CN107353369A - A kind of photonic crystal sensor material and its preparation method and application - Google Patents
A kind of photonic crystal sensor material and its preparation method and application Download PDFInfo
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- CN107353369A CN107353369A CN201710557860.9A CN201710557860A CN107353369A CN 107353369 A CN107353369 A CN 107353369A CN 201710557860 A CN201710557860 A CN 201710557860A CN 107353369 A CN107353369 A CN 107353369A
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- 0 CC(C)(C*(*)c(cc1)cc(O)c1O)*C(*)=C Chemical compound CC(C)(C*(*)c(cc1)cc(O)c1O)*C(*)=C 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Oc(cccc1)c1O Chemical compound Oc(cccc1)c1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/06—Oxidation
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- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/47—Scattering, i.e. diffuse reflection
- G01N21/4788—Diffraction
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- Plural Heterocyclic Compounds (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention discloses a kind of photonic crystal sensor material and its preparation method and application, the preparation method includes：(1) in the presence of an inert gas, compound shown in compound shown in formula I, formula II, water and initiator are contacted, carries out emulsifier-free emulsion polymerization reaction, obtain polymer microballoon；(2) by the polymer microballoon and H2O2With HRP haptoreactions, PMD microballoons are obtained；(3) disperse by the suspension of the PMD microballoons and stand heap to build, the photonic crystal sensor material is made；The photonic crystal sensor material preparation process of the present invention is simple, and during for detecting, detection is easy to operate, and response is rapid, high sensitivity, and detection range is wide；Wherein, R is the group containing alkylene, alkynes base, olefin amide base or alkene ester group.
Description
Technical field
The present invention relates to field of food safety, more particularly, to a kind of photonic crystal sensor material and preparation method thereof
And application.
Background technology
Ciprofloxacin [fluoro- 1,4- dihydros -4- oxos -7- (piperazinyl) quinolone -3- carboxylic acids of 1- cyclopropyl -6-]
(Ciprofloxacin, CF) belongs to FQNS, and it is the synthetic antibiotic with broad-spectrum antimicrobial effect, and it is sterilized
Effect is good and cheap, therefore as one of the most frequently used antibiotic of fish culture.But CF a large amount of uses, it can be caused in ring
A large amount of residuals in border and relevant food, particularly in fish culture waters and the flesh of fish, these can not only promote bacterial drug resistance
Generation, CF is entered human body by food chain, endanger people's health.Therefore, there is an urgent need to monitor CF residual,
With guarantee environment and food security.
So far, there are many methods to monitor the CF contents in cultivation fish and water, including high performance liquid chromatography
(HPLC), fluorescence spectrum, enzyme linked immunosorbent assay (ELISA) (ELISA), micro-biological process, Capillary Electrophoresis and various spectrophotometrics
Method.But these methods need professional to operate, and need the pretreatment of complicated and time consumption.
Photonic crystal (PC), exactly the dielectric material of differing dielectric constant is entered in space according to certain cycle sequences
The orderly periodic structure material with optical wavelength magnitude is formed after row arrangement.When light is propagated in the photonic crystal, it may occur that cloth
Glug diffraction, diffraction wavelength follow following law：M λ=2ndsin θ, exactly this diffraction make photonic crystal have unique knot
Structure color.If the lattice parameter of photonic crystal changes, the change of diffraction wavelength can be caused, therefore, photonic crystal is as one
Kind sensing material, it is possible to achieve without reagent, unmarked quick detection.
Holtz et al. is prepared for a kind of photonic crystal that response can be produced to metal ion.First, the bases such as crown ether will be carried
The latex particle that the single dispersing of group is powered is dispersed in the monomer solution of acrylic amide, forms the composite junction of high-sequential
Structure, initiation polymerization is then carried out, finally give the colloid array of ordered structure.Crown ether functional group selectivity in colloid array
Chelated with metal ion, raise colloid array osmotic pressure, volume sweell(ing), spacing of lattice increase, finally cause Prague
Diffraction maximum red shift.The suction-operated is reversible, the colloid array of swollen state is immersed in deionized water, colloid array
Internal penetration pressure can reduce again, and Bragg diffraction peak is returned to home position again.Phenyl boric acid group is introduced photon by Asher et al.
In crystal array, the detection for glucose.The photon crystal material can respond to various saccharides under low ionic strength.
In addition, also develop can be to Na by researcher+、K+、Pb2+, pH value, temperature, illumination, the photon of the generation such as mechanical force response it is brilliant
Body.
At present, there has been no the photonic crystal of detection Ciprofloxacin, also, above-mentioned these photon crystal materials preparation technology answers
It is miscellaneous, it is necessary to prepare microballoon and be dispersed in gel and be fixed；Some then needs first to prepare opal template, then in mould
Polymer is poured into plate stitch gap, then etches away opal template.
