CN101899021B - Fluorescent compound and application thereof in detecting trace methylamphetamine - Google Patents
Fluorescent compound and application thereof in detecting trace methylamphetamine Download PDFInfo
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- CN101899021B CN101899021B CN2010102283721A CN201010228372A CN101899021B CN 101899021 B CN101899021 B CN 101899021B CN 2010102283721 A CN2010102283721 A CN 2010102283721A CN 201010228372 A CN201010228372 A CN 201010228372A CN 101899021 B CN101899021 B CN 101899021B
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Abstract
The present invention relates to a kind of fluorescent chemicals and its applications in detection trace crystal methamphetamine, it is characterised in that the fluorescent chemicals general structure are as follows:
R1, R2 are respectively triphenylamine in formula, and benzene, naphthalene, anthracene, pyrene, fluorenes, company's dinaphthyl, carbazole, benzothiophene, one of phenothiazinyl and rhodamine fluorescence substituent group and its derivative, R3 are alkyl substituent. Obvious fluorescent quenching can occur in a short time for the steam effect of fluorescent chemicals and crystal methamphetamine provided by the invention, the detection of p-Methylamphetamine can be realized according to being quenched for its fluorescence intensity, be the novel fluorescence sensing material of a kind of crystal methamphetamine detection. Detectable limit reaches 100ppb.
Description
Technical field
The present invention relates to one type of fluorescent chemicals and the application in detecting the trace methyl amphetamine thereof; One type of p-Methylamphetamine gas has the fluorescent sensing material that contains the diazosulfide group that rapid fluorescence responds or rather, belongs to the preparation field of organic fluorescence sensor material.
Background technology
Methyl amphetamine is commonly called as methamphetamine, is international, the domestic violated drugs that all receive strict control, and be one type and have strong excitation, appetite inhibiting effect and the gentle material that causes unreal effect, also be one of present most popular Drug abuse.Because its preparation low in raw material cost, synthetic technology is comparatively simple, is grasped by the lawless person easily, flows into society after illegal the preparation, the healthy and impairment public safety of harm humans.According to statistics, only the methamphetamine captured of 2008 1 year China just has 6.15 tons, if these drugs flow to society, its consequence will be very serious.But law enforcement agency lacks cost-effective testing tool in actual drugs fighting work, the main help that relies on narcotics agent's experience or rely on police dog in most drugs fighting works.Therefore, accurate detection of trace amphetamine drugs and Rapid Alarm are just become more and more urgent, set up a kind of simple rapid assay methods, become one of drugs fighting work problem demanding prompt solution.
The method that present commonly used being used to detects methyl amphetamine mainly contains the gas chromatography-mass spectrum technology used in conjunction, HPLC, Raman spectrum and immunization etc.Application gas chromatography-mass spectrum technology will be taked could use behind the extracting and enriching usually to sample, and the organic solvent of wherein using can cause secondary pollution to environment, is not suitable for field quick detection; HPLC complex equipments and loaded down with trivial details, sense cycle is long; The immunization reaction is slower, can not satisfy on-the-spot rapid determination.In view of above present Research, the detection method of developing new methamphetamine class material rapidly and efficiently is very necessary.Since fluorescent optical sensor have quick response, simple to operate, selectivity is high, detect low, the signal of limiting the quantity of directly perceived simple, disturb little and advantage such as be easy to distinguish, thereby be suitable for methyl amphetamine and detect.
The fluorescent material of excellent property is the basis of preparation fluorescent optical sensor, and organic materials inherent variety is that material chosen provides broad scope, through design, assembling and the cutting to organic molecular structure, can realize that the color from ruddiness to the blue light shows.Fluorescent material as sensing material should satisfy following requirement:
(1) excellent light stability is not easy to be bleached under high light, and fluorescence spectrum mainly is distributed in the 400-700nm visible region.
(2) good film-forming properties does not produce pin hole in the thin layer of tens nano thickness.
(3) can cause the variation (cancellation or enhancing) of material fluorescence with the specific action (like complexing, hydrogen bond, static, π-π, hydrophobic-hydrophobic interaction etc.) of material to be detected
The applicant intends proposition and contains the unitary fluorescent chemicals of diazosulfide unit structure for; And be used to detect methyl amphetamine; Such material compound method is simple, and chemically modified property is strong, through introducing the fluorescence functional group of different structure; Or increase the length of conjugated chain, can obtain the material of a series of solid-state stabilized illuminations.Because diazosulfide is a good electron acceptor, the methyl amphetamine molecule has certain characteristic electron of giving.When fluorescence molecule contacts with methyl amphetamine gas, transfer transport can take place, cause fluorescent quenching.Change through fluorescence can detect by p-Methylamphetamine steam in real time.Thereby be guided out design of the present invention
Summary of the invention
The object of the invention is to provide one type of fluorescent chemicals and the application aspect the detection methyl amphetamine thereof.The preparation method of fluorescent chemicals of the present invention is simple, productive rate is high, easily separated, purity is high, the response of gained fluorescent chemicals p-Methylamphetamine is sensitive, can detect the methyl amphetamine in the gas phase rapidly and accurately.
One type of fluorescent chemicals that is used to detect methyl amphetamine provided by the invention is characterized in that described fluorescent chemicals is to contain fluorophor and diazosulfide group, and its general structure is following:
N wherein
1Be the integer of 1-50, n
2Be the integer of 0-50, n is the integer of 1-5000.R
1, R
2Be respectively triphen amido, phenyl, naphthyl, anthryl, pyrenyl, fluorenyl, connect a kind of in fluorescence substituting group such as dinaphthyl, carbazyl, benzothienyl, phenothiazinyl, rhodamine and the verivate thereof, R
3Be alkyl substituent, R
1And R
2Be respectively fluorescent polymer and verivate thereof identical or inequality, R
2Even do not exist.
It all is that compound by bromo cpd and boracic ester or boric acid is under argon shield that described p-Methylamphetamine has the fluorescent chemicals of response; Forming through the Suzuki prepared in reaction, both can be that micromolecular compound also can be a high molecular polymer on structure.
Described p-Methylamphetamine has the fluorescent chemicals of response, under no methyl amphetamine existence condition, and its film or the stable performance of powder fluorescence radiation; In the presence of methyl amphetamine, its fluorescence changes, and generally shows as cancellation.Variation according to its fluorescence intensity can realize that p-Methylamphetamine detects.
Described p-Methylamphetamine has the compound of fluorescence response and methyl amphetamine to have the transfer transport effect, and the fluorophor of fluorescent chemicals and the benzene on the methyl amphetamine have π-π to interact and hydrophobic-hydrophobic interaction.The result of multiple effect causes the fluorescent quenching of fluorescent chemicals.
Details are as follows to adopt sensing material of the present invention to detect the process of the methyl amphetamine in the gas phase:
(1) through lifting or the method for spin coating and vapor deposition (glass, quartz, silicon chip, organic and polymeric solid carrier, microsphere, nano particle or pearl and nanofiber and nanotube etc.) preparation sense film in substrate.
(2) fluorescence spectrum and the light stability of test sense film.
(3) get a little methyl amphetamine and place the quartz cell bottom, fill up an absorbent cotton above it and avoid directly contacting with sense film, the quartz cell covered and enclosed is placed to be measured on one side.
(4) sense film is placed airtight quartz cell after, the fluorescence intensity of surveying its fluorescence maximum emission peak rapidly is with curve over time.
The present invention has following advantage:
(1) the prepared fluorescent chemicals that contains the diazosulfide structure, solution and solid film all have high luminous efficiency, and compound method is simple, and structure is prone to regulate, and is the ideal material of solid state fluorescence sensing diaphragm.
(2) the chemically modified property of sensing compound is strong, perhaps changes the fluorescent sensing material that the compound conjugated structure can easily obtain different emission through the kind of regulating and control luminophore.
(3) effect of gained fluorescent chemicals and methyl amphetamine is sensitive, can in 20 seconds, make quick response.
The embodiment of the invention 1 synthetic compound 1, polymkeric substance 2 and compound 3 are representative, have comprised the preparation method of the fluorescent chemicals of institute's desire protection, and with the detected result of these three kinds of fluorescent chemicalses retrieval trace methamphetamines.The ultimate value that detects can reach 100ppb.
With embodiment 2 is example [Fig. 4], has investigated the interaction of compound 1 with the methyl amphetamine saturation steam.Under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 20S cancellation 37%.
With embodiment 3 is example [Fig. 5], has investigated the interaction of polymkeric substance 2 with p-Methylamphetamine steam.Under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 20S cancellation 35%.
With embodiment 4 is example [Fig. 6], has investigated the interaction of compound 3 with the methyl amphetamine saturation steam.Under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 10S cancellation 10%.With embodiment 5 is example [Fig. 7]; Investigated the fluorescence situation (a air b methyl amphetamine c Tri N-Propyl Amine d aniline e to monomethylaniline) of flourescent sheet in different steam of polymkeric substance 2 preparations; At Tri N-Propyl Amine; Aniline and flourescent sheet fluorescence in the monomethylaniline do not had considerable change, and almost completely cancellation of fluorescence in methyl amphetamine steam.
In sum; The invention provides one type of fluorescent chemicals that can detect methyl amphetamine; Its constitutional features contains fluorophor and diazosulfide structural unit; This compounds can effectively suppress the solid-state fluorescent quenching problem that causes of assembling down of fluorescent material, and the solid state luminescent properties is good, with the steam effect of methyl amphetamine obvious fluorescent quenching can take place at short notice; Can realize the detection of p-Methylamphetamine according to the cancellation of its fluorescence intensity, be the novel fluorescence sensing material that one type of methyl amphetamine detects.
Description of drawings
Fig. 1 is the fluorescence emission spectrum of compound 1;
Fig. 2 is the fluorescence emission spectrum of polymkeric substance 2;
Fig. 3 is the fluorescence emission spectrum of compound 3;
Fig. 4 is that (curve is compound 1 maximum emission wavelength place fluorescence intensity (curve b) over time a) and in the methyl amphetamine steam for compound 1 autofluorescence stability;
Fig. 5 is that (curve is polymkeric substance 2 maximum emission wavelength place fluorescence intensities (curve b) over time a) and in the methyl amphetamine steam for polymkeric substance 2 autofluorescences stability;
Fig. 6 is that (curve is compound 3 maximum emission wavelength place fluorescence intensities (curve b) over time a) and in the methyl amphetamine steam for compound 3 autofluorescences stability;
Fig. 7 by the flourescent sheet of polymkeric substance 2 preparation through ultra violet lamp, the fluorescence (a air b methyl amphetamine c Tri N-Propyl Amine d aniline e is to monomethylaniline) that shows when meeting different steam.
Embodiment
Below in conjunction with specific embodiment and Figure of description, the present invention is done further elaboration.At first embodiment 1 has synthesized three kinds of fluorescent chemicalses, and embodiment 2-5 has set forth step and the result that compound 1, polymkeric substance 2, compound 3 detect the trace methamphetamines.
Embodiment 1 p-Methylamphetamine steam has the structure of compound of response as shown in table 1, and the compound method of the preferred compound of part is following.
