CN109406474A - A kind of aggregation-induced emission-molecular engram fluorescent optical sensor preparation method and application detecting rhodamine B - Google Patents
A kind of aggregation-induced emission-molecular engram fluorescent optical sensor preparation method and application detecting rhodamine B Download PDFInfo
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- CN109406474A CN109406474A CN201811354429.5A CN201811354429A CN109406474A CN 109406474 A CN109406474 A CN 109406474A CN 201811354429 A CN201811354429 A CN 201811354429A CN 109406474 A CN109406474 A CN 109406474A
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229940043267 rhodamine b Drugs 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 230000002776 aggregation Effects 0.000 title claims abstract description 18
- 238000004220 aggregation Methods 0.000 title claims abstract description 18
- 230000003287 optical effect Effects 0.000 title description 14
- 238000000034 method Methods 0.000 claims abstract description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 15
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 11
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960005080 warfarin Drugs 0.000 claims abstract description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 10
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000012673 precipitation polymerization Methods 0.000 claims abstract description 6
- 238000001917 fluorescence detection Methods 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000010828 elution Methods 0.000 claims description 21
- FHQUGPIKNGYMST-UHFFFAOYSA-N [4-(1,2,2-triphenylethenyl)phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=CC=C(C=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 FHQUGPIKNGYMST-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000002189 fluorescence spectrum Methods 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 239000003480 eluent Substances 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000005284 excitation Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 5
- ZSZOSPYBNNWIIN-UHFFFAOYSA-N 4-(1,2,2-triphenylethenyl)phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 ZSZOSPYBNNWIIN-UHFFFAOYSA-N 0.000 claims description 4
- 238000000944 Soxhlet extraction Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 229920000344 molecularly imprinted polymer Polymers 0.000 claims description 3
- 239000012488 sample solution Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims 5
- COIQUVGFTILYGA-UHFFFAOYSA-N (4-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(O)C=C1 COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 claims 2
- NZHXEWZGTQSYJM-UHFFFAOYSA-N [bromo(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 NZHXEWZGTQSYJM-UHFFFAOYSA-N 0.000 claims 2
- 239000011259 mixed solution Substances 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 238000000967 suction filtration Methods 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 19
- 238000005516 engineering process Methods 0.000 abstract description 9
- 235000009467 Carica papaya Nutrition 0.000 abstract description 7
- 238000011084 recovery Methods 0.000 abstract description 7
- 235000013361 beverage Nutrition 0.000 abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 241000219173 Carica Species 0.000 abstract 1
- 238000007306 functionalization reaction Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000000523 sample Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 244000189799 Asimina triloba Species 0.000 description 6
- 235000006264 Asimina triloba Nutrition 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 dichloromethane Alkane Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
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- 239000011159 matrix material Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YYXFJSDMOVHLMJ-UHFFFAOYSA-N (4-hydroxyphenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(O)C=C1 YYXFJSDMOVHLMJ-UHFFFAOYSA-N 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 239000004218 Orcein Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- BWKJBUMGJDQICE-UHFFFAOYSA-N acetonitrile;2-methylprop-2-enoic acid Chemical compound CC#N.CC(=C)C(O)=O BWKJBUMGJDQICE-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明公开了一种检测罗丹明B的聚集诱导发光‑分子印迹荧光传感器的制备方法及应用，该方法是结合分子印迹技术和荧光检测技术，采用华法林为模板分子，α‑甲基丙烯酸为功能单体，乙二醇二甲基丙烯酸酯为交联剂，偶氮二异丁腈为引发剂，乙腈为溶剂，加入功能化AIE分子，采用沉淀聚合法合成AIE‑MIPs。本发明AIE‑MIPs不仅操作简便，使用有机试剂较少，且对罗丹明B具有较强的识别能力，并且在浓度范围为1×10‑5‑10×10‑5mol/L内线性关系良好。把AIE‑MIPs用于对实际样品木瓜干、芬达饮料进行加标回收实验，结果表明罗丹明B的回收率范围为96.2‑103.5％，相对标准偏差范围为1.5‑4.7％。这些数据表明了荧光检测技术与分子印迹技术相结合得到的AIE‑MIPs可应用于实际样品中罗丹明B的检测。
The invention discloses a preparation method and application of an aggregation-induced luminescence-molecular imprinted fluorescent sensor for detecting rhodamine B. The method combines molecular imprinting technology and fluorescence detection technology, adopts warfarin as a template molecule, α-methacrylic acid As a functional monomer, ethylene glycol dimethacrylate is a cross-linking agent, azobisisobutyronitrile is an initiator, acetonitrile is a solvent, and functionalized AIE molecules are added to synthesize AIE-MIPs by precipitation polymerization. The AIE-MIPs of the invention are not only easy to operate, use less organic reagents, but also have a strong ability to identify Rhodamine B, and have a good linear relationship in the concentration range of 1× 10-5-10×10-5 mol /L . The AIE‑MIPs were used in the spiked recovery experiments on the actual samples of dried papaya and Fanta beverages. The results showed that the recovery range of Rhodamine B was 96.2‑103.5%, and the relative standard deviation range was 1.5‑4.7%. These data demonstrate that AIE‑MIPs obtained by combining fluorescence detection technology with molecular imprinting technology can be applied to the detection of Rhodamine B in real samples.
Description
Technical field
The present invention relates to a kind of aggregation-induced emission-molecular engram fluorescent optical sensor preparation methods for detecting rhodamine B
And application, belong to rhodamine B technical field of analysis and detection.
Background technique
Rhodamine B is a kind of orchil of synthesis, has been used for fluorescent marker and edible pigment.But it is to people
Class and animal are all harmful, especially generate stimulation to skin, eyes and respiratory tract, belong to carcinogen.Therefore, forbid in food
Middle addition rhodamine B is as food additives.But bright-colored since rhodamine B is cheap, many businessmans are in order to save into
The bigger profit of this acquisition continues to use rhodamine B as food additives, this compromises the health of the mankind significantly.Detect Luo Dan
The conventional method of bright B has thin-layered chromatography and high performance liquid chromatography etc., and not only cost is very expensive for these methods, but also deposits
In cumbersome problem.And due to the complicated component of food, the content of rhodamine B is low in food, need to actual sample into
Row sample pretreatment, sample-pretreating method not only complex steps can generate a large amount of organic liquid waste, and lack selective absorption
Ability.Therefore, the rhodamine B established in a kind of simple and rapid method measurement actual sample is necessary.
Molecularly imprinted polymer (Molecular Imprinting Polymers, abbreviation MIPs) is a kind of using molecule
The polymer that engram technology is process, this technology make cavity and selected " template " molecule in polymeric matrix have parent
And power.The polymer not only has specific recognition capability, also has selective absorption.And MIPs also has the advantage that
One, the method for preparing MIPs is comparatively simple and economical, and most of MIPs are synthesized by substance law and precipitation polymerization method；The
Two, MIPs have good physics and chemical stability；Finally, MIPs can be used in severe chemical environment, do not lose
Absorption property.
Fluorescent optical sensor, which is commonly divided into, is quenched type fluorescent optical sensor, enhanced fluorescent optical sensor and Ratio-type fluorescence sense
Device three types.The difference of principle according to response, different types of sensor are also different to the response modes of different material.
Up to the present, most of fluorescent materials are all detected using single response signal, and this signal becomes vulnerable to fluorescence intensity
Change and the influence of the external factor such as environment and instrument efficiency.And ratio measure by comparing two fluorescence peaks ratio rather than
The absolute intensity at one peak obtains more accurate as a result, having the advantages that eliminating environment influences.
Since MIPs is polymer, belong to solid, thus find it is a kind of solid state issue intense fluorescence molecule be
It is very important.Aggregation-induced emission (Aggregation-induced Emission, abbreviation AIE) molecule issues strong in solid-state
Strong fluorescence, it is very useful for being introduced into MIPs.But there is presently no the reports for combining AIE with MIPs.
Summary of the invention
In view of the deficiencies of the prior art, the object of the present invention is to provide one kind using AIE molecule as fluorophor, is with MIPs
Recognition group, binding molecule engram technology and detection technique of fluorescence, using precipitation polymerization method, the aggregation of synthesis detection rhodamine B
Induced luminescence-molecular engram fluorescent optical sensor (AIE-MIPs) preparation method and application, gained AIE-MIPs have rhodamine B
There are stronger recognition capability and excellent selectivity.
To achieve the goals above, the technical scheme adopted by the invention is that:
A kind of aggregation-induced emission-molecular engram fluorescent optical sensor preparation method detecting rhodamine B, by functionalization
AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate is combined with molecularly imprinted polymer, using precipitation polymerization
Legal system obtains aggregation-induced emission-molecular engram fluorescent optical sensor AIE-MIPs.
Specifically, aggregation-induced emission-molecular engram fluorescent optical sensor of detection rhodamine B is the preparation method comprises the following steps: accurate
It weighs warfarin 0.8-1.2mmol to be placed in there-necked flask, addition 0.1-0.3g azodiisobutyronitrile, 150-200mL acetonitrile, then
5-15mmol α-methacrylic acid is added, 60-100mmol ethylene glycol dimethacrylate adds 0.01-0.05mmol function
AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate can be changed, ultrasonic vibration 15-30min dissolves it all,
Under conditions of 70-90 DEG C, mechanic whirl-nett reaction 8-12h is filtered, and is dried, elution.
Preferably, aggregation-induced emission-molecular engram fluorescent optical sensor of rhodamine B is detected the preparation method comprises the following steps: accurate
It weighs warfarin 1.0mmol to be placed in there-necked flask, 0.2g azodiisobutyronitrile is added, then 9mmol α-is added in 150mL acetonitrile
Methacrylic acid, 60mmol ethylene glycol dimethacrylate add 0.01mmol functionalization AIE molecule 4- (1,2,2- tri-
Phenyl vinyl) phenyl acrylate, ultrasonic vibration 15min, make its all dissolve, under conditions of 83 DEG C, mechanical stirring is anti-
8h is answered, is filtered, is dried, elution.
The method of elution are as follows: build soxhlet type apparatus, the mixed liquor of 200-300mL methanol and acetic acid is added, will synthesize
Good AIE-MIPs is wrapped with filter paper to be put into Soxhlet extraction device, after 90-100 DEG C of temperature control, elution 2-3 days, uses 100-
The pure methanol elution of 300mL, at regular intervals with the fluorescence spectrum of fluorescence detector measurement eluent, the fluorescence of warfarin molecule
Launch wavelength is 385nm, then illustrates that elution is clean without peak at this wavelength, is finally dried for standby.
The volume ratio of methanol and acetic acid is 4:1-6:1 in the mixed liquor of methanol and acetic acid.
Functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate the preparation method comprises the following steps:
(1) it weighs 1.5-2.5mmol triphen vinyl bromide to be put into round-bottomed flask, 2-3mmol 4- hydroxy benzenes boron is then added
Acid, 20-30mmol potassium carbonate, 0.05-0.10mmol tetra- (triphenyl phosphorus) palladium, 10-20mL water and 20-30mL tetrahydrofuran are taken out
Empty flask is simultaneously filled with nitrogen protection, reacts 12-24h under conditions of 75-95 DEG C；Products therefrom is filtered, filtrate is collected, with two
Organic phase is collected after chloromethanes extraction；After the drying of 5g anhydrous sodium sulfate is added, by pillar layer separation, functionalization AIE points are obtained
Sub- intermediate 4- (1,2,2- triphenyl vinyl) phenol；
(2) 3-5mmol functionalization AIE molecule intermediate is dissolved in 25mL methylene chloride, tri- second of 10-12mmol is added
Amine, and 8-10mmol acryloyl chloride is added dropwise, 4-6h is stirred at room temperature, is filtered, and vacuum distillation removes solvent, obtains functionalization
AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate crude product；By pillar layer separation, pure functionalization is obtained
AIE molecule.
Preferably, functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate the preparation method comprises the following steps:
(1) it weighs 2mmol triphen vinyl bromide to be put into round-bottomed flask, 2.4mmol 4- hydroxyl phenyl boric acid is then added,
20mmol potassium carbonate, 0.1mmol tetra- (triphenyl phosphorus) palladium, 15mL water and 25mL tetrahydrofuran evacuate flask and are filled with nitrogen guarantor
Shield, reacts 12h under conditions of 85 DEG C；Products therefrom is filtered, filtrate is collected, collects organic phase after being extracted with dichloromethane；
After the drying of 5g anhydrous sodium sulfate is added, by pillar layer separation, functionalization AIE molecule intermediate 4- (1,2,2- triphenyl is obtained
Vinyl) phenol；
(2) 4mmol functionalization AIE molecule intermediate is dissolved in 25mL methylene chloride, 12mmol triethylamine is added, and
8mmol acryloyl chloride is added dropwise, stirs 4h at room temperature, filters, vacuum distillation removes solvent, obtains functionalization AIE molecule 4-
(1,2,2- triphenyl vinyl) phenyl acrylate crude product；By pillar layer separation, pure functionalization AIE molecule is obtained.
Eluant, eluent used in pillar layer separation is the petroleum ether-ethyl acetate of volume ratio 1:30-1:10.
A method of rhodamine B being detected using aggregation-induced emission-molecular engram fluorescent optical sensor, by AIE- obtained
MIPs is added in testing sample solution, and room temperature on shaking table is placed on after mediation 1-5min and adsorbs 1-3h, is filtered, with 5-15mL dichloromethane
Alkane elution, is drained, fluorescence detection.
The condition of fluorescence detection: excitation wavelength is set as 345nm, and record transmitting range is 370-680nm.
The invention has the advantages that:
1, functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate prepared by the present invention belongs to four
Phenylethylene AIE molecule, it is good with fluorescence quantum yield height, structural stability, and synthesize simple, low in cost, easy modification
Outstanding advantages of.Since AIE molecule issues strong fluorescence in solid-state, AIE molecule is introduced into MIPs, fluorescence can be passed through
Spectrometer in situ detection rhodamine B.
2, binding molecule engram technology and detection technique of fluorescence of the present invention, use warfarin for template molecule, Alpha-Methyl third
Olefin(e) acid is function monomer, and ethylene glycol dimethacrylate is crosslinking agent, and azodiisobutyronitrile is initiator, and acetonitrile is solvent,
Functionalization AIE molecule is added, AIE-MIPs is synthesized using precipitation polymerization method.After AIE-MIPs and determinand are specifically bound,
Change in fluorescence can be directly generated in situ, by the variation of on-line checking fluorescence intensity, realize the detection to determinand.It is another
Aspect, since target analytes rhodamine B itself has color, it is difficult to which elution is clean completely, influences AIE-MIPs absorption front and back
The judgement of color change, therefore the present invention selects structure similar and does not have coloured warfarin as alternate template, using precipitating
Polymerization synthesizes AIE-MIPs.
3, AIE-MIPs of the present invention is not only easy to operate, less using organic reagent, and has specific adsorption ability, energy
Enough specific adsorption target molecules from complex system, the interference of despumation improve detection sensitivity and accuracy.Detection
AIE-MIPs adsorbs the fluorescence spectrum discovery after the rhodamine B solution of various concentration, and AIE-MIPs has rhodamine B stronger
Recognition capability, and linear relationship is good.It is 1 × 10 with AIE-MIPs difference adsorption concentration-5The rhodamine B of mol/L, brilliant blue,
Famille rose, amaranth, famille rose and the red solution of temptation, and its fluorescence spectrum is tested respectively, discovery AIE-MIPs is molten to rhodamine B
Liquid has excellent selectivity.And the AIE-MIPs after adsorbing can not have to elution, directly progress on-line checking.
4, fluorescent optical sensor AIE-MIPs of the invention, when detecting rhodamine B, with the increase of rhodamine B concentration, function
The fluorescence peak that AIE molecule can be changed gradually decreases, and the fluorescence peak of rhodamine B gradually rises, and changes in Ratio-type.AIE-MIPs is to sieve
After the standard curve of red bright B detection shows AIE-MIPs absorption rhodamine B solution, its fluorescence spectrum of on-line checking, in concentration model
Enclose is 1 × 10-5-10×10-5Linear relationship is good in mol/L.AIE-MIPs is used to the dry, Finda to actual sample pawpaw to drink
Material carries out recovery testu, the results showed that the rate of recovery range of rhodamine B is 96.2-103.5%, relative standard deviation range
For 1.5-4.7%.The AIE-MIPs that detection technique of fluorescence is combined with molecular imprinting technology, which is illustrated, in these tables of data to answer
Detection for rhodamine B in actual sample.
Detailed description of the invention
Fig. 1 is exciting light spectrogram (line a) and transmitted wave spectrogram (the line b) of functionalization AIE molecule.
Exciting light spectrogram (line a) and launching light spectrogram (the line b) that Fig. 2 is AIE-MIPs.
Fluorogram (a) of Fig. 3 functionalization AIE molecule in water/ethyl alcohol and uv absorption spectra (b).In figure, arrow
Indicate that the volume fraction of water increases direction.
Fig. 4 is fluorescence spectra of the functionalization AIE molecule in glycerine/ethyl alcohol.In figure, arrow indicates the body of glycerine
Fraction increases direction.