Therefore, it is necessary to a kind of preparation method for the photonic crystal sensor material for detecting Ciprofloxacin is provided, meanwhile, overcome
Photon crystal material preparation technology is complicated at present, prepares the problems such as cost height.
The content of the invention
It is an object of the invention to provide a kind of photonic crystal sensor material and its preparation method and application, the photonic crystal passes
Sense material can detect Ciprofloxacin, and preparation technology is simple, it is low to prepare cost.
To achieve these goals, the first aspect of the present invention provides a kind of preparation side of photonic crystal sensor material
Method, the preparation method include：
(1) in the presence of an inert gas, compound shown in compound shown in Formulas I, Formula II, water and initiator are contacted, entered
Row emulsifier-free emulsion polymerization reacts, and obtains polymer microballoon；
Wherein, R is the group containing alkylene, alkynes base, olefin amide base or alkene ester group；
(2) by the polymer microballoon and H2O2With HRP haptoreactions, PMD microballoons are obtained；
(3) disperse by the suspension of the PMD microballoons and stand heap to build, the photonic crystal sensor material is made.
The second aspect of the present invention provides photonic crystal sensor material made from a kind of described preparation method.
The third aspect of the present invention is described photonic crystal sensor material as dinitrogen heterocyclic compound detection reagent
Using, wherein, the dinitrogen heterocyclic compound is the compound with group shown in formula IV,
Technical scheme has the following advantages that：
(1) photonic crystal sensor material preparation process of the invention is simple, it is only necessary to by prepare microballoon by oxidation and heap
Base can obtain photonic crystal sensor material；
(2) condition of heap of the invention base photonic crystal is simpler, and the heap of microballoon is built can be achieved by a conventional oven,
Greatly reduce photonic crystal sensor material prepares threshold and cost；
(3) using the photonic crystal sensor material of the present invention to containing the structure containing hydrogen on dinitrogen heterocycle and a nitrogen
Compound it is easy to detect, it is simple to operate, without any pre-treatment, and respond rapid, high sensitivity, detection range is wide, profit
Detected with the photonic crystal sensor material of the present invention, 15min can obtain stable response signal, and detection range is 2 μ g/L-
512 μ g/L, lowest detection are limited to 0.76 μ g/L.
Other features and advantages of the present invention will be described in detail in subsequent specific embodiment part.
Brief description of the drawings
Exemplary embodiment of the invention is described in more detail in conjunction with the accompanying drawings, it is of the invention above-mentioned and its
Its purpose, feature and advantage will be apparent, wherein, in exemplary embodiment of the invention, identical reference number
Typically represent same parts.
Fig. 1 a and Fig. 1 b respectively illustrate glucose responding mechanism in the prior art and increase spreading out for PC with concentration of glucose
Penetrate peak red shift.
Fig. 2 shows preparation and the detection process schematic diagram of the PMMA-DMA PC according to the present invention.
Embodiment
The preferred embodiment of the present invention is more fully described below with reference to accompanying drawings.Although the present invention is shown in accompanying drawing
Preferred embodiment, however, it is to be appreciated that may be realized in various forms the present invention without the embodiment party that should be illustrated here
Formula is limited.On the contrary, these embodiments are provided so that the present invention is more thorough and complete, and can be by the present invention's
Scope is intactly communicated to those skilled in the art.
The first aspect of the present invention provides a kind of preparation method of photonic crystal sensor material, and the preparation method includes：
(1) in the presence of an inert gas, compound shown in compound shown in Formulas I, Formula II, water and initiator are contacted, entered
Row emulsifier-free emulsion polymerization reacts, and obtains polymer microballoon；
Wherein, R is the group containing alkylene, alkynes base, olefin amide base or alkene ester group；
(2) by the polymer microballoon and H2O2With HRP haptoreactions, PMD microballoons are obtained；
(3) disperse by the suspension of the PMD microballoons and stand heap to build, the photonic crystal sensor material is made.
In accordance with the present invention it is preferred that compound of formula I is compound shown in formula III,
Wherein, m be 2-10 integer, R1For covalent bond ,-CONH (CH2)p- or-COO (CH2)q-, p and q are independently of one another
For 0-10 integer, R2For C1-C10Alkyl.
Preferably, m be 2-5 integer, R1For-CONH (CH2)p, R2For C1-C5Alkyl.It is further preferred that
Compound shown in the formula III is 3- Methacrylamide base dopamines.
In accordance with the present invention it is preferred that relative to compound shown in formula every gram described I, the use of compound shown in the formula II
Measure as 0.1-0.2L, the dosage of the initiator is 2-5g.
In accordance with the present invention it is preferred that the temperature of the polymerisation is 70-90 DEG C, the time of polymerisation is 80-
120min。
In accordance with the present invention it is preferred that the initiator is KPS or APS (ammonium persulfate).
