CN107629161A - A kind of 2,4,6 trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers and its application - Google Patents
A kind of 2,4,6 trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers and its application Download PDFInfo
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Abstract
The present invention discloses one kind 2, 4, 6 trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers and its application, it is with the 2 of precipitation polymerization method synthesis, 4, 6 trichlorophenol, 2,4,6,-Ts are template molecule, 7 allyloxy cumarins are as function monomer, ethylene glycol two (methacrylic acid) ester (EGDMA) is crosslinking agent, 2, 2' azodiisobutyronitriles (AIBN) are initiator, and template molecule and function monomer are dissolved in acetonitrile, sonic oscillation, prepolymerization is stood at room temperature, add crosslinking agent, it is eventually adding initiator, by the mixed liquor sonic oscillation, lead to nitrogen after degassing, using thermal-initiated polymerization mode, it is placed in thermostatical oil bath and heats, gained white precipitate polymer after polymerization；Again with containing acetic acid methanol solution elute, after soaked repeatedly with methanol solution, be dried in vacuo and produce.The polymer light-emitting is uniform, stability is good, has high sensitivity and relatively low detection limit, and has stronger Selective recognition ability to trichlorophenol, 2,4,6,-T, can be applied to the quantitative detecting analysis of the trichlorophenol, 2,4,6,-T of ultra trace 2,4,6.
Description
Technical field
It is suitable more particularly to one kind the present invention relates to the fluorescence molecule imprinted polymer in environment functional material preparation field
The trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymer detected for Selective recognition and using fluorescence, the invention further relates to environment
The application of the context of detection of the polymer parachlorphenol class compound is utilized in analysis.
Background technology
Molecular imprinting technology（Molecular imprinting technology, MIT）Molecular imprinting technology refers to obtain
Obtain the experiment technology of preparing of the polymer matched completely with a certain molecule (template molecule) on space structure and binding site, system
Standby polymer is referred to as molecularly imprinted polymer（Molecularly imprinted polymers, MIPs）.Molecule prints at present
Mark polymer is widely used with its excellent performance in the field such as biology, chemistry, medical science.In recent years, have many
Fluorescent dye is incorporated into molecular imprinting technology by research work, prepares Multifunction fluorescent molecular engram material.Therefore, will have
The photoluminescent property of machine fluorometric reagent and the selective binding of molecular imprinting technology, the fluorescence molecule imprinted material prepared is in complexity
Obvious advantage and more superior optical property will be had in the separation detection of sample.
Phenols endocrine disruptors（Phenolic Endocrine Disruptors, PEDs）It is environment incretion interference
Typical organic environment hormone in thing.Pass through the production process of the mankind（Such as coking, oil refining, manufacture coal gas, phenol, insulating materials,
Medicine, papermaking etc.）Waste water, the waste gas of middle exclusion are discharged into environment, influence to swash in human body and animal body by bioconcentration
Synthesis, secretion, effect and metabolism of element etc..PEDs mainly includes chlorophenol, alkyl phenol and bis-phenol etc..Wherein, chlorophenol has chemistry
Structure is more more stable than alkyl phenol and bis-phenol, and decomposition or biodegradation are not likely to produce under natural conditions, causes to continue and long
The harm of phase.And chlorophenol is easily entered in human body and organism by the bioconcentration of food chain, serious threat life
State balances and the health of the mankind.In addition, the nuclear substituted chlorine atom of chlorinated phenols benzene has very strong toxicity to microorganism, this
And chlorophenol it is biodegradable difficult the reason for one of.2,4,6- trichlorophenol, 2,4,6,-Ts（That is 2,4,6-TCP）, 2,4 dichloro phenol（2,4-
DCP）129 kinds of preferential organic pollutions for administering control have been included in by USA and EU tissue Deng 25 kinds of chlorinated phenols,
It is that Chinese Government is classified as the toxic organicses that must be controlled first.In recent years, with bactericide, preservative, defoliant, have
The fast development of the industries such as machine synthesis, papermaking, printing and dyeing, increasing chlorophenol pollutants are discharged into environment with waste water, waste gas
Harm biology and the mankind.At present, researcher is in environment and Exposed person serum, environmental water sample, food and river
The presence of chlorophenol is detected in stream bed mud.As can be seen here, the detection for chlorophenols compound has turned into very urgent and worked as
Business is anxious.Now conventional chlorophenols compound detection method has AAS, gas chromatography, high performance liquid chromatography, stream
Dynamic injection-chemoluminescence method, electrochemical process, capillary electrophoresis etc..The detection limit of methods described, the range of linearity and advantage and disadvantage are each
Differ, for complicated component, structure in environment be similar, the detection of trace/ultra trace environment incretion interferent residual, also deposit
Recognition efficiency is low, poor selectivity, the field that sensitivity is low, signal is weak thirst for solving but still unsolved technology all the time
Problem.
The content of the invention
It is an object of the invention to provide a kind of 2,4,6- trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers and its application, its institute
The fluorescence molecule imprinted polymer being related to（Fluorescent Molecularly imprinted polymers, F-MIPs）,
Particle size distribution range is narrow, and synthesis is simple, and selectivity is high, and is combined with detection technique of fluorescence, this method is not only had selection
The outstanding features such as property is strong, sensitivity is high, detection limit is low, speed is fast, signal is strong, and it is completely suitable for Environmental Trace/super trace
Measure the detection of trichlorophenol, 2,4,6,-T.Make the field thirst for solving but still unsolved technical barrier all the time to be resolved.
The fluorescence molecule imprinted polymer of the present invention is using the 2,4,6- trichlorophenol, 2,4,6,-Ts of precipitation polymerization method synthesis as template point
Son, AP20am12 is function monomer or fluorescent dye, ethylene glycol two (methacrylic acid) ester (EGDMA) are crosslinking
Agent, 2,2'- azodiisobutyronitriles (AIBN) are initiator, and are produced by following step：By template molecule 2,4,6- trichlorophenol, 2,4,6,-Ts
It is dissolved in function monomer AP20am12 in appropriate acetonitrile, sonic oscillation, stands prepolymerization 12h at room temperature, make function
Monomer and 2,4,6- trichlorophenol, 2,4,6,-Ts fully act on, and add the crosslinking agent EGDMA of the amount of 2-2.5 times of function monomer material, finally
Initiator A IBN is added, its addition is the 2.5% of the amount of monomer total material, by the above-mentioned min of mixed liquor sonic oscillation 3 ~ 4
Lead to the min of nitrogen 10 after degassing, seal under nitrogen atmosphere；Using thermal-initiated polymerization mode, 60 DEG C of constant temperature oil baths are placed on
24 h are heated in pot, after the completion of polymerization, obtain white precipitate polymer；It is eluted with the methanol solution containing acetic acid (V/V) 10%,
Remove template molecule, after with methanol solution soak sediment repeatedly, to wash away the acetic acid of residual, vacuum drying, produce fluorescence point
Sub- imprinted polymer F-MIPs.
The preparation of the function monomer is by 10 mmol umbelliferone, 12 mmol allyl bromide, bromoallylenes and trace
Iodine is dissolved in 100ml DMF, then 10 mmol potassium carbonate are added into solution.The min of mixed liquor sonic oscillation 3 ~ 4 is taken off
Lead to the min of nitrogen 10 after gas, under nitrogen atmosphere, be placed in 70 DEG C of thermostatical oil baths and heat 24 h.Product is recrystallized
Obtain AP20am12.
The consumption proportion of described trichlorophenol, 2,4,6,-T, function monomer and acetonitrile is 2：2：(30-60)mmol/ mmol/mL
The fluorescence molecule imprinted polymer of the present invention is applied to 2,4, the 6-TCP fluorogenic quantitative detection to residual, it is operated
Method is accurately prepare 11 kinds of concentration first 2,4,6-TCP graded alcohols solution, then weighs 50 mg F-MIPs loadings 10
In ml centrifuge tubes, 2 prepared are measured respectively, each 5 ml of 4,6-TCP solution, 10 ml is poured into and is equipped with F-MIPs, ultrasonic disperse
Afterwards, 8h, centrifuging and taking solid, drying are stood.Using sepectrophotofluorometer fluorescence intensity, describe fluorescence intensity-concentration mark
Directrix curve.Fluoroscopic examination to F-NIPs trichlorophenol, 2,4,6,-Ts is carried out in the same way.
Advantages of the present invention and good effect：The narrow fluorescence molecule trace of particle size distribution range is prepared using precipitation polymerization method
Polymer microballoon, using the umbelliferone of pi-allyl modification as function monomer or fluorescent dye, copolymerzation with cross-linking, make 7-
Allyloxy cumarin, which is evenly dispersed in polymer, forms the hole with recognition reaction, obtains fluorescence imprinted polymer hair
Light is uniform and luminosity is excellent, and stability is good, repeated strong, is applied to 2,4,6-TCP fluorogenic quantitative detection, has
High sensitivity and relatively low detection limit, and there is stronger Selective recognition ability to trichlorophenol, 2,4,6,-T, it is reliable to realize to detection
In the range of 2,4,6-TCP concentration quantitative detecting analysis.Compared with prior art with prominent substantive distinguishing features and significantly
Progress.
Brief description of the drawings
Fig. 1 is AP20am12 nuclear magnetic spectrogram；AP20am121H NMR (400 MHz, CDCl3)
δ 7.63 (d, J = 9.5 Hz, 1H), 7.37 (d, J = 8.6 Hz, 1H), 6.89 – 6.79 (m, 2H),
6.25 (t, J = 6.7 Hz, 1H), 6.04 (ddd, J = 17.2, 10.6, 5.3 Hz, 1H), 5.49 – 5.28
(m, 2H), 4.60 (d, J= 5.3 Hz, 2H)（Under）Prove that AP20am12 synthesizes successfully.
Fig. 2 is umbelliferone (a), AP20am12 (b) and F-MIP (c) infrared spectrograms；Fig. 2 (a)
In 3443 be hydroxyl stretching vibration peak diminish, (b) 3080cm-1,3055cm-1,3022cm-1 corresponds to the C- of pi-allyl respectively
H stretching vibration peaks, illustrate successfully to synthesize the success of allyloxy cumarin.1730cm in Fig. 2 (c)-1、1258cm-1、1151cm-1
C=O stretching vibration peak in EGDMA, C-O antisymmetry and symmetrical stretching vibration peak are corresponded to respectively；2986th, 2956 be 7- hydroxyls
H stretching vibration illustrates polymer successful polymerization under initiator A IBN initiations on butylcoumariii phenyl ring.
Fig. 3 is the ESEM (SEM) of F-MIPs microballoons.It is seen that the pattern of polymer gradually levels off to rule
It is then spherical, and surface convergence is smooth；The diameter of microballoon is about 2 μm, and particle diameter distribution is more uniform.
Fig. 4 is umbelliferone（a）, AP20am12（b）With F-MIPs microballoons（c）Fluorescence spectrum；From
Either AP20am12 is can be seen that in figure（b）Fluorescent emission compared with umbelliferone（a）8nm blue shift is produced,
F-MIPs microballoons（c）Compared with AP20am12（b）20nm blue shift is produced, and all there is excellent fluorescent emission.
Fig. 5, Fig. 6 are the response curve of F-MIPs, F-NIPs microballoon and trichlorophenol, 2,4,6,-T respectively；F-MIPs fluorescence intensity with
The linear reducing tendency of increase of template molecule concentration, and F-NIPs fluorescence intensity and the change in concentration of template molecule are without obvious
Quenching phenomenon.
Fig. 7 is disturbance thing solution that concentration is 20 nM to F-MIPs, F-NIPs quenching effect figure；Can from figure
With find out the similar chaff interference of structure to template molecule without effect is significantly interfered with, and template molecule has stronger be quenched to F-MIP
Effect.Prove that F-MIPs has very strong recognition reaction to template molecule.
Fig. 8 is that concentration is the quenching effect figure of 20 nM chaff interference and the mixed solution of template molecule to F-MIPs.From
The similar chaff interference of it can be seen from the figure that structure to template molecule without significantly interfere with effect, and template molecule have to F-MIPs it is stronger
Quenching effect.Prove that F-MIPs has stronger antijamming capability.
Embodiment
The fluorescence molecule imprinted polymer of the present invention is prepared, is to prepare function monomer first.The preparation of the function monomer：
It is in the 100ml DMF for being dissolved in the iodine of 10 mmol umbelliferone, 12 mmol allyl bromide, bromoallylenes and trace, then to molten
10 mmol potassium carbonate are added in liquid.Lead to the min of nitrogen 10 after the min of mixed liquor sonic oscillation 3 ~ 4 is deaerated, in nitrogen
Under atmosphere, it is placed in 70 DEG C of thermostatical oil baths and heats 24 h.Product is recrystallized, obtains AP20am12.
It is the preparation of fluorescence molecule imprinted polymer below：
Embodiment 1 takes the mmol of template molecule 2,4,6-TCP 2, the mmol of function monomer AP20am12 2 to be dissolved in 30mL
Acetonitrile（The mass fraction of monomer is less than 5%）In, sonic oscillation, prepolymerization 12h, makes function monomer and 2,4,6-TCP at room temperature
Phenol fully acts on, and crosslinking agent EDMA 1.88 mL, initiator A IBN 0.1g is added, by above-mentioned mixed liquor sonic oscillation 3 ~ 4
Min is deaerated, and the logical min of nitrogen 10 emptyings, are sealed under nitrogen atmosphere afterwards.Using thermal-initiated polymerization mode, 60 are placed on
24 h are heated in DEG C thermostatical oil bath, after the completion of polymerization, obtain white precipitate polymer.It is used to the methanol of acetic acid (V/V) 10%
Solution elutes, and removes template molecule, after with methanol solution soak sediment repeatedly, to wash away the acetic acid of residual, vacuum drying.I.e.
Obtain F-MIPs.The non-imprinted polymer of fluorescence molecule (Fluorescent Molecularly non-imprinted polymers,
F-NIPs preparation) except be not added with template molecule and without soxhlet extraction in addition to method it is identical with F-MIPs.
Embodiment 2 takes the mmol of template molecule 2,4,6-TCP 2, the mmol of function monomer AP20am12 2 to be dissolved in
In 60mL acetonitriles, sonic oscillation, prepolymerization 12h, makes function monomer and 2 at room temperature, and 4,6-TCP fully act on, and adds crosslinking
Agent EDMA1.6 mL, initiator A IBN60 mg, the above-mentioned min of mixed liquor sonic oscillation 3 ~ 4 is deaerated, afterwards logical nitrogen 10
Min is emptied, and is sealed under nitrogen atmosphere.Using thermal-initiated polymerization mode, it is placed in 60 DEG C of thermostatical oil baths and heats 24
H, after the completion of polymerization, obtain white precipitate polymer.It is eluted with the methanol solution of acetic acid (V/V) 10%, removes template molecule,
Sediment is soaked repeatedly with methanol solution afterwards, to wash away the acetic acid of residual, vacuum drying.Obtain F-MIPs.And prepared by F-NIPs
Method is same as above in addition to being not added with template molecule and carrying out soxhlet extraction.
The fluorescence molecule imprinted polymer of the invention described above is applied to the inspection to the 2,4,6- trichlorophenol, 2,4,6,-T concentration of residual
Survey, carry out in the steps below：2,4,6-TCP graded alcohols solution of 11 kinds of concentration are accurately prepared first, weigh 50 mg F-
MIPs loads 10ml centrifuge tubes, measures 11 kind 2 prepared respectively, each 5 ml of 4,6-TCP solution, pours into centrifugation tube-in-tube,
Ultrasonic disperse, stand 8h.Utilize sepectrophotofluorometer fluorescence intensity.According to Stern-Volmer equations:
(I 0 /I)-1 = K SV·[C]
With concentration [C] for abscissa, relative intensity of fluorescence (I 0 /I)-1Fluorescence response curve is drawn for ordinate.At the same time,
Several structures and kin phenol compound are selected, as competition detectable substance, the selectivity for participating in research F-MIPs is known
Other performance.
Embodiment 3 accurately prepares 11 kinds of concentration（0、1、2、5、10 、20、50、100、200、500、1000nM）2,4,
6-TCP graded alcohols solution, 11 kind 2 prepared is measured respectively, each 5 ml of 4,6-TCP solution, which is moved into, weighs 50 mg fluorescence print
In the 10ml of mark polymer centrifuge tube, ultrasound, 8h is stood, centrifuging and taking solid, is dried.Detected using sepectrophotofluorometer glimmering
Luminous intensity, fluorescence intensity-concentration standard curve is described according to Stern-Volmer equations.
Embodiment 4 selects the phenol that 2,4- chlorophenesic acids, 2,5- chlorophenesic acids, 2,6- chlorophenesic acids identify for competition
Compound.Three of the above phenol and 2 is prepared, the alcohol mixed solution of 4,6- trichlorophenol, 2,4,6,-Ts, concentration is 20 nM.Weigh 50mg's
Fluorescent polymer pours into centrifuge tube, measures each 5 ml of 4 kinds of phenol solutions prepared respectively, moves into 10 ml centrifuge tubes, surpasses
Sound, 8h is stood, centrifugation leaves solid, dries.Utilize sepectrophotofluorometer fluorescence intensity, detection selectivity.
