample to be measured and the fluorescent probe mixed solution (I) 0 ) After (I), the relative fluorescence intensity change value (I) is calculated 0 -I)/i×100% = (1091-829.5)/829.5 ×100% = 31.53%, and comparing the standard curve obtained in example 3, the content of fentanyl in the sample to be tested is 25.03ng/L.
Claims (10)
1. A compound for an amphiphilic aggregation-induced emission material fluorescent probe, which is characterized by having a structure shown in a formula (I):
(I)。
2. the amphiphilic aggregation-induced emission material fluorescent probe is characterized by comprising a compound shown in a formula (I) and a solvent, wherein the solvent is a mixed solvent of an organic solvent and water, and the organic solvent is mutually soluble with the water; the concentration of the compound shown in the formula (I) is 5-50 mg/L.
3. The fluorescent probe according to claim 1, wherein the concentration of the compound represented by formula (I) is 10 to 20 mg/L.
4. The fluorescent probe according to claim 2, wherein the organic solvent is at least one selected from tetrahydrofuran, methanol, and ethanol; wherein water accounts for 60-99% of the volume of the mixed solvent.
5. The method for preparing a compound according to claim 1, wherein the synthetic route is as follows:
。
6. the method of manufacturing according to claim 5, comprising the steps of:
(1) Toluene and acetonitrile are taken to be added into a flask, 4-ethynyl methyl benzoate, catalyst palladium chloride and copper bromide are then added into the solution to be stirred at room temperature in dark for reaction, decompression suction filtration is carried out, the filtrate is rotationally evaporated, concentrated and dried, and the intermediate product TP-COOCH is obtained after purification 3 -Br；
(2) The solvent is a mixed solvent of toluene and methanol, so that the reaction system is anhydrous and oxygen-free, and then the trifluoromethyl phenylboronic acid and TP-COOCH are added 3 -Br、Pd(PPh 3 ) 4 And carbonate, heating, stirring and refluxing, cooling to room temperature after the reaction is finished, and performing post-treatment to obtain an intermediate product TP-CF 3 -COOCH 3 ；
(3) TP-CF 3 -COOCH 3 Adding into tetrahydrofuran, stirring, hydrolyzing under alkali condition to obtain sodium and/or potassium salt of crude product, adding acid for acidification, precipitating precipitate, filtering under pressure, recrystallizing crude product to obtain powder solid TP-CF 3 -COOH, i.e. a compound of formula (I).
7. The preparation method according to claim 6, wherein in the step (1), the mass ratio of the methyl 4-ethynylbenzoate, the palladium chloride and the copper bromide is 20-30:2-3:100-150; and/or
In the step (2), trifluoromethyl phenylboronic acid, TP-COOCH 3 -Br、Pd(PPh 3 ) 4 And the mass ratio of carbonate is 250-300:200-300:50-90:380-440; and/or
In the step (3), the hydrolysis is carried out at 60-80 ℃ under alkaline conditions, and the hydrolysis time is 20-24 hours; the alkaline condition is that NaOH and/or KOH are added, and the addition of acid is that dilute hydrochloric acid is added.
8. Use of the amphiphilic aggregation-inducing emission material fluorescent probe according to any one of claims 2-4 for the detection of fentanyl and/or norfentanyl.
9. A method of detecting fentanyl and/or norfentanyl, comprising the steps of:
(S1) mixing the fluorescent probe of the amphiphilic aggregation-induced emission material according to any one of claims 2-4 with a standard solution of fentanyl with different concentrations or with a standard solution of norfentanyl with different concentrations, incubating, and performing a fluorescence spectrum test to establish a standard curve;
and (S2) mixing the amphiphilic aggregation-induced emission material fluorescent probe with a sample to be detected, incubating, and performing a fluorescence spectrum test, and calculating according to the fluorescence intensity and a standard curve to obtain the concentration of the fentanyl or norfentanyl in the sample to be detected.
