CN108918495A - The method of spectrophotometry quantitative detection cyanide ion based on 2- aldehyde radical rhodamine derivative - Google Patents
The method of spectrophotometry quantitative detection cyanide ion based on 2- aldehyde radical rhodamine derivative Download PDFInfo
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002798 spectrophotometry method Methods 0.000 title claims abstract description 26
- 238000001514 detection method Methods 0.000 title abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000007853 buffer solution Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 20
- 235000019441 ethanol Nutrition 0.000 claims abstract description 16
- 238000002835 absorbance Methods 0.000 claims abstract description 11
- LEAHFJQFYSDGGP-UHFFFAOYSA-K trisodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[Na+].OP(O)([O-])=O.OP([O-])([O-])=O LEAHFJQFYSDGGP-UHFFFAOYSA-K 0.000 claims abstract description 11
- 238000010521 absorption reaction Methods 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- -1 rhodamine compound Chemical class 0.000 claims description 21
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 238000004440 column chromatography Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- 230000000171 quenching effect Effects 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000008055 phosphate buffer solution Substances 0.000 claims description 7
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 claims description 5
- MUSLHCJRTRQOSP-UHFFFAOYSA-N rhodamine 101 Chemical compound [O-]C(=O)C1=CC=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MUSLHCJRTRQOSP-UHFFFAOYSA-N 0.000 claims description 5
- MYIOYATURDILJN-UHFFFAOYSA-N rhodamine 110 Chemical compound [Cl-].C=12C=CC(N)=CC2=[O+]C2=CC(N)=CC=C2C=1C1=CC=CC=C1C(O)=O MYIOYATURDILJN-UHFFFAOYSA-N 0.000 claims description 5
- 229940043267 rhodamine b Drugs 0.000 claims description 5
- WGTODYJZXSJIAG-UHFFFAOYSA-N tetramethylrhodamine chloride Chemical compound [Cl-].C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C(O)=O WGTODYJZXSJIAG-UHFFFAOYSA-N 0.000 claims description 5
- QYOUEYXPOYMCDV-UHFFFAOYSA-N C(C)O[AlH]OCC.[Li] Chemical compound C(C)O[AlH]OCC.[Li] QYOUEYXPOYMCDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000085 borane Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007850 fluorescent dye Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 231100000570 acute poisoning Toxicity 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- OKGGRXMKBJLXHI-UHFFFAOYSA-N lithium;triethoxyalumane Chemical compound [Li].CCO[Al](OCC)OCC OKGGRXMKBJLXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000004557 single molecule detection Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Abstract
The present invention relates to the methods of the spectrophotometry quantitative detection cyanide ion based on 2- aldehyde radical rhodamine derivative.It is added to the solution to be measured containing cyanide ion in the buffer solution of 2- aldehyde radical rhodamine derivative, is uniformly mixed, under spectrophotometer, measures the absorbance at maximum absorption band.The buffer solution of the 2- aldehyde radical rhodamine derivative is in 2- aldehyde radical rhodamine derivative, to sequentially add ethyl alcohol, disodium hydrogen phosphate-sodium dihydrogen phosphate buffer, is uniformly mixed and is made.Cyanide ion can fast and accurately be measured using method of the invention.
Description
Technical Field
The invention belongs to the field of chemical analysis, and particularly relates to a method for rapidly detecting cyanide by using a colorless rhodamine leuco body generated by the reaction of a 2-aldehyde rhodamine derivative and cyanide.