Under above-mentioned preferable DMA and MMA relative usage and polymerization reaction time, spherical best, the response of PMD microballoons
Rapidly.
In accordance with the present invention it is preferred that the method for step (1) includes：By compound, water shown in compound shown in formula I, formula II
Ultrasonic deoxygenation after mixing, then, under inert gas shielding, stir and be heated to 70-90 DEG C, finally, add initiator and carry out
Emulsifier-free emulsion polymerization reacts.
In accordance with the present invention it is preferred that step (3) includes：By the reacted product centrifugation washing of step (2), collect middle
Layer product and to be diluted to mass concentration be 0.1%-5%, pours into the container of heap base after ultrasonic disperse, is placed in 30-50 DEG C of baking oven
Middle standing, the photonic crystal sensor material is made.
The heap of photonic crystal sensor material, which is built, at present is carried out in special instrument-climatic chamber, a constant temperature
Constant humidity cabinet price 7000 rises；But the present invention is that the heap base of photonic crystal sensor material is carried out in a conventional oven, therefore significantly
Reduce and prepare threshold and cost.
The second aspect of the present invention provides a kind of photonic crystal sensor material as made from above-mentioned preparation method.
The third aspect of the present invention is described photonic crystal sensor material as dinitrogen heterocyclic compound detection reagent
Using, wherein, the dinitrogen heterocyclic compound is the compound with group shown in formula IV,
Preferably, photonic crystal sensor material provided by the invention can be used as Ciprofloxacin, Norfloxacin and
The detection reagent of Enoxacin.
As shown in Fig. 2 the piperazinyl group (that ring containing two N) of Ciprofloxacin (CF), can be under weak basic condition
Michael addition reaction occurs with quinone, can then be connected on photon crystal micro-ball, change the refractive index of photonic crystal, so as to draw
Play the decline of diffraction peak intensity.
It is by optimizing detection system, preferably pH=7.4 PBS cushioning liquid that the photon of the present invention is brilliant in detection
After reaching stabilization in the above-mentioned cushioning liquid of body sensing material immersion, the Ciprofloxacin standard for adding various concentrations from low to high successively is molten
Liquid, the i.e. concentration of Ciprofloxacin standard liquid are 0.01 μ g/L-2896 μ g/L, by the change for observing photonic crystal diffraction peak intensity
Change, it is 2 μ g/L-512 μ g/L to obtain the detection mark song range of linearity, and lowest detection is limited to 0.76 μ g/L.
The detection range of prior art HPLC-MS methods (LC-MS) is 5 μ g/L-60 μ g/L, thus, it can be known that of the invention
Detection range it is wider, sensitivity is higher；Moreover, the detection for actual sample fishpond water, without carrying out any pre-treatment, directly
Connect and add detection architecture, 15min can obtain stabilization signal, simple to operate, and response is rapid.
The present invention is further illustrated by the following examples.
Embodiment 1
20mg 3- Methacrylamide base dopamines (DMA) are dissolved in compound (MMA) shown in 3mL formulas II, then
The solution is added in 25.5mL deionized waters, ultrasonic deoxygenation 10min；Mechanical agitation, bath temperature 80 are carried out with 370rpm
DEG C, while logical nitrogen protection, after system temperature up to after 80 DEG C, adding initiator KPS, (60mg KPS are dissolved in 1.5mL deionizations
In water), continue to react 90min；After centrifugation removes supernatant, 1mL 0.1mM H are added into microballoon2O2And HRP (10.0mgHPR
It is dissolved in 0.50mL 0.10M PBS, pH 7.00), it is sufficiently mixed, ambient temperature overnight；It is then centrifuged for, washes, is centrifuged in 4000rpm
10min, supernatant precipitation is removed, only collects intermediate layer, that is, obtains PMD microballoons；
Obtained PMD microballoons are diluted to the suspension that mass fraction is 1% with deionized water, delayed after abundant ultrasonic disperse
Slowly pour into horizontal exhibition cylinder, be subsequently placed in 40 DEG C of baking ovens, stand 5-6 days, that is, obtain the photonic crystal with green gloss and pass
Feel material.
The photonic crystal sensor material is immersed in pH=7.4 PBS cushioning liquid after reaching stable, successively from low to high
The Ciprofloxacin standard liquid of various concentrations is added, i.e. the concentration of Ciprofloxacin standard liquid is 0.01 μ g/L-2896 μ g/L, is led to
The change of observation photonic crystal diffraction peak intensity is crossed, it is 2 μ g/L-512 μ g/L to obtain the detection mark song range of linearity, and lowest detection is limited to
0.76μg/L。
It is described above embodiments of the invention, described above is exemplary, and non-exclusive, and also not
It is limited to disclosed embodiment.In the case of the scope and spirit without departing from embodiment described, for the art
Those of ordinary skill for many modifications and changes will be apparent from.
