CN110317158A - A kind of synthesis of double-mode optical probe indoles iodide and its detection to uns-dimethylhydrazine - Google Patents
A kind of synthesis of double-mode optical probe indoles iodide and its detection to uns-dimethylhydrazine Download PDFInfo
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- CN110317158A CN110317158A CN201910504037.0A CN201910504037A CN110317158A CN 110317158 A CN110317158 A CN 110317158A CN 201910504037 A CN201910504037 A CN 201910504037A CN 110317158 A CN110317158 A CN 110317158A
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- indoles
- iodide
- trimethyl
- acetoxy
- dimethylhydrazine
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- 239000000523 sample Substances 0.000 title claims abstract description 73
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 230000003287 optical effect Effects 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- -1 indoles iodide Chemical class 0.000 title claims description 5
- 238000001514 detection method Methods 0.000 title abstract description 20
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 claims abstract description 51
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000002189 fluorescence spectrum Methods 0.000 claims description 17
- 238000000862 absorption spectrum Methods 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 13
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229960001866 silicon dioxide Drugs 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 239000002351 wastewater Substances 0.000 claims description 3
- 238000000295 emission spectrum Methods 0.000 claims description 2
- 238000004445 quantitative analysis Methods 0.000 claims description 2
- 239000011550 stock solution Substances 0.000 claims 2
- 238000011088 calibration curve Methods 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 238000001228 spectrum Methods 0.000 abstract description 2
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 abstract 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000012447 hatching Effects 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical class C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003950 pathogenic mechanism Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000012247 sodium ferrocyanide Nutrition 0.000 description 1
- 239000000264 sodium ferrocyanide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
Classifications
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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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the 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
- G01N2021/6417—Spectrofluorimetric devices
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- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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- Optics & Photonics (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
The present invention relates to a kind of optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide, its synthesis and its detections to uns-dimethylhydrazine.For the optical probe with -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4-Vinyl phenol base) for fluorogen, acetyl group is recognition group, has synthesized uns-dimethylhydrazine ((CH3)2NNH2) optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide.When there are when uns-dimethylhydrazine in sample, uns-dimethylhydrazine can affine attack probe carbonyl, electronics above ketonic oxygen is set to occur to shift and leave away to generate acethydrazide, release fluorogen, fluorescence is set to restore, uns-dimethylhydrazine is detected using the variation of fluorescence signal, the range of linearity is 0-300 μ g/L, and detection is limited to 2.4 μ g/L.Meanwhile the process is accompanied by solution by the light yellow color change to pink colour, accordingly it is also possible to which the variation using ultraviolet-visible light spectrum signal is measured uns-dimethylhydrazine.
Description
The synthesis of probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide and its right
The detection of uns-dimethylhydrazine.
Technical field
The present invention relates to probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodate
The synthesis of object and its detection to uns-dimethylhydrazine, belong to luminous organic material field.
Technical background
Uns-dimethylhydrazine (UDMH)/dinitrogen tetroxide (N2O4) double elements liquid propellant is high with energy, specific impulse is big, can be normal
The features such as temperature storage, be the main fuel of the emission tests such as China's guided missile, satellite, airship and carrier rocket, but it is to environment
Pollution cannot but despise.Uns-dimethylhydrazine miscible with water can generate corresponding waste water, as environment enters ecological recycle system,
Injury in varying degrees can be all caused to the central nervous system of human body, kidney, liver etc., pathogenic mechanism is due to hydrazine
The intrusion of substance causes the intracorporal vitamin B of people6It is independent shortage and caused by.Uns-dimethylhydrazine is to people's body in order to prevent
The ecological environments such as atmosphere, water body and the soil on health and periphery cause damages, limitation of the countries in the world to uns-dimethylhydrazine in environment
Value has stringent regulation, therefore, establishes method that is simple, quickly, sensitively detecting uns-dimethylhydrazine and is of great significance.