Background
Cyanide is a highly toxic substance and can be divided into simple cyanide and complex cyanide, the toxicity of the cyanide is the greatest of cyanide ions, the cyanide is combined with human ferricytochrome oxidase to generate ferricytochrome oxidase cyanide and lose the effect of oxygen transfer, and hypoxia asphyxia is caused, and in addition, the cyanide also has great toxicity to aquatic organisms. At present, cyanides in the environment mainly come from electroplating wastewater, coal gas washing water of a coke oven and a blast furnace, and various industrial wastewater of synthetic ammonia, non-ferrous metal ore dressing, smelting, chemical fiber production, pharmacy and the like. The water contains 0.1mg/L cyanide to kill insects, 0.3mg/L cyanide to kill self-cleaning microbes, and 0.3-0.5 mg/L cyanide to kill fish. Human beings can kill the disease only by taking about 0.28g of potassium cyanide orally. Cyanide is extremely harmful and can produce toxic symptoms within seconds. After the cyanide-containing wastewater is discharged into a water body, acute poisoning and even death of aquatic animals can be caused immediately. At present, the detection method of cyanide in the environment mainly adopts a volumetric method and a spectrophotometry method specified by national standards, and the methods are interfered by anions such as hypochlorite, sulfite ions, sulfide ions and the like to different degrees.
Rhodamine is a dye with excellent optical properties, and compared with other common fluorescent dyes, the rhodamine fluorescent dye has the advantages of good photostability, long-wavelength absorption, large absorption coefficient, high photostability in an open-loop form, insensitivity to pH, wider wavelength range, higher fluorescence quantum yield, long fluorescence lifetime and the like. Therefore, the fluorescent dye is widely applied to the aspects of pharmacology, physiology, molecular biology, cell biology, molecular genetics, environmental chemistry, single molecule detection, information science, fluorescent labeling, laser dye and the like, and is the most commonly used fluorescent dye in the fields of analytical chemistry and biomedical science in the biotechnology field. In recent years, rhodamine is widely used for the design and synthesis of metal ions and small molecule fluorescent probes, and the reason is that 2-carboxyl rhodamine and primary amine are amidated to generate stable leuco spiroimide, and then color and fluorescence are recovered after encountering metal ions or small molecules, so that the color change and the fluorescence detection of the metal ions and the organic small molecules are realized.
Disclosure of Invention
The invention aims to provide a spectrophotometry method for quantitatively detecting cyanide ions based on 2-aldehyde rhodamine derivatives without being interfered by anions.
The technical scheme adopted by the invention is as follows: the method for quantitatively detecting cyanide ions by a spectrophotometry based on the 2-aldehyde rhodamine derivatives comprises the following steps: adding a solution to be detected containing cyanide ions into a buffer solution of the 2-aldehyde rhodamine derivative, uniformly mixing, and measuring the absorbance at the maximum absorption peak under a spectrophotometer. The buffer solution of the 2-aldehyde rhodamine derivative is prepared by sequentially adding ethanol and disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution into the 2-aldehyde rhodamine derivative and uniformly mixing.
Further, in the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative, the pH of the buffer solution of the 2-aldehyde rhodamine derivative is 9.0.
Further, the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivativesIn the buffer solution of the 2-aldehyde rhodamine derivative, the concentration of the 2-aldehyde rhodamine derivative is (1-5) multiplied by 10-5mol/L。
Further, in the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative, the volume ratio of ethanol to disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution is 3: 7.
Further, in the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative, the 2-aldehyde rhodamine derivative has a structural general formula shown as (I):
wherein,
R1＝R2＝R3＝R4＝H；
or R1＝R4＝H，R2＝-CH2CH3，R3＝-CH3；
Or R1＝R2＝-CH3，R3＝R4＝H；
Or R1＝R2＝-CH2CH3，R3＝R4＝H；
Or R1And R4Together form- (CH)2)3-，R2And R3Together form- (CH)2)3-。
Further, in the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative, the preparation method of the 2-aldehyde rhodamine derivative comprises the following steps: taking rhodamine compounds, ethanolamine and absolute ethyl alcohol, reacting for 8-12h at 75-85 ℃, cooling to room temperature, filtering, dissolving the obtained solid in tetrahydrofuran solution, adding a reducing agent, stirring for 1-8 h at room temperature, adding water for quenching, extracting by dichloromethane, and purifying by column chromatography to obtain the 2-aldehyde rhodamine derivatives.
