CN110156734A - A kind of fluorescence probe, fluorescent test paper and preparation method thereof for simulating analyte detection for nerve gas - Google Patents
A kind of fluorescence probe, fluorescent test paper and preparation method thereof for simulating analyte detection for nerve gas Download PDFInfo
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- CN110156734A CN110156734A CN201910309692.0A CN201910309692A CN110156734A CN 110156734 A CN110156734 A CN 110156734A CN 201910309692 A CN201910309692 A CN 201910309692A CN 110156734 A CN110156734 A CN 110156734A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- G01N21/62—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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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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
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
Abstract
The present invention discloses a kind of fluorescence probe, fluorescent test paper and preparation method thereof that analyte detection is simulated for nerve gas, and the structural formula of the fluorescence probe for nerve gas simulation analyte detection isWherein, R is located at any the position of substitution on the phenyl ring of place, R H, OCH3Or Cl.Fluorescence probe of the invention has fluorescent specific to halophosphate class nerve gas, and phosphor dot lit fluorescence sense can be carried out to it, detects to realize to it, and detection sensitivity is high, and detection limit is low；Fluorescent test paper made from it can be used to halophosphate class nerve gas in detection gas atmosphere, and detection method is simple, and fluorescent test paper preparation cost is low, and is convenient for carrying.
Description
Technical field
The present invention relates to small-molecule fluorescent probe field more particularly to a kind of fluorescence for nerve gas simulation analyte detection
Probe, fluorescent test paper and preparation method thereof.
Background technique
Sarin (sarin, GB), soman (soman, GD) are two kinds of representative nerve gas, are halogen phosphoric acid
Ester；This kind of compound can with the acetylcholinesterase in human central nervous occur it is irreversible react, to destroy neural punching
Dynamic, can cause the symptoms such as asphyxia, sudden cardiac arrest in a few minutes leads to death；And it is largely used to from a this kind of compound of postwar
In chemical weapons and pesticide.Therefore, the method for sensing that research and development quickly accurately detect halophosphate class nerve gas has extremely heavy
The meaning wanted.
Short, high sensitivity, time and spatial resolution are high as a kind of response time for fluorescence sense method, visually detect
Means have been widely used for various environmental parameters, the quantitative and qualitative detection of biochemical substrates.It is reported, with chlorine p diethylaminobenzoic acid
Ester (diethyl chlorophosphate, DCP) is nerve gas analogies, is applied to halophosphate class nerve gas and detects
Fluorescent material include conjugated polymer, small molecule fluorescent material, biological marking material, gathering induced luminescence material and nanometer material
Material etc., compared to other materials, small molecule material has many advantages, such as that at low cost, synthetic method is simple；But it is applied to halogen phosphorus at present
The small molecule fluorescent material of esters of gallic acid nerve gas detection is still less, and cannot prepare fluorescent test paper with low cost.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide one kind simulates analyte detection for nerve gas
Fluorescence probe, fluorescent test paper and preparation method thereof, it is intended to solve existing applied to the small of halophosphate class nerve gas detection
Molecular fluorescence material is still less, and the problem of cannot prepare fluorescent test paper with low cost.
Technical scheme is as follows:
A kind of fluorescence probe for nerve gas simulation analyte detection, the fluorescence for nerve gas simulation analyte detection
The structural formula of probe isWherein, R is located at any the position of substitution on the phenyl ring of place, R
For H, OCH3Or Cl.
The fluorescence probe for nerve gas simulation analyte detection, wherein R=H.
A kind of preparation method of the fluorescence probe as described above for nerve gas simulation analyte detection, wherein including step
It is rapid:
A, 2- hydroxy acetophenone, 4- (diethoxymethyl) benzaldehyde and the inorganic base that R replaces are placed in polar solvent, are added
12~36h of heat reflux；It is cooled to room temperature addition hydrogen peroxide, 12~36h is stirred at room temperature, is subsequently added into excessive hydrochloric acid stirring, warp
Concentration, column chromatography, obtain fluorescence probe intermediate；
B, fluorescence probe intermediate and hydroxylamine hydrochloride are in CH2Cl2Middle 4~36h of back flow reaction, concentrated, recrystallization, obtains
Fluorescence probe.