The detection method for the uns-dimethylhydrazine reported at present mainly has: amino sodium ferrocyanide spectrophotometry, electrochemistry
Method, chromatography, chemoluminescence method and chemical analysis etc. solve the detection of uns-dimethylhydrazine in these methods to varying degrees
Problem, but also detection sensitivity, operating condition it is cumbersome or instrument in terms of be respectively present different defects.Base
In this, the present invention establishes a kind of simple, quick, selective good and high sensitivity fluorophotometric analysis method, to ambient water
Uns-dimethylhydrazine in sample is monitored, and is reached control environmental pollution and is ensured national defence or space flight related fields operator's health
Purpose.
Summary of the invention
In view of above-mentioned, the purpose of the present invention is: a kind of double-mode optical probe 2- (4- acetoxy-styrene base) -1,3,
The synthesis of 3- trimethyl -3H- indoles -1- iodide and its detection to uns-dimethylhydrazine.
The purpose of the present invention is be achieved through the following technical solutions:
The synthesis of probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide:
A. by 1,2,3,3- tetramethyl -3H- indoles iodide (903.5mg, 3.0mmol), parahydroxyben-zaldehyde (439.6mg,
3.6 mmol) mixing is placed in 100mL and contains in the round-bottomed flask of 40mL dehydrated alcohol, after being heated to reflux 12h, pass through thin-layer chromatography
(TLC) it monitors, filters after the reaction was completed, and with petroleum ether to no parahydroxyben-zaldehyde, product is in 60 DEG C of vacuum drying, nothing
It need to be further purified, obtain -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4-Vinyl phenol base)；
B. 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide (80.8mg, 0.2mmol) are dissolved
In 20 mL CH2Cl2In, triethylamine (Et is added3N, 45 μ L, 0.32mmol), it is stirred at 0 DEG C, and acetyl bromide is added
(C2H3BrO, 30 μ L, 0.4mmol), it is concentrated under reduced pressure after reacting 10min, through silicagel column (CH2Cl2/CH3OH=90:1) it purifies
To probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide.
The composite structure formula of probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
It is as follows:
Advantages of the present invention and generate the utility model has the advantages that
The present invention overcomes in place of the deficiencies in the prior art.Utilize 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- Yin
Diindyl -1- iodide and acetyl bromide have synthesized a kind of double-mode optical probe 2- (4- acetoxy-styrene base) -1,3,3- front threes
Base -3H- indoles -1- iodide.Probe and (CH3)2NNH22- (4-Vinyl phenol base) -1,3,3- trimethyl-is generated after reaction
3H- indoles -1- iodide, UV absorption wavelength by 385nm red shift to 530nm, fluorescent emission at 553nm with
(CH3)2NNH2The increase of concentration and enhance.The present invention is for (CH in wastewater sample3)2NNH2The measurement of content is sent out based on fluorescence
Penetrate intensity and (CH3)2NNH2Concentration and ultraviolet absorptivity ratio (λ530/λ385) with the linear relationship of uns-dimethylhydrazine concentration, calculate most
Low detection limit is respectively 2.5 μ g/L and 8.4 μ g/L, lower than China to Drinking Water and " missile propellant Sewage Water Emissions
Standard " defined 0.1mg/L and 0.5mg/L Limited Doses, can to the safety of detected environment carry out rational evaluation.This hair
Double-mode optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodate object light of bright synthesis
It learns property to stablize, specific good, high sensitivity, is a kind of method for efficiently detecting uns-dimethylhydrazine.
Detailed description of the invention
Fig. 1 is synthesized 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide in DMSO-
d6In1H NMR spectra.
Fig. 2 is synthesized 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide in DMSO-
d6In13C NMR spectra.
Fig. 3 is synthesized probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
In DMSO-d6In1H NMR spectra
Fig. 4 is that synthesized probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide exist
DMSO-d6In13C NMR spectra
Fig. 5 is synthesized probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
HRMS spectrogram, 320.1652 [M+H in spectrogram+] it is probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- Yin
The molecular ion peak of diindyl -1- iodide.