10. The method of claim 9, wherein the incubation conditions are 25-30 ℃ for 30-60s;
the sample to be measured is drinking water, serum and solid powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310744554.1A CN116514651B (en) | 2023-06-25 | 2023-06-25 | Amphiphilic aggregation-induced emission material fluorescent probe and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310744554.1A CN116514651B (en) | 2023-06-25 | 2023-06-25 | Amphiphilic aggregation-induced emission material fluorescent probe and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116514651A CN116514651A (en) | 2023-08-01 |
| CN116514651B true CN116514651B (en) | 2023-09-05 |
Family
ID=87396197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310744554.1A Active CN116514651B (en) | 2023-06-25 | 2023-06-25 | Amphiphilic aggregation-induced emission material fluorescent probe and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116514651B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005255562A (en) * | 2004-03-09 | 2005-09-22 | Kyoto Univ | Multi-substituted butadiene and selective method for producing the same |
| CN104017222A (en) * | 2013-03-01 | 2014-09-03 | 中国科学院理化技术研究所 | Dendrimer externally modified with aggregation-induced emission enhanced chromophore as well as preparation method and application thereof |
| CN104326861A (en) * | 2014-11-25 | 2015-02-04 | 广东海洋大学 | Preparation method of 1,3-diene derivatives having aggregation-induced emission property |
| CN104327842A (en) * | 2014-10-09 | 2015-02-04 | 北京理工大学 | Fluorescent material for five-membered heterocyclic compound specific detection and preparation method |
| CN105713598A (en) * | 2016-03-07 | 2016-06-29 | 南方医科大学 | Application of pentasubstituted tetrahydropyrimidines derivative to preparation of material with fluorescent piezallochromy property |
| CN115210557A (en) * | 2019-10-21 | 2022-10-18 | 韦里特克美国有限公司 | Fentanyl analogue detection method and kit thereof |
| CN116178092A (en) * | 2022-07-26 | 2023-05-30 | 苏州大学 | Preparation method of 1, 4-tetraphenyl-1, 3-butadiene and derivatives thereof |
-
2023
- 2023-06-25 CN CN202310744554.1A patent/CN116514651B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005255562A (en) * | 2004-03-09 | 2005-09-22 | Kyoto Univ | Multi-substituted butadiene and selective method for producing the same |
| CN104017222A (en) * | 2013-03-01 | 2014-09-03 | 中国科学院理化技术研究所 | Dendrimer externally modified with aggregation-induced emission enhanced chromophore as well as preparation method and application thereof |
| CN104327842A (en) * | 2014-10-09 | 2015-02-04 | 北京理工大学 | Fluorescent material for five-membered heterocyclic compound specific detection and preparation method |
| CN104326861A (en) * | 2014-11-25 | 2015-02-04 | 广东海洋大学 | Preparation method of 1,3-diene derivatives having aggregation-induced emission property |
| CN105713598A (en) * | 2016-03-07 | 2016-06-29 | 南方医科大学 | Application of pentasubstituted tetrahydropyrimidines derivative to preparation of material with fluorescent piezallochromy property |
| CN115210557A (en) * | 2019-10-21 | 2022-10-18 | 韦里特克美国有限公司 | Fentanyl analogue detection method and kit thereof |
| CN116178092A (en) * | 2022-07-26 | 2023-05-30 | 苏州大学 | Preparation method of 1, 4-tetraphenyl-1, 3-butadiene and derivatives thereof |
Non-Patent Citations (1)
| Title |
|---|
| Tuning the Luminescence of Metal-Organic Frameworks for Detection of Energetic Heterocyclic Compounds;Guo, Yuexin 等;J. Am. Chem. Soc.;第136卷(第44期);15485-15488 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116514651A (en) | 2023-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Polydiacetylene-based sensor for highly sensitive and selective Pb2+ detection | |
| Chen et al. | A highly selective naked-eye and fluorescent probe for fluoride ion based on 1, 8-naphalimide and benzothizazole | |
| WO2020228640A1 (en) | Zinc ion fluorescent probe compound, preparation method therefor and use thereof | |
| Cheng et al. | New fluorescent probes for mercury (II) with simple structure | |
| Zhao et al. | Design and preparation of poly (tannic acid) nanoparticles with intrinsic fluorescence: a sensitive detector of picric acid | |
| Nie et al. | Visual and reversible detection of cyanide ions in protic solvents by a novel colorimetric receptor | |
| WO2019196022A1 (en) | 1,8-naphthalimide derivative, preparation method therefor and use thereof | |
| Wang et al. | A Schiff base fluorescent chemsensor for the double detection of Al3+ and PPi through aggregation induced emission in environmental physiology | |
| Ren et al. | Spirohydrazine rhodamine as a fluorescent chemodosimeter for the selective detection of Cu (II) ions and its application in live cell imaging | |
| CN105294539A (en) | Aluminum ion fluorescent probe compound and preparation method thereof | |
| Kai et al. | A highly selective colorimetric and ratiometric fluorescent chemodosimeter for detection of fluoride ions based on 1, 8-naphthalimide derivatives | |
| Sun et al. | Highly selective fluorescence sensor sensing benzo [a] pyrene in water utilizing carbon dots derived from 4-carboxyphenylboronic acid | |
| CN112341463B (en) | Purine parent-based fluorescent probe compound and preparation method and application thereof | |
| EP3028051B1 (en) | Water soluble polyfluorene functionalized with glucuronic acid useful in bilirubin sensing | |
| Ma et al. | A novel fluorescence and surface-enhanced Raman scattering dual-signal probe for pH sensing based on Rhodamine derivative | |
| Chen et al. | A bio-bar-code photothermal probe triggered multi-signal readout sensing system for nontoxic detection of mycotoxins | |
| CN108088828B (en) | Double-column aromatic mercury ion fluorescent sensor and preparation and application thereof | |
| Yang et al. | Liquid-liquid extraction and purification of oil red O derived nitrogen-doped highly photoluminescent carbon dots and their application as multi-functional sensing platform for Cu2+ and tetracycline antibiotics | |
| CN116514651B (en) | Amphiphilic aggregation-induced emission material fluorescent probe and application thereof | |
| CN106008435B (en) | One kind is used for Au3+Fluorescence Increasing type fluorescence probe of detection and preparation method thereof | |
| CN105968098B (en) | A kind of quinoline substituted containing carbazole, benzimidazole and its preparation method and application | |
| CN113121589B (en) | 1, 8-naphthalimide-based organic material, organic-inorganic hybrid nano material, preparation method and application | |
| CN113666937B (en) | Near-infrared fluorescent probe for detecting zinc ions and preparation method and application thereof | |
| CN106008971B (en) | Preparation method of fluorescent probe polyimide | |
| CN110283213B (en) | Colorimetric probe capable of detecting bisulfite and mercury ions, and synthesis method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |