CN101417989A - Anion receptor based on nitrofuran formyl hydrazone and phenolic hydroxyl and preparation and use of organagel thereof - Google Patents
Anion receptor based on nitrofuran formyl hydrazone and phenolic hydroxyl and preparation and use of organagel thereof Download PDFInfo
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- CN101417989A CN101417989A CNA2008101854776A CN200810185477A CN101417989A CN 101417989 A CN101417989 A CN 101417989A CN A2008101854776 A CNA2008101854776 A CN A2008101854776A CN 200810185477 A CN200810185477 A CN 200810185477A CN 101417989 A CN101417989 A CN 101417989A
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Abstract
The invention provides an anion receptor based on 5-nitrofuran formyl hydrazone and phenolic hydroxyl. The anion receptor is obtained by mixing 2, 6-dimethylacyl-4-chlorophenol and 5-(4-nitro)-phenyl-2-benzoyl diazanyl furan according to certain proportion, stirring and refluxing the mixture for 3 to 8 hours at a temperature of between 70 and 100 DEG C by using anhydrous ethanol as a solvent and p-toluene sulfonic acid as a catalyst, distilling out most of the solvent through reducing the pressure, performing suction filtration after cooling, and performing recrystalization on the solid product by using DMSO-EtOH. The anion receptor has color comparison recognizing ability on fluorion, acetic acid radical and phosphoric acid dihydrogen radical in a DMSO solution. The anion receptor is dissolved in DMF to be prepared into 0.5 to 2.0 percent of solution which is cooled to room temperature to be prepare into stable anion receptor organic gel used for performing colorimetric detection on the fluorion, and the acetic acid radical and phosphoric acid dihydrogen radical ions in the DMSO solution. The anion receptor has the advantages of convenience for carrying, convenient use, high detection sensitivity and the like.
Description
Technical field
The invention belongs to chemical technology field, relate to a kind of anion receptor based on nitrofuran formyl hydrazone and phenolic hydroxyl group and preparation method thereof, the invention still further relates to the preparation of this anion receptor organogel and in the application of negatively charged ion context of detection.
Background technology
Negatively charged ion has basic effect in life system, environmental system and Chemical Manufacture.Especially in the life system, negatively charged ion has important effect to the realization of vital process.Therefore, anionic detection is a very necessary job.Such as, fluorion is a kind of negatively charged ion that the life system is had material impact.As everyone knows, human body is taken in an amount of fluorion can preventing dental caries, prevents osteoporosis.Yet excessive absorption fluorion can cause fluorosis, the ameloblast of slight fluorosis harm people tooth bud, and serious fluorosis can cause bone generation fluorine osteosclerosis, sclerotin hardening, hyperosteogeny, make the osteoarthrosis limitation of activity, even hunch, paralysis, completely lose work capacity.Therefore, qualitative and quantitative detection fluorion is a very important problem.Generally, fluorion can by ion selective electrode and
19The F nuclear magnetic resonance, detects, and these methods need expensive instrument and complicated test procedure.Therefore, developing conveniently the fluorion detection method has been subjected to people and has more and more paid close attention to.
In numerous analysing and detecting method, produce colour-change and come qualitative and the method detection by quantitative determinand is that colorimetry is a kind of method the most easily by testing sample and the detection reagent back that reacts.Utilizing colorimetry identification negatively charged ion is the focus of present supramolecular chemistry field people research.At present people developed some can be in solution the anionic transmitter of colorimetric detection.But the colorimetric detection negatively charged ion still needs obtain solution in the solution, and solution inconvenience is carried and preserved.Comparatively speaking, if develop the organogel that to stablize the anionic colorimetric detection of depositing and being easy to carry about with one, preserving and using, using value will be arranged more.
Summary of the invention
The purpose of this invention is to provide a kind of anion receptor based on nitrofuran formyl hydrazone and phenolic hydroxyl group;
Another object of the present invention provides the preparation method of this anion receptor;
A further object of the invention just provides the application of this anion receptor in detecting negatively charged ion.
The present invention more has a purpose, just provides a kind of preparation and the application in detecting negatively charged ion thereof of this anion receptor organogel.
One, based on the anion receptor of nitrofuran formyl hydrazone and phenolic hydroxyl group
The structural formula of anion receptor compound of the present invention is as follows:
The constructional feature of anion receptor of the present invention: this receptor compound is the acyl hydrazone derivative of phenol, has symmetrical pincerlike structure.Amido (N-H) and the methylene radical (HC=N) on the acylhydrazone in phenolic hydroxyl group in this compound (O-H), the acylhydrazone can be as hydrogen bond donor type recognition sites.Simultaneously, the p-nitrophenyl furans is a chromophoric group.This compound has possessed the structure of typical Anion Recognition acceptor, has good Anion Recognition ability.In addition, contain hydrogen bond receptor groups such as aforesaid hydrogen bond donor group and nitro acyl group in this compound molecule, therefore, this compound can form intermolecular hydrogen bond with solvent, becomes xanthan molecule thereby become a kind of good low molecular weight organic gel.
Two, the preparation of anion receptor compound
The preparation of anion receptor compound of the present invention is finished by following processing step:
Be with intermediate 2; 6-diformyl-4-chlorophenol and 5-((4-nitro) phenyl-2-benzoyl diazanyl) furans joins in the reactor with 1: 2～2.5 mol ratio; the dehydrated alcohol that adding reactant total mass is 10～30 times is made the tosic acid of solvent, reactant total mass 0.001～0.01% and is made catalyzer; in 70～100 ℃ of following stirring and refluxing after 3～8 hours; decompression steams most of solvent; cooling back suction filtration, solid product with dimethyl sulfoxide (DMSO)-ethyl alcohol recrystallization promptly.Its concrete synthetic route is as follows:
Wherein intermediate 2, and 6-diformyl-4-chlorophenol is by following prepared:
(1) 2, the preparation of 6-dihydroxymethyl-4-chlorophenol: para-chlorophenol and Paraformaldehyde 96 are mixed with 1: 0.5～0.6 mass ratio, add the sodium hydroxide powder of reactant total mass 10～15%, slowly be heated to 50～60 ℃ after mixing, the fusion of 4-chlorophenol, Paraformaldehyde 96 is suspended in wherein, stir 0.5～2h, reaction solution is khaki color and then becomes red-purple, continues to stir 2～5h, the reactant caking, reaction terminating; The reaction mixture of caking is dissolved in the methyl alcohol of heat of 20～50 times of reactant total masses, transfers PH to 2～3 with hydrochloric acid, cool to room temperature, product is separated out, and filters, and collects product.Get 2 with recrystallizing methanol, the shallow khaki color crystallization of 6-dihydroxymethyl-4-chlorophenol; Productive rate 51～70%.
The preparation of (2) 2,6-diformyl-4-chlorophenol: with above-mentioned 2,6-dihydroxymethyl-4-chlorophenol and activated manganese dioxide mix with 1: 5～1: 6 mass ratio, add 6～15 times CHCl of reactant total mass
3, reflux and stir 5～10h, to cool off the back suction filtration and remove Manganse Dioxide, decompression is steamed down and is desolventized, and gets the yellow-green colour solid; Use the trichloromethane recrystallization then or with CH
2Cl
2For eluent separates with silica gel column chromatography, obtain 2,6-diformyl-4-chlorophenol.Productive rate is 30～50%.m.p.122～123 ℃.