Fig. 6 be probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide (20 μM) with
(200 μM) of uns-dimethylhydrazine reaction before (solid line) and after (dotted line) ultra-violet absorption spectrum (A) and fluorescence emission spectrum (B).
Fig. 7 is probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide (20 μM)
The fluorescence spectrum reacted with uns-dimethylhydrazine (12 μ g/L) or other chaff interferents；
Fig. 8 is probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide (20 μM) and inclined two
Methylhydrazine and other chaff interferents coexist in the case where fluorescence intensity change.
Fig. 9 is probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide (20 μM)
Change (A) and fluorescence intensity (λ with the fluorescence spectrum after the uns-dimethylhydrazine effect of various concentrationem=553nm) and uns-dimethylhydrazine
The linear relationship of concentration.
Figure 10 is probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide (20 μM)
With after the effect of the uns-dimethylhydrazine of various concentration uv-visible absorption spectra variation (A) and with the uns-dimethylhydrazine of various concentration
Ultraviolet absorptivity ratio (λ after effect530/λ385) with the linear relationship of uns-dimethylhydrazine concentration.
Specific embodiment
Technical solution of the present invention is described further again with reference to the accompanying drawings and examples:
Embodiment 1
By 1,2,3,3- tetramethyl -3H- indoles iodide (903.5mg, 3.0mmol), and parahydroxyben-zaldehyde (439.6mg, 3.6
Mmol) mixing is placed in 100mL and contains in the round-bottomed flask of 40mL dehydrated alcohol, after being heated to reflux 12h, passes through thin-layer chromatography
(TLC) it monitors, filters after the reaction was completed, and with petroleum ether to no parahydroxyben-zaldehyde, product is in 60 DEG C of vacuum drying, nothing
It need to be further purified, obtain -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4-Vinyl phenol base), as anti-in next step
The reactant answered；
Compound-(4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide (80.8mg, 0.2mmol) are molten
Solution is in 20mL CH2Cl2In, triethylamine (Et is added3N, 45 μ L, 0.32mmol), it is stirred at 0 DEG C, and acetyl bromide is added
(C2H3BrO, 30 μ L, 0.4mmol), it is concentrated under reduced pressure after reacting 10min, through silicagel column (CH2Cl2/CH3OH=90:1) it purifies
To optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide.
Parallel probe 2- (4- acetoxy-styrene the base) -1,3,3- trimethyl -3H- Yin for preparing 6 concentration and being 20 μM
Diindyl -1- iodide solution, is separately added into the uns-dimethylhydrazine standard solution containing various concentration thereto, after 20min, measures respectively
The fluorescence spectra and UV-visible absorption spectrum of above-mentioned solution record fluorescent emission intensity and uv-visible absorption spectra
The variation of absorbance, according to fluorescence intensity level (Iλem=553nm) with the relationship and ultraviolet-ray visible absorbing light of uns-dimethylhydrazine concentration
Compose absorbance ratio (Aλ530/Aλ385) with the relationship of uns-dimethylhydrazine concentration draw standard curve.
Probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodine that compound concentration is 20 μM
Compound solution, is added sample solution thereto, after 20min, measures its fluorescence spectra and UV-visible absorption spectrum, remembers
The variation for recording fluorescent emission intensity and uv-visible absorption spectra absorbance calculates inclined two in sample according to above-mentioned standard curve
The concentration of methylhydrazine.
Product is tested with nuclear magnetic resonance chemical analyser after probe synthesis, obtains its hydrogen spectrogram 1, chemical shift data
Are as follows:1H NMR(400MHz,DMSO-d6) δ=8.21 (dd, J=12.4,8.4Hz, 3H), 7.76 (d, J=16.2Hz, 1H),
7.67 (dd, J=5.9,3.0Hz, 1H), 7.62-7.56 (m, 3H), 7.29 (d, J=8.7Hz, 2H), 4.46 (s, 3H), 2.33
(s,3H), 1.87(s,6H).