Embodiment 5 selects the phenol that 2,4- chlorophenesic acids, 2,5- chlorophenesic acids, 2,6- chlorophenesic acids identify for competition
Compound.Three of the above phenol and 2 is prepared, the alcohol mixed solution of 4,6- trichlorophenol, 2,4,6,-Ts, concentration is 20 nM.Weigh 50mg's
Fluorescent polymer pours into centrifuge tube, measures the ml of phenol mixed solution 5 prepared, moves into 10 ml centrifuge tubes, ultrasound, stands
8h, centrifugation leave solid, dry.Using sepectrophotofluorometer fluorescence intensity, anti-interference is detected.
The embodiment can further demonstrate that：The fluorescence molecule imprinted polymer prepared by the present invention not only has luminous equal
Uniform quite excellent photoluminescent property, and be applied to 2,4,6-TCP fluorogenic quantitative detection, have high sensitivity and
Relatively low detection limit, there is stronger Selective recognition ability to trichlorophenol, 2,4,6,-T, can reliably realize to 2 in detection range, 4,
The quantitative detecting analysis of 6-TCP concentration.With vast potential for future development.
Claims (5)
1. one kind 2,4,6- trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers, it is characterised in that：It with precipitation polymerization method synthesis 2,
4,6- trichlorophenol, 2,4,6,-Ts are template molecule, and AP20am12 is as function monomer or the fluorescent dye, (methyl-prop of ethylene glycol two
Olefin(e) acid) ester (EGDMA) is crosslinking agent, 2,2'- azodiisobutyronitriles (AIBN) are initiator, and are produced by following step：By mould
The trichlorophenol, 2,4,6,-T of plate molecule 2,4,6- and function monomer AP20am12 are dissolved in appropriate acetonitrile, sonic oscillation, at room temperature
Prepolymerization 12h is stood, makes function monomer and 2,4,6- trichlorophenol, 2,4,6,-Ts fully act on, 2-2.5 times of function monomer material of addition
The crosslinking agent EGDMA of amount, is eventually adding initiator A IBN, and its addition is the 2.5% of the amount of monomer total material, will be described mixed
Lead to the min of nitrogen 10 after closing the min degassings of liquid sonic oscillation 3 ~ 4, seal under nitrogen atmosphere；Using thermal-initiated polymerization mode,
It is placed in 60 DEG C of thermostatical oil baths and heats 24 h, after the completion of polymerization, obtains white precipitate polymer；It is used and contains acetic acid
(V/V) 10% methanol solution elution, removes template molecule, after with methanol solution soak sediment repeatedly, to wash away the second of residual
Acid, vacuum drying, produces fluorescence molecule imprinted polymer F-MIPs.
2. according to claim 12,4,6- trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers, it is characterised in that：The function
The preparation of monomer AP20am12 is by 10 mmol umbelliferone, 12 mmol allyl bromide, bromoallylenes and trace
Iodine is dissolved in 100ml DMF, then 10 mmol potassium carbonate are added into solution, and the min of mixed liquor sonic oscillation 3 ~ 4 is taken off
Lead to the min of nitrogen 10 after gas, under nitrogen atmosphere, be placed in 70 DEG C of thermostatical oil baths and heat 24 h.Product is tied again
Crystalline substance.
3. according to claim 12,4,6- trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers, it is characterised in that：Described 2,
4,6- trichlorophenol, 2,4,6,-Ts, AP20am12, the consumption proportion of acetonitrile are 2：2：(30-60)mmol/ mmol/mL.
4. according to claim 12,4,6- trichlorophenol, 2,4,6,-T fluorescence molecule imprinted polymers, it is characterised in that：The polymerization
Thing is applied to 2,4, the 6-TCP fluorogenic quantitative detection to residual, and its operating method is accurately prepare 11 kinds of concentration first 2,
4,6-TCP graded alcohols solution, the F-MIPs for then weighing 50 mg are fitted into 10 ml centrifuge tubes, measure 2 prepared respectively,
Each 5 ml of 4,6-TCP graded alcohols solution, pour into centrifuge tubes of 10 ml equipped with F-MIP, after ultrasonic disperse, stand 8h, centrifugation
Solid is taken, is dried, recycles sepectrophotofluorometer fluorescence intensity, describes fluorescence intensity-concentration standard curve, and F-
Fluoroscopic examinations of the NIPs to 2,4,6- trichlorophenol, 2,4,6,-Ts is carried out in the same way.
5. the fluorogenic quantitative detection to the 2 of residual, 4,6-TCP according to claim 4, it is characterised in that：Described 11 kind 2,
4,6-TCP graded alcohols solution concentration is 0 respectively, 1,2,5,10,20,50,100,200,500,1000nM.
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