The preparation method of the fluorescence probe for nerve gas simulation analyte detection, wherein in step A, the nothing
Machine alkali is KOH or NaOH；The polar solvent is methanol, ethyl alcohol or ethylene glycol.
The preparation method of the fluorescence probe for nerve gas simulation analyte detection, wherein in step A, the R is taken
The 2- hydroxy acetophenone in generation, 4- (diethoxymethyl) benzaldehyde, inorganic base, hydrogen peroxide molar ratio be 1:3~5:5~40:
10~50.
The preparation method of the fluorescence probe for nerve gas simulation analyte detection, wherein described glimmering in step B
The molar ratio of light probe intermediate and hydroxylamine hydrochloride is 1:2~10.
A kind of preparation method of the fluorescent test paper for nerve gas simulation analyte detection, wherein comprising steps of
C, the fluorescence probe for being used for nerve gas simulation analyte detection as claimed in claim 1 or 2 is set with host material
In organic solvent, it is uniformly mixed；
D, then above-mentioned mixed liquor is laid in substrate, drying film forming is cut to obtain the final product.
The preparation method of the fluorescent test paper for nerve gas simulation analyte detection, wherein in step C, the use
In nerve gas simulation analyte detection fluorescence probe and host material weight ratio be 1:10~1000；The host material is
PEG, PP or PB；The boiling point of the organic solvent is lower than 100 DEG C.
A kind of fluorescent test paper for nerve gas simulation analyte detection, wherein using as described above for nerve gas
The preparation method for simulating the fluorescent test paper of analyte detection is made.
The utility model has the advantages that fluorescence probe structure novel of the invention, with fluorescence quantum yield height, good light stability, light emitting machine
Managing flavone dye clear, convieniently synthesized, that toxicity is low is fluorescence probe parent, is rolled into a ball with the oximido of high reaction activity as halophosphate
The recognition group of class nerve gas, realization carry out phosphor dot lit fluorescence sense to it, to realize to halophosphate class nerve
The detection of poison gas；Fluorescence probe of the invention has fluorescent specific to halophosphate class nerve gas, can be used directly to molten
Halophosphate class nerve gas in liquid carries out qualitative and quantitative analysis, high sensitivity, and detection limits low；The examination of fluorescence made from it
Paper can be used to halophosphate class nerve gas in detection gas atmosphere, and detection method is simple, and the preparation cost of fluorescent test paper is low, side
Portable belt.
Detailed description of the invention
Fig. 1 be in the embodiment of the present invention 1 HOFO to the fluorescence response of the solution to be measured containing various concentration DCP at any time
Variation diagram.
Fig. 2 is HOFO in the embodiment of the present invention 1 to the fluorescence response figure of the solution to be measured containing various concentration DCP.
Fig. 3 is that HOFO rings the fluorescence of the solution to be measured containing different compounds (concentration is identical) in the embodiment of the present invention 1
Answer comparison diagram.
Fig. 4 is atmosphere of the solid-state HOFO in the fluorescent test paper in the embodiment of the present invention 1 to different DCP vapour concentrations
Fluorescence response figure.
Fig. 5 is the solid-state HOFO in the fluorescent test paper in the embodiment of the present invention 1 to different compound steams (vapour concentration phase
Fluorescence response comparison diagram together).
Specific embodiment
The present invention provides a kind of fluorescence probe, fluorescent test paper and preparation method thereof that analyte detection is simulated for nerve gas,
To make the purpose of the present invention, technical solution and effect clearer, clear and definite, the present invention is described in more detail below.It should
Understand, the specific embodiments described herein are merely illustrative of the present invention, is not intended to limit the present invention.
The present invention provides a kind of fluorescence probes for nerve gas simulation analyte detection, wherein described to be used for Nervous toxicity
The structural formula of fluorescence probe of gas simulation analyte detection isWherein, R is located at place phenyl ring
On any the position of substitution, R H, OCH3Or Cl；Further, R=H.
Fluorescence probe structure novel of the invention, with fluorescence quantum yield height, good light stability, luminescence mechanism is clear, closes
It is fluorescence probe parent at the low flavone dye of easy, toxicity, with the oximido group of high reaction activity for halophosphate class Nervous toxicity
The recognition group of gas；The oxime hydroxyl of fluorescence probe i.e. of the invention can be used as nucleopilic reagent attack halophosphate class nerve gas
Center phosphorus (V), so that photo induced electron transfer (the photo induced electron between oxime substituent group and lavonoid backbone
Transfer, PET) process be suppressed cause fluorescence enhancement, the fluorescence sense to halophosphate class nerve gas is realized with this, from
And it realizes and it is detected.Fluorescence probe of the invention is more convenient for as phosphor dot lit sensor compared with fluorescent quenching formula sensor naked
Eye observation, more meets the requirement accurately detected to halophosphate class nerve gas.
The present invention also provides one kind to be used for the preparation method that nerve gas simulates the fluorescence probe of analyte detection as described above,
Wherein, comprising steps of
A, 2- hydroxy acetophenone, 4- (diethoxymethyl) benzaldehyde and the inorganic base that R replaces are placed in polar solvent, are added
12~36h of heat reflux；It is cooled to room temperature addition hydrogen peroxide, 12~36h is stirred at room temperature, is subsequently added into excessive hydrochloric acid stirring, warp
Concentration, column chromatography, obtain fluorescence probe intermediate；
B, fluorescence probe intermediate and hydroxylamine hydrochloride are in CH2Cl2Middle 4~36h of back flow reaction, concentrated, recrystallization, obtains
Fluorescence probe.
The preparation route of the fluorescence probe for nerve gas simulation analyte detection of the invention is
The present invention first passes through " one pot of two-step method " successively by Claisen-Schmidt condensation reaction, Algar-Flynn-
Oyamada oxidative cyclization reaction low cost is obtained fluorescence probe intermediate (flavonoids dyestuff)；It is condensed using Schiff base
Fluorescence probe is prepared in reaction.Further, in step A, the inorganic base is KOH or NaOH；The polar solvent be methanol,
Ethyl alcohol or ethylene glycol；2- hydroxy acetophenone that the R replaces, 4- (diethoxymethyl) benzaldehyde, inorganic base, hydrogen peroxide rub
You are than being 1:3~5:5~40:10~50；The eluant, eluent of the column chromatography is the n-hexane and acetic acid that volume ratio is 10~4:1
The mixed solvent of ethyl ester.In step B, the molar ratio of the fluorescence probe intermediate and hydroxylamine hydrochloride is 1:2~10；The heavy knot
Brilliant solvent is tetrahydrofuran (THF).
The preparation method of fluorescence probe of the invention is simple, at low cost, suitable for carrying out expanding production in practice.
The present invention also provides a kind of preparation methods of fluorescent test paper for nerve gas simulation analyte detection, wherein including
Step:
C, the fluorescence probe for being used for nerve gas simulation analyte detection as described above and host material are placed in organic solvent
In, it is uniformly mixed；
D, then above-mentioned mixed liquor is laid in substrate, drying film forming is cut to obtain the final product.
Further, in step C, the host material may be selected from but not limited to polyethylene glycol (Polyeth ylene
Glycol, PEG), it is polypropylene (Polypropylene, PP), a kind of in polybutadiene (polybutadi ene, PB)；The use
In nerve gas simulation analyte detection fluorescence probe and host material weight ratio be 1:10~1000；The boiling of the organic solvent
Point is lower than 100 DEG C, ethyl acetate.In step D, the substrate may be selected from but not limited to one of sheet glass, quartz plate；
The drying temperature is 60~90 DEG C.
The present invention also provides a kind of fluorescent test papers for nerve gas simulation analyte detection, wherein using as described above
The preparation method of fluorescent test paper for nerve gas simulation analyte detection is made.
Present invention use is first swollen the preparation method dried afterwards and prepares fluorescent test paper, simple and convenient, it is easy to accomplish, it is suitable for real
Expand large-scale production in border；The present invention substantially reduces the use of fluorescence probe using cheap high molecular material as host material
Amount, further reduced production cost.The fluorescent test paper that the present invention is prepared is maintained to halophosphate class nerve gas
Compared with high detection sensitivity, it is convenient for carrying.The method of halophosphate class nerve gas, simple and convenient in detection gas of the invention.
Below by embodiment to the fluorescence probe of the fluorescent test paper for nerve gas simulation analyte detection of the invention, glimmering
The preparation method and its performance of light test paper are described in detail.
Embodiment 1
(1) 2- hydroxy acetophenone (40mmol) and terephthaldehyde's acetal aldehyde (160mmol) are dissolved in ethyl alcohol, are subsequently added into
KOH (400mmol), heating reflux reaction for 24 hours, are cooled to room temperature；The reaction was continued afterwards for addition hydrogen peroxide (20mL) for 24 hours, adds hydrochloric acid extremely
Solvent is removed under reduced pressure after stirring 5min in pH=1, and through column chromatography, (eluant, eluent is that the normal hexane that volume ratio is 7:1 and ethyl acetate are mixed
Bonding solvent) fluorescence probe intermediate 4- (3- hydroxyl -4- oxo -4H- chromene -2- base) benzaldehyde (referred to as HOFA) is obtained, it produces
Rate is 45%, and the structural formula of the fluorescence probe intermediate is 1H-NMR(600MHz,DMSO-d6),
δ: 10.09 (br s, 2H), 8.44 (d, J=8.2Hz, 2H), 8.13 (d, J=7.9Hz, 1H), 8.09 (d, J=8.2Hz, 2H),
7.84 (t, J=7.7Hz, 1H), 7.80 (d, J=8.3Hz, 1H), 7.49 (t, J=7.4Hz, 1H)13C-NMR(150MHz,
DMSO-d6),δ:192.77,173.27,154.71,143.54,140.41,136.25,134.16,129.54,128.10,
124.78,121.29,118.57。MS(HR ESI-TOF):m/z calcd for C16H10O4: 266.0652, found [M+H]+:
267.0647。
(2) back flow reaction for 24 hours, is depressurized after cooling and is removed in methylene chloride for HOFA (4mmol) and hydroxylamine hydrochloride (20mmol)
Solvent is removed, fluorescence probe 4- (3- hydroxyl -4- oxo -4H- chromene -2- base) benzaldoxime is recrystallized to give in THF (referred to as
HOFO), the structural formula of yield 89%, the fluorescence probe is 1H-NMR(600MHz,
), DMSO-d6 δ: 9.62 (s, 1H), 8.18 (d, J=8.3Hz, 2H), 8.09 (d, J=8.0Hz, 1H), 7.79-7.73 (m,
2H), 7.71 (s, 1H), 7.61 (d, J=8.4Hz, 2H), 7.44 (t, J=7.4Hz, 1H), 7.05 (br s, 1H)13C-NMR
(150MHz,DMSO-d6),δ:172.86,154.57,145.16,139.05,137.98,136.76,133.75,129.81,
127.87,125.00,124.82,124.60,121.36,118.44.MS(HR ESI-TOF):m/z calcd for
C16H11O4N:281.0761,found[M+H]+:282.0754。
It (3) is halophosphate class nerve gas with diethyl chloro-phosphate (diethyl chlorophosphate, DCP)
Analogies test in solution HOFO to the fluorescence response of halophosphate class nerve gas.