Further, in the method for quantitatively detecting cyanide ions by using the spectrophotometry based on the 2-aldehyde rhodamine derivative, the rhodamine compound is rhodamine B, rhodamine 6G, tetramethyl rhodamine TMR, rhodamine 110 or rhodamine 101.
Further, in the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative, the reducing agent is lithium aluminum hydride, lithium tri-tert-butoxyaluminum hydride, lithium triethoxyaluminum hydride, lithium diethoxyaluminum hydride or borane.
Furthermore, the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative comprises the following steps of (3-6) according to molar ratio, wherein the rhodamine compound is ethanolamine.
Furthermore, the method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivative comprises the following steps of (1-10) based on the molar ratio of the rhodamine compound and the reducing agent.
The invention has the beneficial effects that: the 2-aldehyde rhodamine compound is different from commercial 2-carboxyl rhodamine, and the mechanism for detecting cyanide is also different from that of 2-carboxyl rhodamine spiroimide. The 2-aldehyde rhodamine derivative has active aldehyde group and can perform nucleophilic reaction with cyanide ions, the generated oxyanion can further form a leuco body with a closed ring structure with rhodamine xanthene ring, and quantitative detection can be performed on the cyanide by respectively utilizing the change of absorbance in the reaction process.
Drawings
FIG. 1 is the color response of 2-aldehyde rhodamine derivative prepared in example 1 to cyanide in ultraviolet-visible absorption spectrum detection;
wherein, a is RhB-CHO; rh 6G-CHO; c is TMR-CHO; d is Rh 110-CHO; e, Rh 101-CHO.
FIG. 2 is the absorbance spectral response of RhB-CHO prepared in example 1 to cyanide.
FIG. 3 is a standard curve of RhB-CHO vs. cyanide ions prepared in example 1.
FIG. 4 is a standard plot of Rh6G-CHO versus cyanide ion prepared in example 1.
FIG. 5 is a standard curve of TMR-CHO prepared in example 1 against cyanide ions.
FIG. 6 is a standard curve of Rh110-CHO versus cyanide ion prepared in example 1.
FIG. 7 is a standard plot of Rh101-CHO versus cyanide ion prepared in example 1.
Detailed Description
The method for quantitatively detecting cyanide ions by a spectrophotometry based on the 2-aldehyde rhodamine derivatives comprises the following steps:
1. preparing a buffer solution of the 2-aldehyde rhodamine derivative: adding ethanol and disodium hydrogen phosphate-sodium dihydrogen phosphate (ethanol: disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution: 3:7 by volume ratio) into 2-aldehyde rhodamine derivative in sequence, and mixing to obtain 2-aldehyde rhodamine derivative with concentration of (1-5) × 10-5And (3) 2-aldehyde rhodamine derivative buffer solution with mol/L and pH of 9.0.
2. Drawing a standard curve: at a concentration of (1-5). times.10-5Adding known cyanide ion solutions with different concentrations into a buffer solution of the 2-aldehyde rhodamine derivative with the mol/L and the pH value of 9.0, respectively measuring the absorbance of the 2-aldehyde rhodamine derivative at the maximum absorption peak, and drawing the maximum absorption peak of the 2-aldehyde rhodamine derivative by taking the cyanide ion concentration as the abscissaThe absorbance at the peak is the standard curve of the ordinate.
3. And (3) determination: adding solution to be tested containing cyanide ions into the solution with the concentration of (1-5) multiplied by 10-5And (2) uniformly mixing the materials in a buffer solution of the 2-aldehyde rhodamine derivative with the mol/L and the pH value of 9.0, measuring the absorbance at the maximum absorption peak under a spectrophotometer, and finally calculating the concentration of cyanide ions in the solution to be detected through a standard curve.