Fig. 5 is that AIE-MIPs adsorbs fluorescence spectra (a) and line style relational graph (b) after various concentration rhodamine B.
Fig. 6 is the fluorescence intensity ratio figure that AIE-MIPs and AIE-NIPs changes with rhodamine B concentration.
Fig. 7 is the fluorescence intensity ratio figure that AIE-MIPs adsorbs different pigments.
Fig. 8 is the standard curve that AIE-MIPs detects rhodamine B.
Specific embodiment
Specific embodiments of the present invention will be described in further detail with reference to embodiments.
The preparation of embodiment 1, functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate
(1) it weighs 2mmol triphen vinyl bromide to be put into 100mL round-bottomed flask, 2.4mmol 4- hydroxy benzenes boron is then added
Acid, 20mmol potassium carbonate provide alkaline environment, add 0.10mmol tetra- (triphenyl phosphorus) palladium, 15mL water and 25mL tetrahydrofuran
(THF) it is used as solvent, evacuate flask and is filled with nitrogen protection, reacts 12h under conditions of 85 DEG C；Products therefrom is filtered, is received
Collect filtrate, collects organic phase after being extracted with dichloromethane；After the drying of 5g anhydrous sodium sulfate is added, pass through pillar layer separation (elution
Agent be volume ratio 1:30-1:10 petroleum ether-ethyl acetate, gradient elution), obtain functionalization AIE molecule intermediate 4- (1,2,
2- triphenyl vinyl) phenol；
(2) 4mmol functionalization AIE molecule intermediate is dissolved in 25mL methylene chloride, 12mmol triethylamine is added, and
8mmol acryloyl chloride is added dropwise, stirs 4h at room temperature, filters, vacuum distillation removes solvent, obtains functionalization AIE molecule 4-
(1,2,2- triphenyl vinyl) phenyl acrylate crude product；By pillar layer separation, (eluant, eluent is volume ratio 1:30-1:10's
Petroleum ether-ethyl acetate, gradient elution), obtain pure functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenylpropen
Acid esters.
Products therefrom is characterized using high resolution mass spectrum, the cation peak that molecular weight is 403.1695 is obtained, with mesh
The molecular weight (403.1693) for marking molecule protonation is consistent, it was demonstrated that is 4- (1,2,2- triphenyl vinyl) phenyl acrylate.
Further, by elemental analysis, the constituent content obtained in product is C 86.59%, H 5.55%, O 7.86%, with theory
Value C86.54%, H 5.51%, O 7.95% matches.To functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl
Acrylate carries out spectrum analysis, the result is shown in Figure 1.As shown in Figure 1, the maximum excitation wavelength of functionalization AIE molecule is 365nm,
Best launch wavelength is 453nm.
The preparation of embodiment 2, aggregation-induced emission-molecular engram fluorescent optical sensor (AIE-MIPs)
It accurately weighs warfarin 1.0mmol to be placed in 250mL there-necked flask, be added 0.2g azodiisobutyronitrile (AIBN),
Then 9mmol α-methacrylic acid (α-MAA) is added in 150mL acetonitrile, 60mmol ethylene glycol dimethacrylate (EDMA),
Add 0.01mmol functionalization AIE molecule 4- (1,2,2- triphenyl vinyl) phenyl acrylate (the 1/ of template mole
100), ultrasonic vibration 15min dissolves it all, and under conditions of 83 DEG C, mechanic whirl-nett reaction 8h is filtered, and dries, elution,
Obtain AIE-MIPs.
Wherein, the method for elution are as follows: build soxhlet type apparatus, the mixed of 200mL methanol and acetic acid (volume ratio 4:1) is added
Liquid is closed, synthetic AIE-MIPs is wrapped with filter paper and is put into Soxhlet extraction device, after 90 DEG C of temperature control, elution 3 days, is used
The pure methanol elution of 150mL, at regular intervals with the fluorescence spectrum of fluorescence detector measurement eluent, the fluorescence of warfarin molecule
Launch wavelength is 385nm, then illustrates that elution is clean without peak at this wavelength, is finally dried for standby.
Fig. 2 is the fluorescence excitation and emission spectra figure of AIE-MIPs, as shown in Figure 2, the maximum excitation wavelength of AIE-MIPs
It is 345nm, best launch wavelength is 450nm.
