CN103570602A - Reagent and method for detecting cyanogen - Google Patents

Reagent and method for detecting cyanogen Download PDF

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CN103570602A
CN103570602A CN201310488125.9A CN201310488125A CN103570602A CN 103570602 A CN103570602 A CN 103570602A CN 201310488125 A CN201310488125 A CN 201310488125A CN 103570602 A CN103570602 A CN 103570602A
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bases
tri
fluorescence
indoles
trimethylammonium
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阴彩霞
霍方俊
杨瑜涛
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Shanxi University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • G01N21/6402—Atomic fluorescence; Laser induced fluorescence
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Abstract

The invention provides a reagent, which is 2, 2', 2''-((1E, 1'E, 1''E)-(hydroxylphenyl-1,3,5-triguaiacyl)tri(ethylene-2,1-2-yl))tri(1,3,3-trimethyl-3H-indole-1-chloride). The reagent is prepared by carrying out reflux on 2-phenol-1,3,5-triformaldehyde and 1-methyl-2,3,3-trimethyl-3H-chloride for 14 hours in ethanol. The raw materials are cheap, reaction conditions are, and easy to produce. A quantitative detection method for cyanogen provided by the invention is implemented by quantitatively detecting the content of cyanogen in DMSO (dimethylsulfoxide) on the basis of 2, 2', 2''-((1E, 1'E, 1''E)-(hydroxylphenyl-1,3,5-triguaiacyl)tri(ethylene-2,1-2-yl))tri(1,3,3-trimethyl-3H-indole-1-chloride). The detection method shows high cyanogen sensitivity and selectivity to cyanogen, is simple, sensitive and rapid in detection process, and obtains accurate detection results.

