CN104987346A - Method for preparing fluorescence polyamino compound - Google Patents
Method for preparing fluorescence polyamino compound Download PDFInfo
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- CN104987346A CN104987346A CN201510216058.4A CN201510216058A CN104987346A CN 104987346 A CN104987346 A CN 104987346A CN 201510216058 A CN201510216058 A CN 201510216058A CN 104987346 A CN104987346 A CN 104987346A
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Abstract
The invention relates to a method for preparing a fluorescence polyamino compound through processing polyacid by thionyl chloride and reacting the above obtained material with an amino compound. The method comprises the following steps: dissolving the polyacid by using tetrahydrofuran, adding a tetrahydrofuran solution of thionyl chloride in a dropwise manner, reacting, and removing thionyl chloride to obtain a mixture I; adding the amino compound to the mixture I to obtain a mixture II, washing the mixture II by using petroleum ether 3 times, separating out the obtained tetrahydrofuran layer by using a separating funnel, and carrying out reduced pressure evaporation to remove tetrahydrofuran in order to obtain a crude product III; and dissolving a polyamido compound in the crude product III by using chloroform, centrifuging or filtering, and carrying out reduced pressure evaporation to remove chloroform in order to obtain the fluorescence polyamido compound. The compound obtained through the method is fluorescent due to the polyamido group in the molecular structure, and the fluorescence quantum intensity and the fluorescence color of the finished product are different by changing different amino compounds. Organic solvents used in the preparation process can be recycled.
Description
Technical field
The present invention relates to a kind of preparation method with the multiamide based compound of fluorescence, particularly relate to and adopt carboxylic acid to be reaction substrate, thionyl chloride, as acyl chlorides reagent, reacts with aminocompound the method generating the multiamide based compound with fluorescence.
Background technology
Organic molecule has fluorescent characteristic, be mostly due in molecule with conjugation heterocycle and various chromophore, change its conjugate length by introducing the unsaturated group such as ethylene linkage, phenyl ring and various chromophore, thus compound optoelectronic character changed.Wherein amido linkage is conventional connection conjugation heterocycle and functional group of chromophore, but yet there are no both at home and abroad and only generate multiamide key and have the compound of photoluminescent property.
Summary of the invention
In order to solve above technical problem, the invention provides a kind of preparation method with the multiamide based compound of fluorescence.This multiamide based compound can be used for ion concentration of mercury in test water.
Technical scheme of the present invention is as follows:
Have a preparation method for the multiamide based compound of fluorescence, step is as follows:
1) under the condition passing into nitrogen, dissolve carboxylic acid with tetrahydrofuran (THF), after dropwise instilling the thionyl chloride solution of tetrahydrofuran (THF) dilution, after stirring, add aminocompound (primary amine or secondary amine) reaction.Steam unnecessary thionyl chloride after having reacted, obtain the mixture I that main component is polynary acyl chlorides;
2) with tetrahydrofuran (THF) dissolving mixt I, after adding aminocompound stirring, the mixtures II that main component is polynary amide compound is obtained;
3) after mixtures II being washed three times with sherwood oil, isolate tetrahydrofuran (THF) layer with separating funnel, the decompression tetrahydrofuran (THF) steamed in mixture obtains crude product III;
4) dissolve crude product III with chloroform, after filtration, chloroform decompression in chloroformic solution is steamed, finally obtain the multiamide based compound with fluorescence.
Above-mentioned steps 1) in carboxylic acid select polyprotonic acid, preferred polyprotonic acid is citric acid, and the quantum yield of its product is general higher;
Above-mentioned steps 1) in, preferred polyprotonic acid and tetrahydrofuran (THF) mass ratio are about 1:25 ~ 1:30, under this ratio, reaction temperature and and the usage quantity of solvent is moderate;
Above-mentioned steps 1) in polyprotonic acid and thionyl chloride mol ratio be about (
1:n) ~ (1:1.05n);
Above-mentioned steps 1) in tetrahydrofuran (THF) and thionyl chloride volume ratio be about (
5:1) ~ (50:1); (also needing both quantity relative ratio relationship in the thionyl chloride solution of tetrahydrofuran (THF) dilution)
Above-mentioned steps 1) in preferred range of reaction temperature be 0 DEG C ~ 30 DEG C, the reaction times is 1 ~ 4hr;
Above-mentioned steps 2) in aminocompound, preferably aminoethylaminopropyl dimethoxysilane, allylamine.When reaction substrate is citric acid and N-(β-aminoethyl-γ-aminopropyl) methyl dimethoxysilane time, the quantum yield of its product is 10.7%, under 365nm ultra violet lamp, fluorescence color is pearl opal, when aminocompound is diethylamide, under 365nm ultra violet lamp, fluorescence color is yellow-green colour.