Intermediate 5-(4-nitro) phenyl-2-benzoyl diazanyl furans is by following prepared:
In p-Nitroaniline, after adding the water stirring of 3～5 times of p-Nitroaniline quality, add the concentrated hydrochloric acid of 2～3 times of p-Nitroaniline quality, be heated to 80～100 ℃ and be back to the p-nitrophenyl amine solvent, be chilled to room temperature under the vigorous stirring, drip chilled NaNO at 0～5 ℃ then
2(concentration is 5mol L to solution
-1, NaNO
2Total amount be 1.5～2.5 times of p-Nitroaniline amount of substance, the control rate of addition adds the back and continues to stir 20～40min, suction filtration, limpid diazonium salt solution (orange).The furancarboxylic acid that takes by weighing 0.5～0.6 times of p-Nitroaniline quality is dissolved in the acetone of 3～4 times of p-Nitroaniline quality, joins in the above-mentioned diazonium salt solution 0.8molL that water that adding p-Nitroaniline quality is 2～3 times and p-Nitroaniline quality are 2～3 times after the cooling
-1CuCl
2Solution.Stir 5～8h under the room temperature, placement is spent the night, leach precipitation, with an amount of massfraction is the dissolving of 1～3% NaOH solution, and the elimination insolubles is 1～2% dilute hydrochloric acid acidifying with massfraction, produce the precipitation of 5-(4-nitrophenyl) furans-2-formic acid, filter, washing obtains 5-(4-nitrophenyl) furans-2-formic acid.Then 5-(4-nitrophenyl) furans-2-formic acid is dissolved in the anhydrous methanol of 10～20 times of its quality, the massfraction that Dropwise 5-(4-nitrophenyl) furans-2-formic acid quality is 1.8～3.6 times is 98% dense H
2SO
4, the 5～8h that refluxes, an amount of anhydrous Na in cooling back
2CO
3Regulate about pH to 7～8, leach solid after, filtrate is the solution of 5-(4-nitrophenyl) furans-2-methyl-formiate.The massfraction that adds 0.75～1.5 times in Dropwise 5-(4-nitrophenyl) furans-2-formic acid quality in this filtrate is 85% hydrazine hydrate, backflow 3～5h, cooling concentrates, separate out solid product, filter and make intermediate 5-(4-nitrophenyl) furans-2-formyl hydrazine.
The sign of the anion receptor compound of we's invention preparation is as follows:
m.p.>300℃，
1H-NMR(DMSO-d
6，400MHz)δ?12.66(s，1H，OH)，12.39(s，2H，NH)，8.75(s，2H，HC＝N)，8.39-7.52(m，14H，ArH).IR(KBr，cm
-1)ν：3417(mb)，3329(w)，3106(w)，1682(m)，1598(s)，1510(s)，1338(s)，1271(m)，1158(w)，852(m).Anal.calced?for?C
30H
19ClN
6O
9：C56.04，H2.98，N13.07；foundC?56.15，H?2.76，N?13.11.
Three, anionic compound in DMSO solution to anionic detection
1, anion receptor compound anionic experiment of colorimetric detection in DMSO solution
Pipette the DMSO solution (2 * 10 of 1mL host compound F3 respectively
-4MolL
-1) in a series of 10mL colorimetric cylinders.Add F respectively
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -DMSO solution (0.01mol/L) 1mL of anionic 4-butyl ammonium is diluted to scale with DMSO, and making various anion concentrations is 50 times of acceptor density, mixes the back and places and spend the night, and surveys its uv-visible absorption spectras (DMSO makes reference) in 25 ℃.3 pairs of each anionic responses of examination compound F 17-hydroxy-corticosterone.
Result: when at the DMSO of anion receptor compound solution (2 * 10
-5MolL
-1) in add F respectively
-, CH
3COO
-And H
2PO
4 -The DMSO solution (50 times of equivalents) of 4-butyl ammonium the time, significant variation has taken place in the DMSO solution colour of anion receptor: become redness from yellow; Simultaneously, as shown in Figure 1, in uv-vis spectra, F
-, CH
3COO
-And H
2PO
4 -Adding make anion receptor DMSO solution respectively 520,480 and the 520nm place corresponding very big absorption peak has appearred, and other anionic adding does not have obvious influence to the DMSO solution colour and the UV spectrum of anion receptor.These phenomenons and presentation of results, anion receptor can colorimetric detection F in DMSO solution
-, CH
3COO
-And H
2PO
4 -Therefore, this compound can be used as colorimetric detection F in DMSO solution
-, CH
3COO
-And H
2PO
4 -Acceptor.
A large amount of experiments show, in concentration 2 * 10
-2～2 * 10
-5MolL
-1The DMSO solution of anion receptor in, add the F that concentration is 1～0.01mol/L respectively
-, CH
3COO
-, H
2PO
4 -The DMSO solution of anionic 4-butyl ammonium mixes the back and placed 0～5 second, and solution colour can both become redness from yellow.