Description

A kind of reagent and method that detects cyanogen root
Technical field
The present invention relates to cyanogen root detection technique, be specifically related to a kind of reagent and synthetic method thereof, and the application of this reagent in detecting cyanogen root.
Background technology
Cyanogen root can produce severe toxicity to biological organism, if reach 0.5-3.5 mg/kg at the content of human body, can produce fatal effect.Cyanogen root is extremely harmful, can cause vomiting, twitch, and the loss of consciousness, and finally dead.Although it is toxic, prussiate is widely used in gold mining in industry, electroplates protection or decorates, metallurgy, the synthon such as nylon and resin synthetic.Therefore, the method for highly sensitive and highly selective detection cyanogen root has great importance.Up to now, there are various analytical procedures: titration, voltammetry, chromatography, electrochemical appliance, colorimetric estimation and fluorescence.The advantages such as wherein, fluorescent optical sensor is because it has highly sensitive and highly selective, and cost is low, easy detection are especially noticeable.Therefore, we have designed and synthesized a kind of fluorescent probe of new cyanogen root in the present invention, realize highly selective fluoroscopic examination cyanogen root.
Summary of the invention:
The object of this invention is to provide a kind of reagent that synthesizes the detection by quantitative cyanogen root simple, easy to operate, selectivity is high, and the method that detects cyanogen root with this reagent.
Reagent provided by the invention is: 2,2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-), English name is: 2,2', 2''-((1E, 1'E, 1''E)-(2-hydroxybenzene-1,3,5-triyl) tris (ethene-2,1-diyl)) tris (1,3,3-trimethyl-3H-indol-1-ium)
The structural formula of this reagent is:
Figure BDA0000397687700000021
The synthetic method of this reagent, step comprises: by 2-hydroxybenzene-1,3,5-trioxin (2-hydroxybenzene-1,3,5-tricarbaldehyde) with 1-methyl-2,3,3-trimethylammonium-3H-indoles (1-methyl-2,3,3-trimethyl-3H-indolium) 1 ︰ 3 is dissolved in ethanol completely in molar ratio, and mixture refluxes 14 hours, stopped reaction, cooling rear suction filtration, with anhydrous methanol washing, after being dried, the solid that obtains purple is product again.
The method that detects cyanogen root with this reagent, comprises the following steps:
(1), the DMSO solution of this reagent of preparation 2mM;
(2), 1000:1 by volume, the DMSO solution of DMSO and this reagent is added in clean fluorescence cuvette, on Fluorescence spectrophotometer, detect, along with treating adding of test sample, 496nm occurs that fluorescent emission and fluorescence intensity strengthen gradually;
(3), this reagent D MSO solution of the DMSO solution of 2mL, 2 μ L is added in another fluorescence cuvette, respectively when the volume that adds cyanogen root solution is 0.5,1,1.5,2.0,3.0,4.0,8.0 μ L, on Fluorescence spectrophotometer, measuring the fluorescence intensity F that 496nm is corresponding is 31,67,96,132,195,260,535, the cyanogen root concentration of take is X-coordinate, take fluorescence intensity F as ordinate zou drafting figure, obtain the working curve of cyanogen root concentration; Equation of linear regression is: F=66.76c-3.00, and the unit of c is μ M;
(4), HDMSO solution 2000uL and this reagent D MSO solution 2uL are added in clean fluorescence cuvette, with microsyringe, draw V ul testing sample solution, join in this clean fluorescence cuvette, on Fluorescence spectrophotometer, detect, by the equation of linear regression of the fluorescence intensity substitution step (3) recording, obtain concentration c, testing sample C treat test sample=2000uL * c * 10 -6/ VuL, can try to achieve the concentration of cyanogen root.
Compared with prior art, tool of the present invention has the following advantages and effect:
1, detection system is with low cost, and reagent is by 2-hydroxybenzene-1,3,5-trioxin and 1-methyl-2, and 3,3-trimethylammonium-3H-indoles single step reaction makes;
2, detection method of the present invention, has shown high susceptibility and selectivity to cyanogen root;
3, detection means is simple, only need to can realize by Fluorescence spectrophotometer.
Accompanying drawing explanation:
The nuclear-magnetism H spectrum of the reagent of Fig. 1 embodiment 1 preparation
The nuclear-magnetism C spectrum of the reagent of Fig. 2 embodiment 1 preparation
The mass spectrum of the reagent of Fig. 3 embodiment 1 preparation
The fluorescent emission figure of Fig. 4 embodiment 2 reagent and the effect of cyanogen root
The fluorescence histogram of Fig. 5 embodiment 3 reagent and various analytes
Fig. 6 embodiment 4 measures the working curve of cyanogen root
The fluorescent emission figure of Fig. 7 embodiment 5 working samples
Embodiment:
Embodiment 1
Reagent preparation:
By 0.178g, 2-hydroxybenzene-1,3,5-trioxin and 0.903g, 1-methyl-2,3,3-trimethylammonium-3H-indoles is dissolved in 20mL ethanol completely, and mixture refluxes 14 hours, stopped reaction, cooling rear suction filtration, then wash with anhydrous methanol 10mL, after being dried, the solid that obtains purple is this reagent.
Reagent characterizes:
1h NMR (300MHz, 25 ℃, DMSO-d 6): δ 8.66 (s, Ar-H), 8.43 (d, C=C-H, 1H; J=15.4), 8.38 (m, Ar-H, 1H, J=24.6); 8.78 (m, Ar-H, 3H, J=36.9); 7.6 (m, Ar-H, 3H, J=30.4) 7.5 (d; C=C-H, 1H, J=16,1); 4.15 (s, 3H), 1.79 (s, 6H) are (Fig. 1); 13c NMR (75MHz, DMSO-d 6): δ 181.1,179.1,150.7,142.6,141.6,128.5,128.1,126.8,122.4,114.1,51.0,50.6,26.1,25.1(Fig. 2); ESI-MS m/2z323.00(Fig. 3); Elemental analysis (calcd.%) for C 45h 48i 3n 3o:C, 52.60; H, 4.71; N, 4.09; Found:C, 52.66; H, 4.68; N, 4.04.
Embodiment 2
With 2 of DMSO preparation 2mM, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) solution; 2 of the DMSO solution of 2mL and 2 μ L, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) DMSO solution is added in clean fluorescence cuvette, get the solution of cyanogen root, be added in this cuvette gradually with microsyringe, application of sample limit, limit is detected on Fluorescence spectrophotometer, along with adding of cyanogen root, 496nm place occurs that fluorescent emission and fluorescence intensity strengthen gradually.Fluorescent emission figure is shown in Fig. 4.
Embodiment 3
With 2 of DMSO preparation 2mM, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) solution; In 16 fluorescence cuvettes, respectively add 2 of the DMSO solution of 2mL and 2.0 μ L, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) DMSO solution, the cyanogen root that adds respectively again 4 molar equivalents, and the various analytes of 50 molar equivalents: F -, Cl -, Br -, NO 3 -, HSO 3 -, SCN -, S 2o 3 2-, AcO -, CO 3 2-, ClO 4 -, HS -, SO 4 2-, HCO 3 -, Cys detects on Fluorescence spectrophotometer, draws the histogram of the 496nm relative intensity of fluorescence that different analytes are corresponding, (see figure 5).Cyanogen root makes 2,2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) fluorescence intensity is increased to 535 by nothing, and other analyte does not cause 2 substantially, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) variation of three (1,3,3-trimethylammonium-3H-indoles-1-) fluorescence intensity.
The experiment proved that, other analyte is the mensuration of interference system to cyanogen root not.
Embodiment 4
The DMSO solution of 2mL, 2 of 2 μ L, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1, 3, 5-tri-bases) three (ethene-2, 1-bis-bases)) three (1, 3, 3-trimethylammonium-3H-indoles-1-) DMSO solution is added in another fluorescence cuvette, at the volume that adds cyanogen root solution, be 0.5 respectively, 1, 1.5, 2.0, 3.0, 4.0, during 8.0 μ L, on Fluorescence spectrophotometer, measuring the fluorescence intensity F that 496nm is corresponding is 31, 67, 96, 132, 195, 260, 535, the cyanogen root concentration of take is X-coordinate, take fluorescence intensity F as ordinate zou drafting figure, obtain the working curve of cyanogen root concentration, equation of linear regression is: F=66.76c-3.00, the unit of c is μ M.See Fig. 6.
Embodiment 5
With 2 of DMSO preparation 2mM, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) solution; 2 of the DMSO solution of 2mL and 2.0 μ L, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) DMSO solution is added in clean fluorescence cuvette, the solution 6.0 μ L that get cyanogen root, are added in this cuvette with microsyringe, and the corresponding fluorescence intensity F that measures 496nm simultaneously in fluorescence spectrophotometer is 397, by the equation of linear regression of embodiment 3, try to achieve c=5.99 * 10 -6mol/L, deviation is 0.99%, sees Fig. 7.