Above-mentioned steps 2) in polyprotonic acid and the mol ratio of aminocompound, preferably (
1:n) ~ (1:1.1n), wherein
nfor the number of-COOH in polyprotonic acid.
Above-mentioned steps 2) in, temperature of reaction preferable range is 30 ~ 50 DEG C, and this range of reaction temperature easily controls, and by product is few in this temperature range.Reaction times is preferably 30min ~ 1hr, and in this reaction times, reaction efficiency is high.
Above-mentioned steps 3) in, preferred mixtures II is about (75 ~ 150) with the ratio of sherwood oil cumulative volume: 750, and under this ratio, sherwood oil consumption is moderate, and aminocompound nonreactive in reaction system can be cleaned up.
Above-mentioned steps 4) in, preferred crude product III is 1:(25 ~ 35 with the ratio of the volume of chloroform), under this ratio, chloroform consumption is moderate, and can dissolve the fluorescence multiamide compound in crude product II completely.
Concrete chemical reaction is as follows:
。
The good results effect of the inventive method is as follows:
1. the preparation method's processing ease that the present invention relates to.Just can obtain having compared with high-fluorescence quantum yield by means of only lower temperature with in the short period, the multiamide based compound of multiple fluorescence color.
2. the multiamide based compound quantum yield that obtains of the present invention is higher.Adopt preparation method of the present invention, the quantum yield of multiamide based compound is up to 40.7%.
3. the preparation method's economical effectiveness that the present invention relates to is obvious, the recyclable recycling of the solvent in each preparation process.
Accompanying drawing explanation
Fig. 1 is the absorption spectrum with the multiamide based compound of fluorescence, excitation spectrum and emmission spectrum prepared by embodiment 1.
Fig. 2 is the emmission spectrum of multiamide based compound under different excitation wavelength with fluorescence prepared by embodiment 1.
Fig. 3 is the Characterization of The Products figure with the multiamide based compound of fluorescence prepared by embodiment 2.
Embodiment
Below in conjunction with example, the present invention will be further described, but be not limited thereto.
Raw materials used Citric Acid, usp, Anhydrous Powder in embodiment, the third three acid, oxysuccinic acid, diethylamide, quadrol, diethylamine, allylamine, N-(β-aminoethyl-γ-aminopropyl) methyl dimethoxysilane, thionyl chloride, tetrahydrofuran (THF), sherwood oil, chloroform (trichloromethane) is commercially available.
Embodiment 1
The preparation of fluorescence citric mide, step is as follows:
1. getting 2g citric acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 2.7ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:3.2) and be placed in constant pressure funnel, then with 2.3 ml tetrahydrofuran (THF) dilutions, then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h at 40 DEG C, steam unnecessary thionyl chloride, obtain transparent liquid I
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid I, add N-(β-aminoethyl-γ-aminopropyl) methyl dimethoxysilane 10 ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 2g;
4. with the product in 50mL chloroform extraction crude product III, centrifugation or after filtering again decompression steam chloroform, obtain the multiamide based compound CA-Si with fluorescence.
The multiamide based compound above gained with fluorescence has done fluorometric investigation.Fig. 1 is the absorption spectrum of the multiamide based compound with fluorescence, excitation spectrum and emmission spectrum.Insert pictures is the photo of fluorescent small molecule solution under natural light (left side) and UV-light (right side).Fig. 2 is its emmission spectrum under different excitation wavelength (excitation wavelength difference is 20nm).Be reference substance with Quinine Sulphate Di HC, the fluorescence quantum yield obtaining multiamide based compound is 40.7%.
