CN105112049A - Sulfite ratiometric fluorescence probe and preparation method thereof - Google Patents
Sulfite ratiometric fluorescence probe and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical analysis detection, and particularly relates to a sulfite ratiometric fluorescence probe and a preparation method thereof. The molecular structural formula of the sulfite ratiometric fluorescence probe refers to description. The preparation method of the sulfite ratiometric fluorescence probe includes the following steps: reacting N1,N1 dimethyl benzene-1,4-diamine with crotonaldehyde to obtain N,N,2-trimethylquinoline-6-amine; reacting N,N,2-trimethylquinoline-6-amine with selenium dioxide to obtain 6-(dimethylamino) quinoline-2-formaldehyde; reacting 2,3,3-trimethylindoline with iodomethane to obtain 1,2,3,3-tetramethyl-3H-indoliu iodide; reacting 6-(dimethylamino) quinoline-2-formaldehyde and 1,2,3,3-tetramethyl-3H-indoliu iodide with piperidine to obtain the probe. According to the invention, molecular synthesis of the probe is simple, the cost is relatively low, the selectivity to sulfite is good, the preparation method is simple, raw materials are cheap and easy to obtain, and the method is easy to realize.
Description
Technical field
The invention belongs to chemical analysis detection technique field, be specifically related to a kind of inferior sulfate radical ratio fluorescent probe and preparation method thereof.
Background technology
Sulphite is a kind of important foodstuff additive, and people takes in a small amount of sulphite and can not damage health, but takes in that too much sulphite may cause gastrointestinal disorders, causes tormina, renal tubal dysfunction disease.Especially to the people of sulphite allergy, even if take in a small amount of sulphite also easily cause asthma, allergic, gastrointestinal upset etc.In addition, containing too much sulphite in trade effluent, the concentration of oxygen in water can be had a strong impact on, thus ecotope is worked the mischief.Therefore, inventing convenient and swift, that High sensitivity detects sulfite content method is very important to food safety and environment measuring.
Summary of the invention
The object of this invention is to provide a kind of inferior sulfate radical ratio fluorescent probe, molecule synthesis is simple, good to the selectivity of inferior sulfate radical; Invention also provides the preparation method of inferior sulfate radical ratio fluorescent probe, cheaper starting materials is easy to get, synthesis technique is simple, be easy to realize.
Inferior sulfate radical ratio fluorescent probe of the present invention, molecular structural formula is as follows:
Chinese is by name: 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
The preparation method of inferior sulfate radical ratio fluorescent probe of the present invention, step is as follows:
(1) N1, N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines is dissolved in hydrochloric acid soln, then adds crotonic aldehyde, and acetone reacts until react completely as solvent refluxing, concentrating under reduced pressure, and in crude product and after extraction, column chromatography obtains product N, N, 2-trimethylquinoline-6-amine;
(2) by compound N, N, 2-trimethylquinoline-6-amine and tin anhydride are dissolved in Rong Ji diox/water, and return stirring is until react completely, and crude product to be purified to obtain product 6-(dimethylamino) quinoline-2-formaldehyde by column chromatography;
(3) compound 2,3,3-trimethylammonium indoline, methyl iodide are dissolved in toluene, return stirring, TLC detects until react completely, and concentrating under reduced pressure obtains crude product, and crude product hexane ultrasonication obtains solid tan product 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide;
(4) by product 6-(dimethylamino) quinoline-2-formaldehyde, 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide, piperidines are dissolved in dehydrated alcohol, return stirring, TLC detects until react completely, filter to obtain crude product, crude product organic solvent rinses, dry final product 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
The mol ratio of the N1 described in step (1), N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines and crotonic aldehyde is 1:2-3, and the volume ratio of hydrochloric acid soln and acetone is 1-3:1.
The ratio of the N1 described in step (1), N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines and acetone is 1:1-2, and wherein, N1, N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines is with molar basis, and acetone is in volume liter.
N described in step (2), the mol ratio of N, 2-trimethylquinoline-6-amine and tin anhydride is 1:1-2; The ratio of N, N, 2-trimethylquinoline-6-amine, diox and water is 1:100-200:10-20, wherein, N, N, 2-trimethylquinoline-6-amine in molar basis ， diox and water with volume liter.
The mol ratio of compound 2,3, the 3-trimethylammonium indoline described in step (3) and methyl iodide is 1:1-2.
The ratio of compound 2,3, the 3-trimethylammonium indoline described in step (3) and toluene is 1:3-5; Wherein, compound 2,3,3-trimethylammonium indoline is with molar basis, and toluene is in volume liter.
The mol ratio of 6-(dimethylamino) quinoline-2-formaldehyde, 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide and the piperidines described in step (4) is 1:1-2:0.5-2.