Claims (3)

1. a reagent, is characterized in that, it is 2,2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-), and structural formula is:
Figure FDA0000397687690000011
2. the synthetic method of a kind of reagent as claimed in claim 1, it is characterized in that step is: by 2-hydroxybenzene-1,3,5-trioxin and 1-methyl-2,3,3-trimethylammonium-3H-indoles in molar ratio 1 ︰ 3 is dissolved in ethanol completely, and mixture refluxes 14 hours, stopped reaction, cooling rear suction filtration, with anhydrous methanol washing, after being dried, obtain the solid of purple again.
3. a method that detects cyanogen root: it is characterized in that, step is:
(1), prepare 2 of 2mM, 2', the DMSO solution of 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-);
(2), 1000:1 by volume, DMSO solution and 2,2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) DMSO solution is added in clean fluorescence cuvette, on Fluorescence spectrophotometer, detect, along with treating adding of test sample, 496nm occurs that fluorescent emission and fluorescence intensity strengthen gradually;
(3), the DMSO solution of 2mL, 2 of 2 μ L, 2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1, 3, 5-tri-bases) three (ethene-2, 1-bis-bases)) three (1, 3, 3-trimethylammonium-3H-indoles-1-) DMSO solution is added in another fluorescence cuvette, at the volume that adds cyanogen root solution, be 0.5 respectively, 1, 1.5, 2.0, 3.0, 4.0, during 8.0 μ L, on Fluorescence spectrophotometer, measuring the fluorescence intensity F that 496nm is corresponding is 31, 67, 96, 132, 195, 260, 535, the cyanogen root concentration of take is X-coordinate, take fluorescence intensity F as ordinate zou drafting figure, obtain the working curve of cyanogen root concentration, equation of linear regression is: F=66.76c-3.00, and the unit of c is μ M,
(4), by DMSO solution 2000uL and 2,2', 2''-((1E, 1'E, 1''E)-(hydroxy phenyl-1,3,5-, tri-bases) three (ethene-2,1-bis-bases)) three (1,3,3-trimethylammonium-3H-indoles-1-) DMSO solution 2uL is added in clean fluorescence cuvette, with microsyringe, draws V ul testing sample solution, joins in this clean fluorescence cuvette, on Fluorescence spectrophotometer, detect, equation of linear regression by the fluorescence intensity substitution step (3) recording, obtains concentration c, testing sample C treat test sample=2000uL * c * 10 -6/ VuL, can try to achieve the concentration of cyanogen root.
CN201310488125.9A 2013-10-18 2013-10-18 Reagent and method for detecting cyanogen Pending CN103570602A (en)

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Publication number Priority date Publication date Assignee Title
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CN105777607A (en) * 2016-04-22 2016-07-20 山西大学 Triphenylamine bis-indolyl iodised salt as well as synthesis method and application thereof
CN109053778A (en) * 2018-06-14 2018-12-21 忻州师范学院 The reagent and its synthetic method of specific detection cyanogen root and application

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105181684A (en) * 2015-07-16 2015-12-23 西南大学 Monomolecular-layer probe for detecting cyanide ion and preparation and application methods thereof
CN105181684B (en) * 2015-07-16 2018-03-30 西南大学 A kind of monolayer probe and its methods for making and using same for detecting cyanide ion
CN105777607A (en) * 2016-04-22 2016-07-20 山西大学 Triphenylamine bis-indolyl iodised salt as well as synthesis method and application thereof
CN105777607B (en) * 2016-04-22 2019-04-02 山西大学 A kind of double indoles salt compounded of iodine of triphenylamine and its synthetic method and application
CN109053778A (en) * 2018-06-14 2018-12-21 忻州师范学院 The reagent and its synthetic method of specific detection cyanogen root and application

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Application publication date: 20140212