HOFO is dissolved in the HOFO solution that methanol prepares 4 parts of same concentrations (0.01mM)；It is separately added into 4 parts of HOFO solution
Different amounts of DCP obtains 4 parts of solution to be measured of the DCP containing various concentration, the concentration of DCP be respectively 0.05mM, 0.2mM,
0.4mM,0.8mM；Then fluorescence spectrum test carried out respectively to above-mentioned solution to be measured, HOFO to containing various concentration DCP to
The fluorescence response for surveying solution changes with time as shown in Figure 1, it is known that HOFO has tended to completely, show to the response of DCP after 60s
HOFO has the very fast speed of response to DCP.HOFO solution (0.01mM) is excited with the light of 365nm, as DCP in HOFO solution
Concentration increase to 0.8mM from 0, HOFO is to the fluorescence response of various concentration DCP as shown in Fig. 2, HOFO is located at the fluorescence of 560nm
Emission peak increases constantly enhancing with the concentration of DCP, and HOFO limits up to 1.3ppb (i.e. 7.8nmol/L) detection of DCP；To 5 parts
Chloroethene diethyl phthalate (Diethyl chlorophosphate, DCP), cyano phosphoric acid are separately added into HOFO solution (0.01mM)
Diethylester (Diethyl cyanophosphonate, DCNP), dimethyl methyl phosphonate (Dimethyl
Methylphosphonate, DMMP), triethyl phosphate (Triethyl phosphate, TEP), acetic acid (Acetic acid
Glacial, AcOH), 5 parts of different solution to be measured (concentration of above-mentioned 5 kinds of compounds is 0.8mM) is obtained, with the light of 365nm
Solution to be measured is excited, HOFO is as shown in Figure 3 to the fluorescence response of above-mentioned 5 kinds of compounds, it is known that the fluorescence probe is in solution
DCP shows specificly-response.
(4) preparation of fluorescent test paper.
With PEG (Mw=10000) for host material, 1g PEG is dissolved in 300mL ethyl acetate, and 50mg is added
HOFO, heating are poured into it on sheet glass after mixing, and film forming is dried at 60 DEG C, needs to be cut into suitable shape according to experiment
The fluorescent test paper of the HOFO load of shape (such as rectangle).
(5) fluorescent test paper of HOFO load tests the detection performance of DCP steam.
The HOFO fluorescent test paper loaded is placed in 10~600s (such as 60s) in the atmosphere of different DCP vapour concentrations,
Solid-state HOFO in fluorescent test paper is as shown in Figure 4 to the spectral response of DCP steam, it is known that the fluorescence intensity of solid-state HOFO is with DCP
Vapor concentration variation is still incremental, wherein insertion figure is the fluorescent test paper before test and the fluorescent test paper after test portable ultraviolet
Fluorescence contrast under lamp is as a result, the solid-state HOFO in fluorescent test paper limits up to 2.6ppb the detection of DCP steam；In fluorescent test paper
Solid-state HOFO to fluorescence response comparing result such as Fig. 5 institutes of different compound steams (compound steam concentration is 120ppm)
Show, it is known that the solid-state HOFO in fluorescent test paper still has specificly-response to DCP.
In conclusion it is provided by the invention it is a kind of for the nerve gas simulation fluorescence probe of analyte detection, fluorescent test paper and
Preparation method, fluorescence probe structure novel of the invention, with fluorescence quantum yield height, good light stability, luminescence mechanism it is clear,
The flavone dye convieniently synthesized, toxicity is low is fluorescence probe parent, and the oximido group with high reaction activity is halophosphate class nerve
The recognition group of poison gas, realization carry out phosphor dot lit fluorescence sense to it, to realize to halophosphate class nerve gas
Detection；Fluorescence probe of the invention has fluorescent specific to halophosphate class nerve gas, can be used directly to in solution
Halophosphate class nerve gas carries out qualitative and quantitative analysis, high sensitivity, and detection limits low；Fluorescent test paper made from it is available
Carry out halophosphate class nerve gas in detection gas atmosphere, detection method is simple, and fluorescent test paper preparation cost is low, is convenient for carrying.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of fluorescence probe for nerve gas simulation analyte detection, which is characterized in that the structural formula of the fluorescence probe isWherein, R is located at any the position of substitution on the phenyl ring of place, R H, OCH3Or Cl.