The 2-aldehyde rhodamine derivative has a structural general formula shown as (I):
wherein,
R1＝R2＝R3＝R4＝H；
or R1＝R4＝H，R2＝-CH2CH3，R3＝-CH3；
Or R1＝R2＝-CH3，R3＝R4＝H；
Or R1＝R2＝-CH2CH3，R3＝R4＝H；
Or R1And R4Together form- (CH)2)3-，R2And R3Together form- (CH)2)3-。
The reaction general formula of the 2-aldehyde rhodamine derivative is as follows:
the preparation method of the 2-aldehyde rhodamine derivative comprises the following steps: weighing 1mol of rhodamine compound into a round-bottom flask, adding anhydrous ethanol and 3-6 times of ethanolamine by mol weight, heating at 75-85 ℃ for reaction for 8-12h, and cooling to room temperature to obtain light pink solid; dissolving the light pink solid in tetrahydrofuran solution, adding a reducing agent with the molar weight of 1-10 times, stirring at room temperature for 1-8 hours, adding water for quenching, extracting by dichloromethane, and purifying by column chromatography to obtain the 2-aldehyde rhodamine derivative.
The reducing agent is lithium aluminum hydride, lithium tri-tert-butoxyaluminum hydride, lithium triethoxyaluminum hydride, lithium diethoxyaluminum hydride or borane.
The rhodamine compound is rhodamine B, rhodamine 6G, tetramethyl rhodamine TMR, rhodamine 110 or rhodamine 101.
Example 12 qualitative and quantitative detection of Cyanid ions by Formylrhodamine derivatives
Preparation of (I) 2-aldehyde rhodamine derivatives
1. Preparation method of 2-aldehyde rhodamine B (RhB-CHO)
Adding 1mol of rhodamine B and 3mol of ethanolamine into dry 20mL of absolute ethanol in a round-bottom flask, carrying out oil bath reaction at 80 ℃ for 8-12h, cooling to room temperature, filtering, and washing the solid with ethanol for several times to obtain light pink solid; and dissolving the light pink solid in a tetrahydrofuran solution, adding 10mol of lithium aluminum hydride, stirring at room temperature for 1-8 hours, quenching the reaction liquid with water, extracting with dichloromethane, taking an organic phase, adding anhydrous magnesium sulfate, drying, and purifying by column chromatography to obtain a target product RhB-CHO. HRMS: 427.2386.
2. preparation method of 2-aldehyde rhodamine 6G (Rh6G-CHO)
Adding 1mol of rhodamine 6G and 4mol of ethanolamine into dry 20mL of absolute ethyl alcohol in a round-bottom flask, carrying out oil bath reaction at 80 ℃ for 8-12h, cooling to room temperature, filtering, and washing the solid with ethanol for several times to obtain pink solid; and dissolving the pink solid in a tetrahydrofuran solution, adding 10mol of lithium tri-tert-butoxyaluminum hydride, stirring at room temperature for 1-8 hours, quenching the reaction liquid with water, extracting with dichloromethane, taking an organic phase, adding anhydrous magnesium sulfate, drying, and purifying by column chromatography to obtain a target product Rh 6G-CHO. HRMS: 398.1994.
3. preparation method of 2-aldehyde tetramethyl rhodamine TMR (TMR-CHO)
Adding 1mol of tetramethyl rhodamine TMR and 5mol of ethanolamine into dry 20mL of absolute ethyl alcohol in a round-bottom flask, carrying out oil bath reaction at 80 ℃ for 8-12h, cooling to room temperature, filtering, and washing the solid with ethanol for several times to obtain pink solid; and dissolving the pink solid in a tetrahydrofuran solution, adding 8mol of lithium triethoxy aluminum hydride, stirring at room temperature for 1-8 hours, quenching the reaction liquid with water, extracting with dichloromethane, taking an organic phase, adding anhydrous magnesium sulfate, drying, and purifying by column chromatography to obtain a target product TMR-CHO. HRMS: 371.1760.