The ratio of 6-(dimethylamino) quinoline-2-formaldehyde described in step (4) and ethanol is 1:3-6, and wherein 6-(dimethylamino) quinoline-2-formaldehyde is with molar basis, and ethanol is in volume liter.
Organic solvent described in step (4) is the one in methyl alcohol, ethanol, ether, acetone, acetonitrile or normal hexane.
Synthetic route is as follows:
The present invention compared with prior art, has following beneficial effect:
Probe molecule synthesis of the present invention is simple, and cost is lower, good to the selectivity of inferior sulfate radical, has actual using value in the field such as biological chemistry, environmental science.Preparation method is simple, and cheaper starting materials is easy to get, and is easy to realize.
Embodiment
Below in conjunction with embodiment, the present invention is described further.
Embodiment 1
(1) compound N 1, N1 dimethyl benzene-1,4-diamines (5g, 36.7mmol) be dissolved in hydrochloric acid soln (6M, 66mL), then add crotonic aldehyde (6.0mL, 73.5mmol), after stirred at ambient temperature 1h, add acetone (35mL) solvent refluxing and stir 12h.Be cooled to room temperature after reacting completely, removing organic phase, it is 7 that liquid phase sodium hydroxide solution neutralizes PH, and then add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product N is obtained through column chromatography (methylene dichloride: methyl alcohol=1:1) separating-purifying, N, 2-trimethylquinoline-6-amine.
(2) compound N, N, 2-trimethylquinoline-6-amine (1mmol), tin anhydride (1mmol) are dissolved in diox/water (140mL/14mL) mixing solutions, return stirring 4h.After TLC detection reaction is complete, be cooled to room temperature, add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product 6-(dimethylamino) quinoline-2-formaldehyde is obtained through column chromatography (methylene dichloride: methyl alcohol=98:2) separating-purifying.
(3) 2,3,3-trimethylammonium indoline (3.0g, 18.8mmol) and methyl iodide (3.2g, 22.6mmol) are dissolved in 60mL toluene, at 80 DEG C, stir 48h.By reaction solution cool to room temperature, concentrating under reduced pressure obtains crude product.Crude product is suspended in 100mL hexane, and ultrasonication 10min also filters, and obtains solid tan product 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide.
(4) by product 6-(dimethylamino) quinoline-2-formaldehyde (100mg, 0.5mmol), 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide (166mg, 0.55mmol) and piperidines (5 μ L) are dissolved in 15mL dehydrated alcohol, return stirring 8h.After reacting completely, solution is cooled to room temperature, filters to obtain solid crude product.Crude product 20mL Rinsed with cold methanol, dry final product 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
Embodiment 2
(1) compound N 1, N1 dimethyl benzene-1,4-diamines (5g, 36.7mmol) be dissolved in hydrochloric acid soln (6M, 60mL), then add crotonic aldehyde (7.5mL, 91.75mmol), after stirred at ambient temperature 2h, add acetone (50mL) solvent refluxing and stir 10h.Be cooled to room temperature after TLC monitoring reacts completely, removing organic phase, it is 7 that liquid phase sodium hydroxide solution neutralizes PH, then add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product N is obtained through column chromatography (methylene dichloride: methyl alcohol=1:1) separating-purifying, N, 2-trimethylquinoline-6-amine.
(2) compound N, N, 2-trimethylquinoline-6-amine (1mmol), tin anhydride (1.5mmol) are dissolved in diox/water (100mL/12mL) mixing solutions, return stirring 5h.After TLC detection reaction is complete, be cooled to room temperature, add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product 6-(dimethylamino) quinoline-2-formaldehyde is obtained through column chromatography (methylene dichloride: methyl alcohol=98:2) separating-purifying.
(3) 2,3,3-trimethylammonium indoline (3.0g, 18.8mmol) and methyl iodide (2.7g, 18.8mmol) are dissolved in 80mL toluene, return stirring 35h.By reaction solution cool to room temperature, concentrating under reduced pressure obtains crude product.Crude product is suspended in 120mL hexane, and ultrasonication 15min also filters, and obtains solid tan product 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide.