2, the preparation of anion receptor organogel
Organogel is a kind of low-molecular-weight organic compound (gel molecular), supramolecule (soft) material that forms by weak interaction self-assembly between hydrogen bond, Van der Waals force, pi-pi accumulation effect equimolecular in organic solvent.This material has solid material and the distinctive advantage of fluent material simultaneously: gel molecular keeps the chemical property of oneself, can carry out its some reactions in solution; It is stable that this gelatinous material has the solid of being similar to again simultaneously, as be easy to advantage such as preservation.Therefore, if develop anionic colorimetric detection agent based on organogel, solution needs preparation at any time in the time of will avoiding carrying out colorimetric detection with anion receptor solution at present, and the solution for preparing is difficult for preserving and uses shortcoming such as inconvenience.Therefore, we prepare and a kind ofly can be used for the anionic organogel of colorimetric detection on the basis of anion receptor compound.
The preparation method of negatively charged ion organogel of the present invention is: anion receptor is joined among the DMF, be heated to 70～120 ℃ and make its dissolving, the mass percent that forms anion receptor is 0.5～2.0% DMF solution, forms stable anion receptor organogel after being cooled to room temperature.
This organogel has good thermostability, when the boiling point (152 ℃) of DMF, just can become solution state from gel state at leisure.Detect by scanning electron microscope (SEM), find that this organogel exists with three-dimensional netted fiber attitude, sees Fig. 2,3.Can infer that from the structure of anion receptor host compound mainly is self-assembled into organogel by hydrogen bond.
3, the Anion Recognition performance test of anion receptor organogel
On white spot plate, get 9 parts of a spot of negatively charged ion organogels respectively, on these organogels, drip F respectively
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -(concentration is 1～0.001mol/L) to the DMSO solution of anionic 4-butyl ammonium.
Found that the negatively charged ion organogel is when running into the DMSO solution of F-, color becomes orange by yellow; Run into CH
3COO
-DMSO solution the time, color becomes redness by yellow; Run into H
2PO
4 -DMSO solution the time, color becomes safran by yellow; And when containing other anionic solution and running into this gel, the gel color is constant substantially.Therefore, but the F in this negatively charged ion organogel colorimetric detection DMSO solution
-, CH
3COO
-, and H
2PO
4 -
This organogel is as the anionic colorimetric detection agent, have be easy to carry, easy to use, detection sensitivity advantages of higher.
Description of drawings
Fig. 1 is an anion receptor (2 * 10 of the present invention
-4MolL
-1) ultraviolet-visible spectrogram when in DMSO solution, interacting with various negatively charged ion (50 times of equivalents)
Fig. 2 amplifies 20,000 times SEM figure for anion receptor organogel of the present invention
Fig. 3 amplifies 40,000 times SEM figure for anion receptor organogel of the present invention
Embodiment
Synthesizing of embodiment 1, anion receptor compound
(1) intermediate 2,6-diformyl-4-chlorophenol synthetic:
A.2, the preparation of 6-dihydroxymethyl-4-chlorophenol
With 15 gram para-chlorophenols, 7.8 gram Paraformaldehyde 96 and 1.2 gram sodium hydroxide mixtures slowly are heated to 60 ℃, the fusion of 4-chlorophenol, Paraformaldehyde 96 is suspended in wherein, at 60～65 ℃, this reactant is stirred 1h, reaction solution is khaki color and then becomes red-purple, about 65 ℃ this reaction mixture is continued to stir 3.5h, reactant lumps, reaction terminating; The reaction mixture of caking is dissolved in the methyl alcohol of 100mL heat, PH is transferred to about 2～3 with hydrochloric acid; Cool to room temperature separates out 2, and 6-dihydroxymethyl-4-chlorophenol filters, and collects product.Get shallow khaki color crystallization with recrystallizing methanol.Productive rate 65%.
B.2, the preparation of 6-diformyl-4-chlorophenol
In the 500mL reaction flask, add 2 of 3.8 grams (0.02mol), 6-dihydroxymethyl-4-chlorophenol, 25 freshly prepd activated manganese dioxide of gram and 250mLCHCl
3, reflux and stir 6h, to cool off the back suction filtration and remove Manganse Dioxide, decompression is steamed down and is desolventized, and gets the yellow-green colour solid, and silica gel column chromatography separates, and eluent is CH
2Cl
2, obtaining 2,6-diformyl-4-chlorophenol, productive rate are 40%.m.p.122～123 ℃.