Embodiment 2
The preparation of fluorescence citric mide, step is as follows:
1. getting 2g citric acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 1.45ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:2) and be placed in constant pressure funnel, then with 1.55 ml tetrahydrofuran (THF) dilutions, then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h in 0 DEG C of environment, add 20ml normal hexane decompress filter three times, steam remaining thionyl chloride, obtain transparent liquid I;
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid, add diethylamide 10 ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 1.25g.
4. with the product in 50mL tetrachloromethane extraction crude product III, centrifugation or after filtering again decompression steam tetrachloromethane, obtain the multiamide based compound CA with fluorescence;
Products therefrom phenogram as Fig. 3 fluorescent small molecule CA solution ultraviolet absorptivity, excite, launch collection of illustrative plates; And fluorescent small molecule is at the photo of natural light (right side) and UV-light (left side).Be reference substance with Quinine Sulphate Di HC, the fluorescence quantum yield obtaining multiamide based compound is 37.6%.
Embodiment 3
The preparation of the sour acid amides of fluorescence the third three, step is as follows:
1. getting 2g the third three acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 2.5ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:2) and be placed in constant pressure funnel, then with 1.5 ml tetrahydrofuran (THF) dilutions, then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h in 0 DEG C of environment, add 20ml normal hexane decompress filter three times, steam remaining thionyl chloride, obtain transparent liquid I;
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid, add diethylamide and N-(β-aminoethyl-γ-aminopropyl) methyl dimethoxysilane 10 ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 0.7g;
4. with the product in 50mL chloroform extraction crude product III, centrifugation or after filtering again decompression steam chloroform, obtain the multiamide based compound with fluorescence.
Products therefrom characterizes with example 1 similar, fluorescence quantum yield 10.5%.
Embodiment 4
The preparation of the sour acid amides of fluorescence the third three, step is as follows:
1. getting 2g the third three acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 1.4ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:2.2) and be placed in constant pressure funnel, then with the dilution of 2.6ml tetrahydrofuran (THF), then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h in 0 DEG C of environment, add 20ml normal hexane decompress filter three times, steam unnecessary thionyl chloride, obtain transparent liquid I;
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid, add appropriate N-(β-aminoethyl-γ-aminopropyl) methyl dimethoxysilane 10 ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 2.05g.
4. with the product in 50mL dichloromethane extraction crude product III, centrifugation or after filtering again decompression steam methylene dichloride, obtain the multiamide based compound with fluorescence.
Embodiment 5
The preparation of fluorescence citric mide, step is as follows:
1. getting 2g oxysuccinic acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 2.7ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:2.2) and be placed in constant pressure funnel, then with the dilution of 2.3ml tetrahydrofuran (THF), then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h in 0 DEG C of environment, add 20ml normal hexane decompress filter three times, steam unnecessary thionyl chloride, obtain transparent liquid I;
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid, add allylamine 10ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 1.45g.
4. with the product in 50mL dichloromethane extraction crude product III, centrifugation or after filtering again decompression steam methylene dichloride, obtain the multiamide based compound with fluorescence.
Embodiment 6
The preparation of fluorescence citric mide, step is as follows:
1. getting 2g citric acid adds in there-necked flask, add 30ml tetrahydrofuran (THF) to dissolve, slowly pass into nitrogen, get 1.45ml thionyl chloride (citric acid and thionyl chloride mol ratio are 1:2.2) and be placed in constant pressure funnel, then with the dilution of 1.55ml tetrahydrofuran (THF), then dropwise add in the citric acid of dissolving, by this device as after uniform stirring 12h in 0 DEG C of environment, add 20ml normal hexane decompress filter three times, steam unnecessary thionyl chloride, obtain transparent liquid I;
2. get 2ml tetrahydrofuran (THF) dilution transparent liquid, add allylamine 10 ml, vigorous stirring half an hour, obtain mixtures II;
3. mixtures II is cleaned three times with 35mL sherwood oil respectively, tetrahydrofuran (THF) layer isolated by separating funnel, and then decompression steams tetrahydrofuran (THF), obtains crude product III and is about 0.9g.