(4) by product 6-(dimethylamino) quinoline-2-formaldehyde (100mg, 0.5mmol), 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide (226mg, 0.75mmol) and piperidines (7.2 μ L) be dissolved in 30mL dehydrated alcohol, return stirring 5h.After reacting completely, solution is cooled to room temperature, filters to obtain solid crude product.Crude product 20mL cold acetone rinses, dry final product 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
Embodiment 3
(1) compound N 1, N1 dimethyl benzene-1,4-diamines (5g, 36.7mmol) be dissolved in hydrochloric acid soln (6M, 75mL), then add crotonic aldehyde (8.99mL, 110mmol), after stirred at ambient temperature 1.5h, add acetone (40mL) solvent refluxing and stir 10h.Be cooled to room temperature after TLC monitoring reacts completely, removing organic phase, it is 7 that liquid phase sodium hydroxide solution neutralizes PH, then add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product N is obtained through column chromatography (methylene dichloride: methyl alcohol=1:1) separating-purifying, N, 2-trimethylquinoline-6-amine.
(2) compound N, N, 2-trimethylquinoline-6-amine (1mmol), tin anhydride (2mmol) are dissolved in diox/water (200mL/20mL) mixing solutions, return stirring 4h.After TLC detection reaction is complete, be cooled to room temperature, add methylene dichloride (50mL × 3) extraction 3 times, collect organic phase, anhydrous sodium sulfate drying, underpressure distillation, except desolventizing, obtains crude product.Then product 6-(dimethylamino) quinoline-2-formaldehyde is obtained through column chromatography (methylene dichloride: methyl alcohol=98:2) separating-purifying.
(3) 2,3,3-trimethylammonium indoline (3.0g, 18.8mmol) and methyl iodide (5.3g, 37.6mmol) are dissolved in 120mL toluene, return stirring 40h.By reaction solution cool to room temperature, concentrating under reduced pressure obtains crude product.Crude product is suspended in 120mL hexane, and ultrasonication 15min also filters, and obtains solid tan product 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide.
(4) by product 6-(dimethylamino) quinoline-2-formaldehyde (100mg, 0.5mmol), 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide (302mg, 1.0mmol) and piperidines (10 μ L) be dissolved in 40mL dehydrated alcohol, return stirring 10h.After reacting completely, solution is cooled to room temperature, filters to obtain solid crude product.Crude product 30mL cold diethyl ether rinses, dry final product 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
Claims (10)
1. an inferior sulfate radical ratio fluorescent probe, is characterized in that molecular structural formula is as follows:
2. a preparation method for inferior sulfate radical ratio fluorescent probe according to claim 1, is characterized in that step is as follows:
(1) N1, N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines is dissolved in hydrochloric acid soln, then adds crotonic aldehyde, and acetone reacts until react completely as solvent refluxing, concentrating under reduced pressure, and in crude product and after extraction, column chromatography obtains product N, N, 2-trimethylquinoline-6-amine;
(2) by compound N, N, 2-trimethylquinoline-6-amine and tin anhydride are dissolved in Rong Ji diox/water, and return stirring is until react completely, and crude product to be purified to obtain product 6-(dimethylamino) quinoline-2-formaldehyde by column chromatography;
(3) compound 2,3,3-trimethylammonium indoline, methyl iodide are dissolved in toluene, return stirring, TLC detects until react completely, and concentrating under reduced pressure obtains crude product, and crude product hexane ultrasonication obtains solid tan product 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide;
(4) by product 6-(dimethylamino) quinoline-2-formaldehyde, 1,2,3,3-tetramethyl--3 hydrogen-indoles iodide, piperidines are dissolved in dehydrated alcohol, return stirring, TLC detects until react completely, filter to obtain crude product, crude product organic solvent rinses, dry final product 2-(2-(6-(dimethylamino) quinoline-2-base) vinyl)-1,3,3-trimethylammonium-3H-indoles-1-iodide.
3. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, it is characterized in that the N1 described in step (1), the mol ratio of N1 dimethyl benzene-Isosorbide-5-Nitrae-diamines and crotonic aldehyde is 1:2-3, and the volume ratio of hydrochloric acid soln and acetone is 1-3:1.
4. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, it is characterized in that the N1 described in step (1), N1 dimethyl benzene-1, the ratio of 4-diamines and acetone is 1:1-2, wherein, N1, N1 dimethyl benzene-1,4-diamines is with molar basis, and acetone is in volume liter.
5. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, is characterized in that the N described in step (2), and the mol ratio of N, 2-trimethylquinoline-6-amine and tin anhydride is 1:1-2; The ratio of N, N, 2-trimethylquinoline-6-amine, diox and water is 1:100-200:10-20, wherein, N, N, 2-trimethylquinoline-6-amine in molar basis ， diox and water with volume liter.
6. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, is characterized in that the mol ratio of compound 2,3, the 3-trimethylammonium indoline described in step (3) and methyl iodide is 1:1-2.
7. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, is characterized in that the ratio of compound 2,3, the 3-trimethylammonium indoline described in step (3) and toluene is 1:3-5; Wherein, compound 2,3,3-trimethylammonium indoline is with molar basis, and toluene is in volume liter.
8. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, it is characterized in that 6-(dimethylamino) quinoline-2-formaldehyde, 1 described in step (4), 2, the mol ratio of 3,3-tetramethyl--3 hydrogen-indoles iodide and piperidines is 1:1-2:0.5-2.
9. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, the ratio that it is characterized in that 6-(dimethylamino) quinoline-2-formaldehyde described in step (4) and ethanol is 1:3-6, wherein 6-(dimethylamino) quinoline-2-formaldehyde is with molar basis, and ethanol is in volume liter.
10. the preparation method of inferior sulfate radical ratio fluorescent probe according to claim 2, is characterized in that the organic solvent described in step (4) is the one in methyl alcohol, ethanol, ether, acetone, acetonitrile or normal hexane.
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Cited By (9)
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| CN106674183A (en) * | 2016-12-29 | 2017-05-17 | 济南大学 | Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof |
| CN108102647A (en) * | 2018-03-06 | 2018-06-01 | 泰山医学院 | Imidazopyridine cyanofuran class inferior sulfate radical fluorescence probe and its application |
| CN108226106A (en) * | 2017-11-07 | 2018-06-29 | 泰山医学院 | Ratio-type sulfite ion fluorescence probe based on half flower cyanines of indolizine-cyanofuran |
| CN108383835A (en) * | 2017-10-12 | 2018-08-10 | 泰山医学院 | Pyrido [1,2-a] the benzimidazole hypochlorous acid fluorescence probe of indoles modification and its application |
| CN108623575A (en) * | 2017-03-21 | 2018-10-09 | 泰山医学院 | A kind of fluorescence probe that is simple and effectively detecting sulphite |
| CN108676554A (en) * | 2018-05-10 | 2018-10-19 | 郑州大学 | A kind of composite Nano probe and preparation method thereof and application |
| CN110343403A (en) * | 2019-07-23 | 2019-10-18 | 哈尔滨工业大学（威海） | A kind of pyrazolines dyestuff and preparation method thereof identifying inferior sulfate radical |
| CN110386931A (en) * | 2018-04-20 | 2019-10-29 | 南京大学 | A kind of human albumin's fluorescence probe and its preparation method and purposes |
| CN111635394A (en) * | 2020-06-24 | 2020-09-08 | 哈尔滨工业大学（威海） | Pyrazoline sulfite fluorescent probe and preparation method thereof |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106674183B (en) * | 2016-12-29 | 2018-12-18 | 济南大学 | A kind of Ratio-type inferior sulfate radical fluorescence probe and preparation method thereof and biologic applications |
| CN106674183A (en) * | 2016-12-29 | 2017-05-17 | 济南大学 | Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof |
| CN108623575B (en) * | 2017-03-21 | 2020-04-10 | 山东第一医科大学(山东省医学科学院) | Simple and effective fluorescent probe for detecting sulfite |
| CN108623575A (en) * | 2017-03-21 | 2018-10-09 | 泰山医学院 | A kind of fluorescence probe that is simple and effectively detecting sulphite |
| CN108383835A (en) * | 2017-10-12 | 2018-08-10 | 泰山医学院 | Pyrido [1,2-a] the benzimidazole hypochlorous acid fluorescence probe of indoles modification and its application |
| CN108226106A (en) * | 2017-11-07 | 2018-06-29 | 泰山医学院 | Ratio-type sulfite ion fluorescence probe based on half flower cyanines of indolizine-cyanofuran |
| CN108102647A (en) * | 2018-03-06 | 2018-06-01 | 泰山医学院 | Imidazopyridine cyanofuran class inferior sulfate radical fluorescence probe and its application |
| CN110386931A (en) * | 2018-04-20 | 2019-10-29 | 南京大学 | A kind of human albumin's fluorescence probe and its preparation method and purposes |
| CN110386931B (en) * | 2018-04-20 | 2022-04-22 | 南京大学 | Human serum protein fluorescent probe and preparation method and application thereof |
| CN108676554A (en) * | 2018-05-10 | 2018-10-19 | 郑州大学 | A kind of composite Nano probe and preparation method thereof and application |
| CN108676554B (en) * | 2018-05-10 | 2020-12-01 | 郑州大学 | Composite nano probe and preparation method and application thereof |
| CN110343403A (en) * | 2019-07-23 | 2019-10-18 | 哈尔滨工业大学（威海） | A kind of pyrazolines dyestuff and preparation method thereof identifying inferior sulfate radical |
| CN111635394A (en) * | 2020-06-24 | 2020-09-08 | 哈尔滨工业大学（威海） | Pyrazoline sulfite fluorescent probe and preparation method thereof |
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Application publication date: 20151202 |