Obtain its carbon spectrogram 2, chemical shift data are as follows:
13C NMR(101MHz,DMSO-d6) δ=181.87,168.84,154.03,151.76,143.61,141.79,
132.11, 131.86,129.47,128.95,122.81,115.31,113.29,52.26,45.67,34.72,25.64,
25.18,20.94.
High resolution mass spectrum Fig. 3 shows that its molecular weight is ESI-MS m/z (M+H+)=320.1652.
The above characterization demonstrates probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodate
The synthesis success of object.
Embodiment 2
1. spectrum experiment
Measurement compound 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide and probe 2- (4- first
Acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide uv-visible absorption spectra and fluorescent emission
Spectrum.As shown in Fig. 6, -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4- acetoxy-styrene base) itself exist
Strong absorption band is shown at 385nm, after reacting 20min with uns-dimethylhydrazine, the absorption band at 385nm fades away, while
Occurs new absorption peak at 530nm, simultaneous solution colour illustrates uns-dimethylhydrazine and 2- by the yellowish variation to pink
The novel substance that the reaction of (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide generates has and probe
Different spectral properties.In addition, carrying out fluorescence spectrometry to probe solution, the Ke Yi when 520nm is excited is found
Apparent enhancing fluorescence signal (Fig. 6-B) is observed at 553nm.Above-mentioned probe reacts front and back uv-vis spectra with uns-dimethylhydrazine
Variation with fluorescent spectroscopic properties, which can be used in, carries out double mode detection to the content of uns-dimethylhydrazine in sample.
2. selectivity experiment
In order to verify probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide to inclined diformazan
The selectivity of hydrazine detection, the present invention is by -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4- acetoxy-styrene base)
(20 μM) and other possible interference components (20 μ g/L, Cys, GSH, Gln, hydroxylamine, urea, aniline,
Thiourea, K+, Ca2+, Na+, Mg2+, Cu2+, Zn2+, Al3+, Fe3+, Hg+, F-, Br-, Cl-, I-, ClO4 -, Ac-, CO3 2-,
H2PO4 -) hatching 20min, after the completion of hatching, probe is recorded respectively with ultraviolet-visible spectrophotometer and sepectrophotofluorometer
The uv-visible absorption spectra of 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide and
Fluorescence emission spectrum under 520 nm excitation wavelengths.As shown in fig. 7, working as probe 2- (4- acetoxy-styrene base) -1,3,3-
After trimethyl -3H- indoles -1- iodide and uns-dimethylhydrazine effect, the fluorescent emission intensity at 553nm significantly increases (λex
=520nm), and with after the effect of other analytes, ultraviolet and fluorescence spectrum is unchanged.Meanwhile in uns-dimethylhydrazine and its
Under his chaff interferent Coexistence Situation, -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4- acetoxy-styrene base) are still right
(CH3)2NNH2With good recognition reaction (as shown in Figure 8).This is the results show that 2- (4- acetoxy-styrene base)-
1,3,3- trimethyl -3H- indoles -1- iodide can realize the identification of specificity to uns-dimethylhydrazine.