(2) intermediate 5-(4-nitro) phenyl-2-benzoyl diazanyl furans is synthetic
Get 8.3g (0.06mol) N-methyl-p-nitroaniline and place the oblique two mouthfuls of bottles of 100mL, add 30mL water and 15mL concentrated hydrochloric acid, reflux is chilled to room temperature to the p-nitrophenyl amine solvent under the vigorous stirring, drips chilled NaNO at 0～5 ℃
2Solution (5.3g NaNO
2+ 15mL water), the control rate of addition adds the back and continues to stir 20 minutes, and suction filtration gets limpid diazonium salt solution (orange).After the furancarboxylic acid that takes by weighing 4.5g (0.04mol) again was dissolved in 30mL acetone, cooling joined in the above-mentioned diazonium salt solution, added 15mL water and (2gCuCl
22H
2O+14mLH
2O), stirred 6 hours under the room temperature, placement is spent the night, and leaches precipitation, with rare NaOH (1%) dissolving, removes insolubles, uses the dilute hydrochloric acid acidifying, obtains p-nitrobenzoic acid.In oblique two mouthfuls of flasks of 250mL, add 5g (0.02mol) p-nitrobenzoic acid and 50mL methyl alcohol and the dense H of 4mL
2SO
4, refluxed 6 hours an amount of anhydrous Na in cooling back under the room temperature
2CO
3Regulate about pH to 7～8, leach solid after, filtrate is the solution of 5-(4-nitrophenyl) furans-2-methyl-formiate.85% of adding 0.025mol hydrazine hydrate in this filtrate, the 3～5h that refluxes, cooling concentrates, and separates out solid product, filters and makes intermediate 5-(4-nitrophenyl) furans-2-formyl hydrazine.
(3) the anion receptor compound is synthetic: respectively with 2 of 5mmol; 6-diformyl-4-chlorophenol and 5-(4-nitro) phenyl-2-benzoyl diazanyl furans places round-bottomed flask; the tosic acid that adds 20mL dehydrated alcohol, 0.01mmol; reflux and stirred 5 hours; decompression steams most of solvent; cooling back suction filtration goes out solid phase prod and is the anion receptor compound, and this compound can be used the DMSO-EtOH recrystallization.
Anion receptor characterizes .m.p.〉300 ℃,
1H-NMR (DMSO-d
6, 400MHz) δ 12.66 (s, 1H, OH), 12.39 (s, 2H, NH), 8.75 (s, 2H, HC=N), 8.39-7.52 (m, 14H, ArH) .IR (KBr, cm
-1) ν: 3417 (mb), 3329 (w), 3106 (w), 1682 (m), 1598 (s), 1510 (s), 1338 (s), 1271 (m), 1158 (w), 852 (m) .Anal.calced for C
30H
19ClN
6O
9: C56.04, H2.98, N13.07; Found C 56.15, H 2.76, N 13.11.
The preparation of embodiment 2, anion receptor organogel
The anion receptor compound of the above-mentioned preparation of 0.015 gram is joined among the 1mL DMF, be heated to 70～120 ℃ and make its dissolving, form mass percent and be 1.5% DMF solution, form stable negatively charged ion organogel after being cooled to room temperature.
Embodiment 3, usefulness anion receptor organogel detect negatively charged ion
Get some parts of a small amount of anion receptor organogels, place on the white spot plate, on organogel, drip F respectively
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -The DMSO solution (0.01mol/L) of anionic 4-butyl ammonium; Organogel becomes orange by yellow, then is F-solution; Organogel becomes redness by yellow, then is CH
3COO
-Solution; Organogel becomes safran by yellow, then is H
2PO
4 -Solution; The organogel nondiscoloration then is other ion solution.