4. preparation method of 2-aldehyde rhodamine 110 (Rh110-CHO)
Adding 1mol of rhodamine 110 and 6mol of ethanolamine into dry 20mL of absolute ethanol in a round-bottom flask, carrying out oil bath reaction at 80 ℃ for 8-12h, cooling to room temperature, filtering, and washing the solid with ethanol for several times to obtain pink solid; and dissolving the pink solid in a tetrahydrofuran solution, adding 5mol of diethoxy lithium aluminum hydride, stirring at room temperature for 1-8 hours, quenching the reaction liquid with water, extracting with dichloromethane, taking an organic phase, adding anhydrous magnesium sulfate, drying, and purifying by column chromatography to obtain a target product Rh 110-CHO. HRMS: 315.1134.
5. preparation method of 2-aldehyde rhodamine 101 (Rh101-CHO)
Adding 1mol of rhodamine 101 and 5mol of ethanolamine into dry 20mL of absolute ethanol in a round-bottom flask, carrying out oil bath reaction at 80 ℃ for 8-12h, cooling to room temperature, filtering, and washing the solid with ethanol for several times to obtain pink solid; and dissolving the pink solid in a tetrahydrofuran solution, adding 6mol of lithium aluminum hydride, stirring at room temperature for 1-8 hours, quenching the reaction liquid with water, extracting with dichloromethane, taking an organic phase, adding anhydrous magnesium sulfate, drying, and purifying by column chromatography to obtain a target product Rh 101-CHO. HRMS: 475.2386.
qualitative detection of cyanide ions by (di) 2-aldehyde rhodamine derivatives
1. Preparing a buffer solution of the 2-aldehyde rhodamine derivative: adding ethanol and disodium hydrogen phosphate-sodium dihydrogen phosphate (ethanol: disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution: 3:7 by volume ratio) into 2-aldehyde rhodamine derivative in sequence, and mixing to obtain 2-aldehyde rhodamine derivative with concentration of 2 × 10-5And (3) 2-aldehyde rhodamine derivative buffer solution with mol/L and pH of 9.0.
2. And (3) determination: adding 2-aldehyde rhodamine derivative buffer solution obtained in the step 1) into the buffer solution respectively, wherein the concentration of the buffer solution is 2 multiplied by 10-4mol/L of different anions F-，Cl-，Br-，I-，CO3 2-，NO2-，H2PO4 -，HPO4 2-，SO4 2-，S2-，ClO-，CN-Etc. found except CN-Other anions than ions have no effect. As shown in FIG. 1, RhB-CHO (a), Rh6G-CHO (b), TMR-CHO (c), Rh110-CHO (d) and Rh101-CHO (e), the color of the solution is changed from pink to colorless within 1 minute only when the 2-aldehyde rhodamine derivative meets cyanide ions, the color is changed rapidly and visually, and the color can be seen by naked eyes, which shows that the 2-aldehyde rhodamine derivative can be used for CN-Has excellent selectivity, and can qualitatively distinguish and detect cyanide ions in a plurality of anions.
(III) quantitative detection of cyanide ions by RhB-CHO
1. Preparing a buffer solution of RhB-CHO: adding ethanol and disodium hydrogen phosphate-sodium dihydrogen phosphate (ethanol: disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution: 3:7 by volume ratio) into RhB-CHO in sequence, and mixing to obtain RhB-CHO with concentration of 2 × 10-5RhB-CHO buffer solution at mol/L, pH 9.0.
2. Drawing a standard curve: dissolving sodium cyanide in deionized water at a concentration of 0.008M to obtain a mother liquor.
At a concentration of 2X 10-5Adding known solutions containing cyanide ions and CN at different concentrations into RhB-CHO buffer solution at mol/L and pH 9.0-The concentration ratio of the CN to the RhB-CHO is 0 to 3.6, and CN is added at intervals of 0.1 time-The spectral change was measured and as shown in FIG. 2(RhB-CHO), the absorbance at 575nm of RhB-CHO was decreased with the addition of cyanide ion. Drawing a standard curve as shown in FIG. 3 with the absorbance of the maximum absorption peak at 575nm as the ordinate and the concentration of cyanide ion as the abscissa, wherein the linear range of cyanide ion corresponding to RhB-CHO standard curve is (0-1.8) × 10-5mol/L。
3. And (3) determination: adding solution to be tested containing cyanide ions into the solution with the concentration of 2 multiplied by 10-5mixing well in RhB-CHO buffer solution of mol/L and pH 9.0, measuring absorbance at 575nm in spectrophotometer after 2 min, and calculating by standard curve shown in FIG. 3The concentration of cyanide ions in the solution to be tested.