4. with the product in 50mL chloroform extraction crude product III, centrifugation or after filtering again decompression steam chloroform, obtain the multiamide based compound with fluorescence.
Claims (10)
1. there is a preparation method for the multiamide based compound of fluorescence, it is characterized in that, comprise the steps:
1) under the condition passing into nitrogen, dissolve carboxylic acid with tetrahydrofuran (THF), after dropwise instilling the thionyl chloride solution of tetrahydrofuran (THF) dilution, after stirring, add aminocompound reaction, steam unnecessary thionyl chloride after reacting completely, obtain the mixture I that main component is polynary acyl chlorides;
2) with tetrahydrofuran (THF) dissolving mixt I, after adding aminocompound stirring, the mixtures II that main component is polynary amide compound is obtained;
3) after mixtures II being washed three times with sherwood oil, isolate tetrahydrofuran (THF) layer with separating funnel, the decompression tetrahydrofuran (THF) steamed in mixture obtains crude product III;
4) dissolve crude product III with chloroform, after filtration, chloroform decompression in chloroformic solution is steamed, finally obtain the multiamide based compound with fluorescence.
2. preparation method according to claim 1, is characterized in that, the carboxylic acid in step 1) is polyprotonic acid.
3. preparation method according to claim 2, is characterized in that, described polyprotonic acid is citric acid.
4. preparation method according to claim 1, is characterized in that, in step 1), carboxylic acid and tetrahydrofuran (THF) mass ratio are 1:25 ~ 1:30; Carboxylic acid acid is 1:(1-1.05 with thionyl chloride mol ratio) n, wherein n is the number of-COOH in polyprotonic acid; Tetrahydrofuran (THF) and thionyl chloride volume ratio are (5-50): 1.
5. preparation method according to claim 1, is characterized in that, in step 1), range of reaction temperature is 0 DEG C ~ 30 DEG C, and the reaction times is 1 ~ 4hr.
6. preparation method according to claim 1, is characterized in that, step 2) in, described aminocompound is the one in aminoethylaminopropyl dimethoxysilane, allylamine.
7. preparation method according to claim 1, is characterized in that, step 2) in, the mol ratio of polyprotonic acid and aminocompound is 1:(1-1.1) n, wherein n is the number of-COOH in polyprotonic acid.
8. preparation method according to claim 1, is characterized in that, step 2) in, range of reaction temperature is 30 ~ 50 DEG C,
Reaction times is 30min ~ 1hr.
9. preparation method according to claim 1, is characterized in that, in step 3), mixtures II is (1 ~ 2) with the ratio of sherwood oil cumulative volume: 10.
10. preparation method according to claim 1, is characterized in that, in step 4), crude product III is 1:(25 ~ 35 with the ratio of the volume of chloroform).
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| CN107952403A (en) * | 2017-12-04 | 2018-04-24 | 济南大学 | A kind of fluorescent silicon dioxide method for preparing microsphere of Quantitative detection iron ion |
| CN114133570A (en) * | 2021-11-16 | 2022-03-04 | 北京科技大学 | Self-repairing polysiloxane elastomer and preparation method thereof |
| CN115684103A (en) * | 2022-09-15 | 2023-02-03 | 济南大学 | Method for quantitatively detecting pH value of cement by using ratio type fluorescent probe |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107952403A (en) * | 2017-12-04 | 2018-04-24 | 济南大学 | A kind of fluorescent silicon dioxide method for preparing microsphere of Quantitative detection iron ion |
| CN107892914A (en) * | 2017-12-08 | 2018-04-10 | 济南大学 | A kind of quick identification and the fluorescent microsphere preparation method for quantitatively detecting mercury ion |
| CN114133570A (en) * | 2021-11-16 | 2022-03-04 | 北京科技大学 | Self-repairing polysiloxane elastomer and preparation method thereof |
| CN115684103A (en) * | 2022-09-15 | 2023-02-03 | 济南大学 | Method for quantitatively detecting pH value of cement by using ratio type fluorescent probe |
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