Claims (7)
1, a kind of anion receptor based on nitrofuran formyl hydrazone and phenolic hydroxyl group, its chemical structural formula is as follows:
2; according to claim 1 based on the preparation method of the anion receptor of nitrofuran formyl hydrazone and phenolic hydroxyl group; be with intermediate 2; 6-diformyl-4-chlorophenol and 5-((4-nitro) phenyl-2-benzoyl diazanyl) furans joins in the reactor with the mol ratio of 1:2～2.5; the dehydrated alcohol that adds 10～30 times of reactant total masses is made solvent; the tosic acid of reactant total mass 0.001～0.01% is made catalyzer; in 70～100 ℃ of following stirring and refluxing after 3～8 hours; decompression steams most of solvent; cooling back suction filtration, solid product with dimethyl sulfoxide (DMSO)-ethyl alcohol recrystallization promptly.
3, according to claim 1 based on the anion receptor of nitrofuran formyl hydrazone and phenolic hydroxyl group, conduct is than the acceptor of colour discrimination fluorion, acetate ion and dihydrogen phosphate ions in DMSO solution.
4, as described in the claim 3 based on the anion receptor of nitrofuran formyl hydrazone and phenolic hydroxyl group, in DMSO solution,, be to be 2 * 10 in described anion receptor concentration as method than colour discrimination fluorion, acetate ion and dihydrogen phosphate ions acceptor
-5～2 * 10
-4MolL
-1DMSO solution in, add F respectively
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -Anionic concentration is the DMSO solution of the 4-butyl ammonium of 0.001～0.01mol/L, and with DMSO dilution, making various anionic concentration is 1～50 times of acceptor density, mixes the back and places 0～5 minute; Solution colour becomes redness from yellow, then is F
-, CH
3COO
-, or H
2PO
4 -, nondiscoloration then is other ion solution.
5, according to claim 1 based on the anion receptor of nitrofuran formyl hydrazone and phenolic hydroxyl group, it is characterized in that: adopt following method to be prepared into organogel: anion receptor is joined among the DMF, be heated to 70～120 ℃ and make its dissolving, the mass percent that forms anion receptor is 0.5～2.0% DMF solution, forms stable anion receptor organogel after being cooled to room temperature.
6,, be used for fluorion, acetate and the dihydrogen phosphate ions of colorimetric detection DMSO solution as the anion receptor organogel of method preparation as described in the claim 5.
7, as described in claim 6, there is anion receptor machine gel to be used for the method for fluorion, acetate and the dihydrogen phosphate ions of colorimetric detection DMSO solution, it is characterized in that: the anion receptor organogel of getting nine part of 0.01～0.05 gram respectively, place on the white spot plate, on organogel, drip F respectively
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -Anion concentration is the DMSO solution of the 4-butyl ammonium of 0.001～1mol/L; Organogel becomes orange by yellow, then is F
-Solution; Organogel becomes redness by yellow, then is CH
3COO
-Solution; Organogel becomes safran by yellow, then is H
2PO
4 -Solution; The organogel nondiscoloration then is other ion solution.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942541A (en) * | 2012-12-04 | 2013-02-27 | 西北师范大学 | Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions |
| CN105523979A (en) * | 2015-12-07 | 2016-04-27 | 江汉大学 | Azothiourea anion receptor and preparation method and application thereof |
| CN109540863A (en) * | 2019-01-04 | 2019-03-29 | 中山大学 | A kind of detection method of Nitrofuran antibiotics |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100516038C (en) * | 2006-09-01 | 2009-07-22 | 西北师范大学 | M-benzenedicarbonyl thioureas derivative, preparation and application thereof as fluorinion identification receptor |
| CN101021527B (en) * | 2007-03-12 | 2012-04-11 | 西北师范大学 | Diacyl hydrazones receptor of naked eye detecting F-and its preparation |
-
2008
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942541A (en) * | 2012-12-04 | 2013-02-27 | 西北师范大学 | Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions |
| CN102942541B (en) * | 2012-12-04 | 2014-07-23 | 西北师范大学 | Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions |
| CN105523979A (en) * | 2015-12-07 | 2016-04-27 | 江汉大学 | Azothiourea anion receptor and preparation method and application thereof |
| CN109540863A (en) * | 2019-01-04 | 2019-03-29 | 中山大学 | A kind of detection method of Nitrofuran antibiotics |
| CN109540863B (en) * | 2019-01-04 | 2021-06-15 | 中山大学 | Detection method of nitrofuran antibiotics |
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