(1) structure of compound 1 and synthetic (n
1=1, n
2=1, n=1, R
1=
R
3=-C
8H
17)
Weigh 322mg 9,9 - dioctylfluorene-2 ,7 - two acid pinacol ester and knit the brows bromomelatonin 214mg and 130mg benzothiadiazole IV - triphenylphosphine palladium catalyst is placed in the dual-port flask 50ml , deoxygenated with argon, and then degassed to which injecting 10ml of toluene as a solvent and added slowly to approximately 1mmol of K
2 CO
3 solution, 90 ℃ reaction 72h.Dichloromethane extraction is used in the washing back, on Rotary Evaporators, revolves extraction liquid dried then.The thick product that obtains through chromatographic column separate white solid compound 1.
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=8.02 (m, 4H), 7.94 (m, 2H), 7.92-7.90 (d, 2H), 7.79-7.77 (m, 2H), 7.73-7.70 (m, 2H), 2.11 (m, 4H), 1.17-1.10 (m, 20H), 0.88 (m, 4H), 0.77 (m, 6H).
The fluorescence emission spectrum of prepared compound 1 is as shown in Figure 1, and maximum emission wavelength is the synthetic (n of 530nm (2) polymkeric substance 2
1=1, n
2=0, n=1-5000, R
1=
R
3=-C
8H
17)
Weigh 322mg 9,9 - dioctylfluorene-2 ,7 - two knit the brows acid pinacol ester and 292mg II - bromo-benzo-thiadiazole and 130mg IV - triphenylphosphine palladium catalyst is placed in two-mouth bottle 50ml in deoxygenated with argon protection, and then degassed to which injecting 10ml of toluene as a solvent and added slowly to approximately 1mmol of K
2 CO
3 solution, 90 ℃ reaction 72h, extracting the organic phase was added dropwise 20ml of anhydrous methanol, and precipitated solid was filtered.Dissolve in the minimum of chloroform, splash in the anhydrous methanol and separate out, more than operation gets polymkeric substance 1 repeatedly several times.
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=8.11 (m, 2H), 8.06 (s, 2H), 7.98-7.90 (m, 4H), 2.10 (m, 4H), 1.41 (s, 1H), 1.19 (m, 23H), 0.81 (m, 4H), 0.77 (m, 7H).
The fluorescence emission spectrum of prepared polymkeric substance 2 is as shown in Figure 2, and emission maximum spectrum is the synthetic (n of 537nm (3) compound 3
1=0, n
2=1, n=1, R
1=R
2=
R
3=-OMe)
Preparing method and compound 1 synthetic similar.
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=8.3 (s, 2H), 8.0 (s, 4H), 7.95 (d, 2H), 7.87 (d, 2H), 7.47 (d, 2H), 7.42 (m, 2H), 7.32 (d, 8H), 7.22 (m, 2H), 3.85 (s, 6H), 3.10 (s, 6H).
The fluorescence emission spectrum of prepared compound 3 is as shown in Figure 3, and maximum emission wavelength is 481nm
Embodiment 2
Method through lifting prepares the sense film based on compound prepared among the embodiment 11 in the quartz plate substrate.The fluorescence spectrum and the light stability of test sense film.Place the quartz cell bottom to a methyl amphetamine, fill up an absorbent cotton above it and avoid directly contacting the quartz cell covered and enclosed with sense film.After sense film placed airtight quartz cell, survey the strong and change of time curve in its peak, fluorescence maximum emission peak place rapidly.As shown in Figure 4, under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 20s cancellation 37%.
Embodiment 3
Method through lifting prepares the sense film based on polymkeric substance prepared among the embodiment 12 in the quartz plate substrate.The fluorescence spectrum and the light stability of test sense film.Place the quartz cell bottom to a small amount of methyl amphetamine, fill up an absorbent cotton above it and avoid directly contacting the quartz cell covered and enclosed with sense film.After sense film placed airtight quartz cell, survey the strong and change of time curve in its peak, fluorescence maximum emission peak place rapidly.As shown in Figure 5, under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 20s cancellation 35%.