The test of embodiment 3, functionalization AIE molecule performance
Influence of 3.1 solvents to functionalization AIE molecular fluorescence intensity
Respectively with water/ethyl alcohol mixed solvent (volume fraction of water is respectively 0%, 10%, 20%, 30%, 40%,
50%, 60%, 70%, 80%, 90%, 100%) compound concentration be 1 × 10-5Mol/L functionalization AIE molecular solution, spare, inspection
Fluorescence spectrum is surveyed, as a result sees Fig. 3 (a).By Fig. 3 (a) it is found that fluorescent emission obviously increases when the volume fraction of water reaches 70%
By force.Fluorescence intensity ratio fluorescence intensity in straight alcohol of the functionalization AIE molecule in pure water is 45 times high.Under normal circumstances, water
It is the poor solvent of most of organic matters, functionalization AIE molecule is assembled in water, therefore generates strong fluorescence, i.e. AIE
It shines.Therefore, with the increase of the volume fraction of in the mixed solvent water, functionalization AIE molecule is gradually assembled, and functionalization AIE points
The fluorescence of son gradually increases.
It is the aggregation because of functionalization AIE molecule to further verify the fluorescence in water/ethyl alcohol, has detected UV absorption
Spectrum, as shown in Fig. 3 (b).In alcohol solvent, functionalization AIE molecule has good dissolubility, and occurs at 312nm
One absorption peak.However, aggregation can be generated in the solution since the solubility of functionalization AIE molecule in water is lower,
To which light scattering phenomenon occur.The fine structure of corresponding ultra-violet absorption spectrum disappears and in the visual field 260-500nm of spectrum
It being capable of ultraviolet trailing phenomenon visible in detail, it was demonstrated that functionalization AIE molecule is in coherent condition in water.
Influence of 3.2 solvent viscosities to luminescent properties
Respectively with glycerine/ethyl alcohol mixed solvent (volume fraction of glycerine be 0%, 10%, 20%, 30%,
40%, 50%, 60%, 70%, 80%, 90%, 100%) compound concentration be 1 × 10-5Mol/L functionalization AIE molecular solution, it is standby
With as a result detection fluorescence spectrum is shown in Fig. 4.As shown in Figure 4, the luminescent properties of functionalization AIE molecule are influenced by solvent viscosity.
In glycerine/alcohol solvent of different proportion, as the volume fraction of glycerine increases, the fluorescence of functionalization AIE molecule is strong
Degree gradually increases.This is because solvent viscosity increases, the Internal Rotations of Molecules of functionalization AIE molecule is limited, so that functionalization AIE
Molecule issues very strong fluorescence.
Embodiment 4, AIE-MIPs Static Adsorption curve measurement
Various concentration gradient (0,1 × 10 is prepared with distilled water-6、5×10-6、1×10-5、5×10-5、1×10-4、5×10-4Mol/L rhodamine B solution), accurately weigh 6 parts of AIE-MIPs and 6 part of AIE-NIPs (the same AIE-MIPs of preparation method, uniquely
Difference is to be added without warfarin) 60mg is individually placed in 10mL centrifuge tube, each rhodamine B that the above-mentioned various concentration of 5mL is added
Solution, after mediation 1min under be placed on room temperature on shaking table and adsorb 1h, filter, with 5mL eluent methylene chloride, drain, obtain adsorbing not
With AIE-MIPs the and AIE-NIPs solid of concentration rhodamine B, for fluorescence spectrum detection (Fig. 5,6).
By Fig. 5 (a) it is found that after the rhodamine B solution of AIE-MIPs absorption various concentration, fluorescence peak at 450nm by
It gradually reduces, fluorescence peak gradually rises at 582nm, changes in Ratio-type.By Fig. 5 (b) it is found that being 1 × 10 in rhodamine B concentration-6-
1×10-4In the range of mol/L, the 582nm and fluorescence intensity ratio (I at 450nm wavelength582/I450) and rhodamine B solution
With good linear relationship, linear equation y=0.00606+0.02475x, wherein R2=0.9992.
It will be appreciated from fig. 6 that when the rhodamine B of absorption various concentration, I corresponding to AIE-MIPs582/I450Always compare AIE-
I corresponding to NIPs582/I450Greatly.This illustrates that the adsorption capacity of the adsorption capacity ratio AIE-NIPs of AIE-MIPs is strong.