3. concentration titrations are tested
It can be to inclined diformazan based on probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
Hydrazine carries out the feature of specific recognition, and the present invention has studied probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyls -
Quantitative detection ability of the 3H- indoles -1- iodide for uns-dimethylhydrazine.The present invention uses UV absorption and fluorescence emission spectrum respectively
Both of which quantitative can be carried out investigation to its.20 μ L 1mmol/L probe 2- (4- acetoxy-styrene base) -1,3,3-
Trimethyl -3H- indoles -1- iodide are mixed with 280 μ L DMAO, and the uns-dimethylhydrazine that 60 μ g/L of different volumes are added is molten
Liquid is settled to 1mL with the PBS of 10mM, after hatching 20min, uses sepectrophotofluorometer and spectrophotometry respectively
Meter record probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide and its and uns-dimethylhydrazine
The fluorescence emission spectrum and ultra-violet absorption spectrum of product after reaction.Its fluorescence emission spectrum is with inclined it can be seen from Fig. 9-A
The increase of Dimethylhydrazine concentration, -1,3,3- trimethyl -3H- indoles -1- iodide molecules of 2- (4- acetoxy-styrene base) exist
Fluorescent emission at 553nm gradually increases, and its emissive porwer and uns-dimethylhydrazine concentration (0-300 μ g/L) presentation are good linear
Relationship, detection limit (LOD, S/N=3) can achieve 2.5 μ g/L (Fig. 9-B).Illustrate probe 2- (4- acetoxy-styrene
Base) -1,3,3- trimethyl -3H- indoles -1- iodide can using Fluorescence Spectrometer to uns-dimethylhydrazine carry out quantitative analysis.
In addition, with the increase of uns-dimethylhydrazine additional amount, 2- (4- acetoxy-styrene base) it can be seen from Figure 10-A
UV absorption of -1,3, the 3- trimethyl -3H- indoles -1- iodide at 385nm gradually decreases, and occurs newly at 530nm
It absorption peak and gradually increases, absorbance ratio (Aλ530/Aλ385) and uns-dimethylhydrazine presented in the concentration range of 0-600 μ g/L
Good linear relationship, detection limit (LOD, S/N=3) can achieve 8.4 μ g/L (Figure 10-B).It is above-mentioned statistics indicate that being invented
Probe can carry out quantitative detection to uns-dimethylhydrazine under fluorescence spectrum and uv-visible absorption spectra both of which.
4. the measurement of uns-dimethylhydrazine content in Huanghe water
In order to verify probe in actual sample to the applicability of uns-dimethylhydrazine detection, the present invention is determined inclined two in Yellow River water samples
The content of methylhydrazine and recovery testu is carried out.Experiment measures recovery of standard addition such as 1 institute of table of uns-dimethylhydrazine in Yellow River water samples
Show, data illustrate that -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4- acetoxy-styrene base) can be applied in table
The detection of uns-dimethylhydrazine in actual sample.
Method particularly includes:
A. sample treatment
Yellow River water samples are derived from Lanzhou Huanghe section, 0.45 μm of filtering with microporous membrane of acquired water sample.
B. in fluorescence spectrum method for measuring actual sample uns-dimethylhydrazine content
The above-mentioned actual sample handled well of 700 μ L is taken, 20 μ L1mmol/L probe 2- (4- acetoxy-styrene base) are separately added into
- 1,3,3- trimethyl -3H- indoles -1- iodide solutions and 280 μ L DMSO, shake up, incubation at room temperature 20min uses fluorescence spectrophotometer
Photometer records the fluorescence emission spectrum under the excitation wavelength of 520nm.In addition, a certain amount of inclined diformazan is added in actual sample
Hydrazine standard solution is detected after constant volume by aforesaid operations, corresponding recovery of standard addition is calculated.Table 1 is in Yellow River water samples
Uns-dimethylhydrazine recovery of standard addition experimental data.
1 2- of table (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide are in actual sample
Uns-dimethylhydrazine measurement and recovery of standard addition
By to probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide and its with inclined two
The optical Quality Research in methylhydrazine reaction front and back, it was demonstrated that the molecular probe 2- (4- acetoxy-styrene base) -1 that the present invention synthesizes,
3,3- trimethyl -3H- indoles -1- iodide can be realized by fluorescence emission spectrum and uv-visible absorption spectra to inclined two
The measurement of methylhydrazine, compared to traditional detection method, optical property of the present invention is stablized, and specificity is good, and high sensitivity, probe is easier to
It saves, operation is simpler, is a kind of short-cut method for efficiently detecting uns-dimethylhydrazine.