Embodiment 4
Method through lifting prepares the sense film based on compound prepared among the embodiment 13 in the quartz plate substrate.The fluorescence spectrum and the light stability of test sense film.Place the quartz cell bottom to a small amount of methyl amphetamine, fill up an absorbent cotton above it and avoid directly contacting the quartz cell covered and enclosed with sense film.After sense film placed airtight quartz cell, survey the strong and change of time curve in its peak, fluorescence maximum emission peak place rapidly.As shown in Figure 6, under the methyl amphetamine saturation steam, the intensity of the maximum emission peak of its film in 10s cancellation 10%.
Embodiment 5
Method through lifting prepares the sense film based on compound prepared among the embodiment 12 in the quartz plate substrate.Quartz plate is placed into respectively in the fluorescence pond of containing different steam, under luminescent lamp, observes its change in fluorescence.As shown in Figure 7, almost completely cancellation of fluorescence (b among the figure) in methyl amphetamine steam.
Although describe the present invention in conjunction with the preferred embodiments, the present invention is not limited to the foregoing description, should be understood that these embodiment only be used to the present invention is described and be not used in the restriction scope of the present invention.Conceive under the guiding in the present invention, it should be appreciated by one skilled in the art that the certain change to the various embodiments of the present invention scheme is carried out all will be covered by spirit of claims of the present invention and scope.
Claims (4)
1. the application of fluorescent chemicals, said fluorescent chemicals is:
It is characterized in that being used for detecting the methyl amphetamine of gas phase; π-π takes place and interacts and hydrophobic-hydrophobic interaction in the fluorophor of described fluorescent chemicals and the benzene of methyl amphetamine; The fluorescence generation cancellation of described fluorescent chemicals under the methyl amphetamine existence condition realizes the detection of p-Methylamphetamine according to the variation of its fluorescence intensity.
2. by the described application of claim 1, it is characterized in that detecting step and be:
(1) through lift, the method for spin coating or vapor deposition prepares sense film in the substrate of glass, quartz, silicon chip, polymeric solid carrier, microsphere, nano particle, nanofiber or nanotube;
(2) fluorescence spectrum and the light stability of test sense film;
(3) get a little methyl amphetamine as for the quartz cell bottom, fill up an absorbent cotton above it and avoid directly contacting with sense film, the quartz cell covered and enclosed is placed to be measured on one side;
(4) sense film is placed airtight quartz cell after, the fluorescence intensity of surveying its fluorescence maximum emission peak rapidly is curve over time.
3. by the described application of claim 1, it is characterized in that described fluorescent chemicals and methyl amphetamine in 20 seconds, the intensity cancellation 40% of fluorescence maximum emission peak.
4. the described application of claim 1 is characterized in that the ultimate value of described fluorescent chemicals detection trace methyl amphetamine reaches 100ppb.
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| EP3701249A4 (en) * | 2017-10-26 | 2021-07-21 | The University of Queensland | Detection method |
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| CN105548098B (en) * | 2015-12-03 | 2018-07-13 | 中国科学院上海微系统与信息技术研究所 | A kind of fluorescence probe and detection method detecting crystal methamphetamine or/and ketamine |
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| CN106977700B (en) * | 2017-03-30 | 2019-04-12 | 苏州大学 | The fluorescence conjugated macromolecule for detecting fragrant amine aqueous solution senses system, preparation method and application |
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| CN112414976A (en) * | 2019-08-20 | 2021-02-26 | 吉林大学 | Application of triphenylamine compound as benzene series detection agent |
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| CN113087637B (en) * | 2021-03-30 | 2022-07-19 | 中国科学院上海微系统与信息技术研究所 | Fluorescent sensing material for detecting methamphetamine and method for detecting methamphetamine |
| CN113461492B (en) * | 2021-06-30 | 2022-11-11 | 中国科学院上海微系统与信息技术研究所 | Liquid-phase fluorescence detection system based on selective depolymerization of chiral crystal interface |
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