The adsorption selectivity test of embodiment 5, AIE-MIPs
1 × 10 is prepared respectively-5The temptation of mol/L is red, carmine, amaranth, magenta, brilliant blue, rhodamine B solution, accurately
It weighs 6 parts of AIE-MIPs 60mg to be respectively put into 10mL centrifuge tube, each different material solution that the above-mentioned same concentrations of 5mL are added,
It is placed on room temperature on shaking table after mediation 1min and adsorbs 1h, filters, with 5mL eluent methylene chloride, drains, obtains absorption different material
AIE-MIPs solid.AIE-MIPs after absorption is used for fluorescence spectrum detection (Fig. 7).As shown in Figure 7, AIE-MIPs adsorbs sieve
Corresponding I after red bright B solution582/I450Much larger than other pigments.This illustrates that AIE-MIPs has choosing very well to rhodamine B
The absorption of selecting property and detectability.
Embodiment 6, actual sample analysis
The drafting of 6.1 standard curves
Prepare various concentration gradient (1 × 10-5、2×10-5、3×10-5、4×10-5、5×10-5、6×10-5、7×10-5、8
×10-5、9×10-5、10×10-5Mol/L rhodamine B solution) accurately weighs 10 parts of AIE-MIPs 60mg and is respectively put into
In 10mL centrifuge tube, the solution of the above-mentioned various concentration of 5mL is respectively added, room temperature on shaking table is placed on after mediation 1min and adsorbs 1h, is filtered,
It with 5mL eluent methylene chloride, drains, obtains the AIE-MIPs solid of absorption rhodamine B, every a solid is subjected to fluorescence spectrum
Detection.Above-mentioned experiment does three groups in parallel, as a result sees Fig. 8.
As shown in Figure 8,1 × 10-5-10×10-5Within the scope of mol/L, AIE-MIPs has rhodamine B solution good
Linearity test ability, linear equation are as follows: y=0.44247+0.24773x, R2=0.99698.
The processing of 6.2 actual samples
The processing of pawpaw dry-eye disease: it accurately weighs 30.00g and grinds that uniform pawpaw is dry to be placed in 250mL conical flask, be added
90mL Tris buffer solution (pH=7.5), concussion mixes 10min on shaking table, and ultrasonic extraction 10min is transferred to centrifuge tube
In, 10min is centrifuged at 4000rpm with extraction fluid and the dry precipitating of pawpaw, it is dry heavy that repetition above step extracts pawpaw repeatedly
It forms sediment three times, merges supernatant, be settled to 300mL with Tris buffer solution, reuse Buchner funnel, bottle,suction adds 0.45 μm of filter membrane
Filtering, filtrate is stored in spare in conical flask.
The processing of Finda beverage: accurately weighing 30.00g beverage, and heating boils 5min to remove CO in beverage on electric furnace2And
Other volatile impurity are settled to 300mL with Tris buffer solution, add 0.45 μm of membrane filtration using Buchner funnel, bottle,suction,
It is stored in spare in conical flask.
The application of 6.3AIE-MIPs rhodamine B in detection actual sample
60mg AIE-MIPs is accurately weighed in 10mL centrifuge tube, testing sample solution 5mL is added, is put after mediation 1min
Room temperature adsorbs 1h on shaking table, filters, with 5mL eluent methylene chloride, drains, and collects filter cake, is measured and is sent out using Fluorescence Spectrometer
Penetrate spectrogram.It is parallel to carry out three groups, and repetition above step carries out 3.0 × 10 using actual sample as matrix respectively-5、6.0×
10-5、9.0×10-5The mark-on of mol/L rhodamine B solution is tested, and the results are shown in Table 1.
The recovery of standard addition of 1 actual sample of table
As shown in Table 1, recovery of standard addition the range 101.7-103.5%, relative standard deviation (Relative of Finda beverage
Standard Deviation, abbreviation RSD) range be 2.2-3.5%；The dry recovery of standard addition range 96.2- of pawpaw
The range of 98.7%, RSD are 1.5-4.7%.Thus it can illustrate that the recovering effect of this method is good, can be used for rhodamine in food
The analysis detection of B.
The foregoing is merely preferred embodiments of the present invention, and for those skilled in the art, the present invention can have
Various modifications and variations.All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on, should all
It is included within protection scope of the present invention.
Claims (10)
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| CN114106245A (en) * | 2021-12-14 | 2022-03-01 | 嘉兴学院 | AIE-based fluorescent molecularly imprinted polyionic liquid and its preparation method and application |
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