Quantitative detection of cyanide ions by (tetra) 2-aldehyde rhodamine derivatives
The method is the same as the method (III) and is different only in changing the 2-aldehyde rhodamine derivative.
FIGS. 4 to 7 show Rh6G-CHO, TMR-CHO, Rh110-CHO, Rh101-CHO concentrations of 2X 10-5And (3) a cyanide ion standard curve corresponding to mol/L and pH of 9.0.
As can be seen from FIGS. 4-7, the linear range of cyanide ions corresponding to Rh6G-CHO standard curve is (0-1). times.10-5mol/L. The linear range of cyanide ion corresponding to TMR-CHO standard curve is (0.3-1) × 10-5mol/L. The linear range of cyanide ion corresponding to Rh110-CHO standard curve is (0.5-1.2) x 10-5mol/L. The linear range of cyanide ion corresponding to Rh101-CHO standard curve is (0.2-1.2) x 10-5mol/L。
Claims (10)
1. The method for quantitatively detecting cyanide ions by spectrophotometry based on the 2-aldehyde rhodamine derivatives is characterized by comprising the following steps: adding a solution to be detected containing cyanide ions into a buffer solution of the 2-aldehyde rhodamine derivative, uniformly mixing, and measuring the absorbance at the maximum absorption peak under a spectrophotometer; the buffer solution of the 2-aldehyde rhodamine derivative is prepared by sequentially adding ethanol and disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution into the 2-aldehyde rhodamine derivative and uniformly mixing.
2. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 1, wherein the pH of the buffer solution of 2-aldehyde rhodamine derivatives is 9.0.
3. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 1, wherein the concentration of 2-aldehyde rhodamine derivatives in the buffer solution of 2-aldehyde rhodamine derivatives is (1-5) × 10-5mol/L。
4. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 1, wherein the ratio of ethanol to disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution is 3:7 by volume.
5. The method for quantitatively detecting cyanide ions based on the spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in any one of claims 1 to 4, wherein the 2-aldehyde rhodamine derivatives have the structural general formula shown as (I):
wherein,
R1＝R2＝R3＝R4＝H；
or R1＝R4＝H，R2＝-CH2CH3，R3＝-CH3；
Or R1＝R2＝-CH3，R3＝R4＝H；
Or R1＝R2＝-CH2CH3，R3＝R4＝H；
Or R1And R4Together form- (CH)2)3-，R2And R3Together form- (CH)2)3-。
6. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 5, wherein the preparation method of the 2-aldehyde rhodamine derivatives comprises the following steps: taking rhodamine compounds, ethanolamine and absolute ethyl alcohol, reacting for 8-12h at 75-85 ℃, cooling to room temperature, filtering, dissolving the obtained solid in tetrahydrofuran solution, adding a reducing agent, stirring for 1-8 h at room temperature, adding water for quenching, extracting by dichloromethane, and purifying by column chromatography to obtain the 2-aldehyde rhodamine derivatives.
7. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 6, wherein the rhodamine compound is rhodamine B, rhodamine 6G, tetramethyl rhodamine TMR, rhodamine 110 or rhodamine 101.
8. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 6, wherein the reducing agent is lithium aluminum hydride, lithium tri-tert-butoxyaluminum hydride, lithium triethoxyaluminum hydride, lithium diethoxyaluminum hydride or borane.
9. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 6, wherein the molar ratio of the rhodamine compound ethanolamine is 1 (3-6).
10. The method for quantitatively detecting cyanide ions based on spectrophotometry of 2-aldehyde rhodamine derivatives as claimed in claim 6, wherein the molar ratio of rhodamine compound to reducing agent is 1 (1-10).
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