Claims (10)
1. a kind of preparation method of photonic crystal sensor material, it is characterised in that the preparation method includes：
(1) in the presence of an inert gas, compound shown in compound shown in Formulas I, Formula II, water and initiator are contacted, carries out nothing
Soap emulsion polymerization, obtains polymer microballoon；
Wherein, R is the group containing alkylene, alkynes base, olefin amide base or alkene ester group；
(2) by the polymer microballoon and H2O2With HRP haptoreactions, PMD microballoons are obtained；
(3) disperse by the suspension of the PMD microballoons and stand heap to build, the photonic crystal sensor material is made.
2. the preparation method of photonic crystal sensor material according to claim 1, wherein, compound of formula I is shown in formula III
Compound,
Wherein, m be 2-10 integer, R1For covalent bond ,-CONH (CH2)p- or-COO (CH2)q-, p and q are each independently 0-
10 integer, R2For C1-C10Alkyl.
3. the preparation method of photonic crystal sensor material according to claim 2, wherein, compound shown in the formula III
For 3- Methacrylamide base dopamines.
4. the preparation method of photonic crystal sensor material according to claim 1, wherein, relative to the institute of formula every gram described I
Show compound, the dosage of compound shown in the formula II is 0.1-0.2L, and the dosage of the initiator is 2-5g.
5. the preparation method of photonic crystal sensor material according to claim 1, wherein, the temperature of the polymerisation is
70-90 DEG C, the time of polymerisation is 80-120min.
6. the preparation method of photonic crystal sensor material according to claim 1, wherein, the initiator be KPS or
APS。
7. the preparation method of photonic crystal sensor material according to claim 1, wherein, the method for step (1) includes：Will
Ultrasonic deoxygenation after compound shown in formula I, compound shown in formula II, water mixing, then, under inert gas shielding, stir and add
Heat arrives 70-90 DEG C, finally, adds initiator and carries out emulsifier-free emulsion polymerization reaction.
8. the preparation method of photonic crystal sensor material according to claim 1, wherein, step (3) includes：By step
(2) reacted product centrifugation washing, it is 0.1%-5% to collect intermediate layer product and be diluted to mass concentration, after ultrasonic disperse
Pour into heap to build in container, be placed in standing in 30-50 DEG C of baking oven, the photonic crystal sensor material is made.
9. photonic crystal sensor material made from the preparation method according to any one in claim 1-8.
10. application of the photonic crystal sensor material as dinitrogen heterocyclic compound detection reagent described in claim 9, wherein,
The dinitrogen heterocyclic compound is the compound with group shown in formula IV,
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108344713A (en) * | 2018-02-06 | 2018-07-31 | 军事科学院军事医学研究院环境医学与作业医学研究所 | Photonic crystal sensor material and its preparation method and application |
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| CN104634743A (en) * | 2013-11-14 | 2015-05-20 | 中国人民解放军军事医学科学院卫生学环境医学研究所 | Method for preparing visual photonic crystal sensor |
| CN105859933A (en) * | 2016-03-31 | 2016-08-17 | 北京化工大学 | Reactive polymer microsphere of core-shell structure, preparation method thereof and application thereof |
| CN106188437A (en) * | 2016-07-12 | 2016-12-07 | 江苏大学 | A kind of method that metal organic frame particle trace adsorbent is prepared in Pickering emulsion polymerization |
| CN106929915A (en) * | 2017-04-26 | 2017-07-07 | 北京市环境保护科学研究院 | A kind of opal photonic crystal of curved-surface structure and the preparation method of molecularly imprinted polymer inverse opal film |
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Patent Citations (4)
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| CN104634743A (en) * | 2013-11-14 | 2015-05-20 | 中国人民解放军军事医学科学院卫生学环境医学研究所 | Method for preparing visual photonic crystal sensor |
| CN105859933A (en) * | 2016-03-31 | 2016-08-17 | 北京化工大学 | Reactive polymer microsphere of core-shell structure, preparation method thereof and application thereof |
| CN106188437A (en) * | 2016-07-12 | 2016-12-07 | 江苏大学 | A kind of method that metal organic frame particle trace adsorbent is prepared in Pickering emulsion polymerization |
| CN106929915A (en) * | 2017-04-26 | 2017-07-07 | 北京市环境保护科学研究院 | A kind of opal photonic crystal of curved-surface structure and the preparation method of molecularly imprinted polymer inverse opal film |
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| RONG ZHANG ET AL.: "Specific and ultrasensitive ciprofloxacin detection by responsive photonic crystal sensor", 《JOURNAL OF HAZARDOUS MATERIALS》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108344713A (en) * | 2018-02-06 | 2018-07-31 | 军事科学院军事医学研究院环境医学与作业医学研究所 | Photonic crystal sensor material and its preparation method and application |
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