2. the fluorescence probe according to claim 1 for nerve gas simulation analyte detection, which is characterized in that R=H.
3. a kind of preparation method for the fluorescence probe of nerve gas simulation analyte detection as claimed in claim 1 or 2, special
Sign is, comprising steps of
A, 2- hydroxy acetophenone, 4- (diethoxymethyl) benzaldehyde and the inorganic base that R replaces are placed in polar solvent, are heated back
Flow 12~36h；It is cooled to room temperature addition hydrogen peroxide, 12~36h is stirred at room temperature, excessive hydrochloric acid is subsequently added into and stirs, concentrated,
Column chromatography, obtains fluorescence probe intermediate；
B, fluorescence probe intermediate and hydroxylamine hydrochloride are in CH2Cl2Middle 4~36h of back flow reaction, concentrated, recrystallization, obtains fluorescence
Probe.
4. the preparation method of the fluorescence probe according to claim 3 for nerve gas simulation analyte detection, feature exist
In in step A, the inorganic base is KOH or NaOH；The polar solvent is methanol, ethyl alcohol or ethylene glycol.
5. the preparation method of the fluorescence probe according to claim 3 for nerve gas simulation analyte detection, feature exist
In, in step A, 2- hydroxy acetophenone that the R replaces, 4- (diethoxymethyl) benzaldehyde, inorganic base, hydrogen peroxide mole
Than for 1:3~5:5~40:10~50.
6. the preparation method of the fluorescence probe according to claim 3 for nerve gas simulation analyte detection, feature exist
In in step B, the molar ratio of the fluorescence probe intermediate and hydroxylamine hydrochloride is 1:2~10.
7. a kind of preparation method of the fluorescent test paper for nerve gas simulation analyte detection, which is characterized in that comprising steps of
C, the fluorescence probe for being used for nerve gas simulation analyte detection as described in claim 1 is placed in host material organic molten
In agent, it is uniformly mixed；
D, then above-mentioned mixed liquor is laid in substrate, drying film forming is cut to obtain the final product.
8. the preparation method of the fluorescent test paper according to claim 7 for nerve gas simulation analyte detection, feature exist
In, in step C, it is described for nerve gas simulation analyte detection fluorescence probe and host material weight ratio be 1:10~
1000；The host material is PEG, PP or PB；The boiling point of the organic solvent is lower than 100 DEG C.
9. the preparation method of the fluorescent test paper according to claim 8 for nerve gas simulation analyte detection, feature exist
In in step D, the substrate is sheet glass or quartz plate.
10. a kind of fluorescent test paper for nerve gas simulation analyte detection, which is characterized in that any using such as claim 7~9
The preparation method of the fluorescent test paper for nerve gas simulation analyte detection is made.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111269251A (en) * | 2020-03-10 | 2020-06-12 | 中国科学技术大学 | Fluorescent probe and test paper of nerve agent simulant and preparation method thereof |
| CN112300202A (en) * | 2020-11-03 | 2021-02-02 | 中国人民解放军61699部队 | Fluorescent probe, nerve toxin detection element, preparation method and application |
| CN113004258A (en) * | 2019-12-20 | 2021-06-22 | 湖南超亟化学科技有限公司 | Preparation method and application of hydrogen sulfide ratio type fluorescent molecular probe based on ESIPT effect |
| CN115403514A (en) * | 2022-09-29 | 2022-11-29 | 中国科学院上海微系统与信息技术研究所 | Compound and application thereof in detection of organophosphate nerve agent simulant product |
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