Claims (3)
1. probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide of formula (I)
Probe 2- described in claim 1 2. (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
Synthesis, the steps include:
A. by 1,2,3,3- tetramethyl -3H- indoles iodide (903.5mg, 3.0mmol), parahydroxyben-zaldehyde (439.6mg,
3.6mmol) mixing is placed in 100mL and contains in the round-bottomed flask of 40mL dehydrated alcohol, after being heated to reflux 12h, passes through thin-layer chromatography
(TLC) it monitors, filters after the reaction was completed, and with petroleum ether to no parahydroxyben-zaldehyde, product is in 60 DEG C of vacuum drying, nothing
It need to be further purified, obtain -1,3,3- trimethyl -3H- indoles -1- iodide of 2- (4-Vinyl phenol base)；
B. 2- (4-Vinyl phenol base) -1,3,3- trimethyl -3H- indoles -1- iodide (80.8mg, 0.2mmol) are dissolved
In 20mL CH2Cl2In, triethylamine (Et is added3N, 45 μ L, 0.32mmol), it is stirred at 0 DEG C, and acetyl bromide is added
(C2H3BrO, 30 μ L, 0.4mmol), it is concentrated under reduced pressure after reacting 10min, through silicagel column (CH2Cl2/CH3OH=90:1) purifying obtains
Optical probe -2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide.
3. probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide described in claim 1
Detect uns-dimethylhydrazine ((CH3)2NNH2), it the steps include:
A. 2.2mg probe is accurately weighed, 5.0mL is dissolved and be settled to DMSO, obtains the probe stock solution of 1mmol/L, then take
280 μ L DMSO are added in the probe stock solution of 20 μ L1mmol/L, are diluted to 1.0mL with the PBS of 10mM caching solution, use is ultraviolet
Absorption spectrometer and Fluorescence Spectrometer measure optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- respectively
The Absorption and emission spectra of indoles -1- iodide, after measured, UV absorption maximum wavelength are to have at 553nm at 385nm
Faint fluorescent emission；(CH is added thereto3)2NNH2, after 20min, generate 2- (4-Vinyl phenol base) -1,3,3- front threes
Base -3H- indoles -1- iodide, from 385nm red shift to 530nm, the transmitting of most hyperfluorescence exists UV absorption maximum wavelength
At 553nm, while also along with solution colour by the faint yellow variation to pink colour, optical probe 2- (4- acetoxy-styrene
Base) -1,3,3- trimethyl -3H- indoles -1- iodide can be right under ultraviolet-ray visible absorbing and fluorescent emission both of which
(CH3)2NNH2Carry out quantitative analysis；
B. 20 μ are configured by optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
(the CH that concentration is 0-500 μM is added in the solution of M thereto3)2NNH2, after 20min, 2- (4-Vinyl phenol base) -1 is generated,
3,3- trimethyl -3H- indoles -1- iodide are observed its color change, while being examined with ultra-violet absorption spectrum and fluorescence emission spectrum
It surveys, its ultraviolet absorptivity ratio at 530nm and 385nm and the fluorescent emission intensity at 553nm is recorded, according to (CH3)2NNH2Concentration and fluorescence emission spectrum intensity and ultra-violet absorption spectrum dulling luminosity ratio (λ530/λ385) standard song is established respectively
Line；
C. 20 μ are configured by optical probe 2- (4- acetoxy-styrene base) -1,3,3- trimethyl -3H- indoles -1- iodide
The solution of M is added contains (CH thereto3)2NNH2Wastewater sample, after 20min, generate 2- (4-Vinyl phenol base) -1,3,
3- trimethyl -3H- indoles -1- iodide are observed its color change, while being detected with fluorescence emission spectrum and ultra-violet absorption spectrum
Contain (CH3)2NNH2Water sample, and according to calibration curve equation calculate sample in (CH3)2NNH2Content.
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| CN113563354A (en) * | 2021-08-26 | 2021-10-29 | 南京林业大学 | Difunctional fluorescent probe for detecting alkaline pH and/or viscosity and preparation method and application thereof |
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