CN102942541A - Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions - Google Patents
Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions Download PDFInfo
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Abstract
The invention discloses a receptor compound as well as synthesis and application of the receptor compound in colorimetric detection of fluorine ions, belonging to the field of organic chemical synthesis. By using a 5-(4-nitryl)phenyl-2-furfural group as a signal report group, the receptor has the colorimetric recognition capability; and by using an acylhydrazone group as a recognition site, the compound can be better combined with the fluorine ions, so that the receptor compound can be used for detecting and recognizing the fluorine ions. A test shows that in the DMSO solution, the receptor compound has colorimetric recognition capability on fluorine ions. The acceptor compound is dissolved in DMF (Dimethyl Formamide) to prepare a 1%-1.5% by mass solution and the solution is cooled to the room temperature to form organic gel; and the organic gel is capable of carrying out colorimetric detection on the fluorine ions in the DMSO (Dimethyl Sulfoxide) solution and has the advantages of good heat stability, high detection sensitivity and the like, and is convenient to carry and use.
Description
Technical field
The invention belongs to negatively charged ion detection technique field, relate to a kind of acceptor compound---thing 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone, the present invention relates to the synthetic method of this receptor compound simultaneously; The invention still further relates to the application of this receptor compound do in the colorimetric detection fluorion.
Technical field
Along with supramolecular chemistry is fast-developing, the research of Anion Recognition is also deepened continuously thereupon.Negatively charged ion embodies more and more important effect in the fields such as biology, medicine, catalysis, environment, the detection of negatively charged ion is also being become a very necessary job, and therefore, design synthetic anionic sensor more and more is subject to investigator's attention.In Anion Recognition, main selectivity changes (colorimetric detection method) its solution colour after in conjunction with the object negatively charged ion, does not need valuable instrument, simple operation and other advantages because this method has, so obtained very widely research.Fluorion is a kind of negatively charged ion to life system important.Human body is taken in an amount of fluorion can preventing dental caries, prevents osteoporosis.Yet excessive absorption fluorion can cause fluorosis, can cause bone generation fluorine osteosclerosis, sclerotin hardening, hyperosteogeny, makes the osteoarthrosis limitation of activity, even hunch, paralysis, completely loses work capacity.Therefore, the detection fluorion of quantitative and qualitative analysis is a very important problem.Generally, fluorion can by ion selective electrode and
19The F nuclear magnetic resonance, detects, but these methods all need expensive instrument and complicated test procedure.Developing conveniently Fluoride Analysis has been subject to people and has more and more paid close attention to.
At present people developed some can be in solution the sensor of colorimetric detection negatively charged ion.But colorimetric detection negatively charged ion in solution still needs obtain solution, and not Portable belt and preservation of solution.For this reason, if develop the novel material that to stablize the anionic colorimetric detection of depositing and being easy to carry about with one, preserving and using, using value will be arranged more.
Organogel be a kind of low-molecular-weight organic compound (gelator) in organic solvent by hydrogen bond, Van der Waals force,
π-πSupramolecule (soft) material that the weak interaction self-assembly forms between the accumulation equimolecular.This material has solid material and the distinctive advantage of fluent material simultaneously: gel molecular is keeping the chemical property of oneself, can carry out its some reactions in solution state, and gelatinous material has again the stability that is similar to solid simultaneously, as be easy to preserve etc.Therefore, detect soft material if develop based on the anionic colorimetric of organogel, be difficult for preservation, the problem such as Portable belt not in the time of will avoiding carrying out colorimetric detection with anion receptor solution.
Summary of the invention
The purpose of this invention is to provide a kind of acceptor compound---the 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.
Another object of the present invention provides a kind of synthetic method of this receptor compound.
A further object of the invention just provides the application of this receptor compound in the colorimetric detection fluorion.
The present invention more has a purpose, just provides a kind of organogel and the application in the colorimetric detection fluorion thereof of above-mentioned acceptor compound.
(1) acceptor compound
Acceptor compound of the present invention---5-(4-nitro) structural formula of phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone is as follows:
This receptor compound adopts the 5-(4-nitro) phenyl-2 furan carboxyaldehyde group is the signal reporter group, can make acceptor possess ability than colour discrimination; Adopt the acylhydrazone group as recognition site, make compound carry out combination with fluorion, therefore, can be used as acceptor compound for detection of the identification fluorion.
(2) acceptor compound is synthetic
Acceptor compound of the present invention---5-(4-nitro) synthetic method of phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone comprises following processing step:
(1) 5-dodecyloxy dimethyl isophthalate is synthetic: take methyl alcohol as reaction medium, with K
2CO
3As acid binding agent, KI makes lauryl bromide and 5-Hydroxy M Phthalic Acid dimethyl ester with the mol ratio of 1:0.5 ~ 1:2 as catalyzer, in 50 ~ 80 ℃ of back flow reaction 7 ~ 12h, separates out white solid and both gets;
Wherein the consumption of catalyzer KI is 0.1 ~ 0.01 times of lauryl bromide molar weight; Acid binding agent K
2CO
3Consumption and 5-Hydroxy M Phthalic Acid dimethyl ester equimolar amount.
(2) 5-dodecyloxy isopthalic dihydrazide is synthetic: take ethanol as reaction medium, make 5-dodecyloxy dimethyl isophthalate and hydrazine hydrate with the mol ratio of 1:2 ~ 1:10, in 60 ~ 90 ℃ of back flow reaction 4 ~ 10h, separate out white solid and both got;
(3) 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone is synthetic: take ethanol as reaction medium, making 5-dodecyloxy isopthalic dihydrazide and 5-(4-nitro) phenyl-2 furan carboxyaldehyde is with the mol ratio of 1:2 ~ 1:6, in 60 ~ 90 ℃ of back flow reaction 5 ~ 9h, separate out yellow solid, suction filtration, (volume ratio of ethanol and DMF is the recrystallization of 1:2 ~ 1:5), obtains target product with the mixed solution of ethanol and DMF.
The product that the present invention synthesizes detects through fusing point, nuclear magnetic resonance analyser, infrared spectra, ultimate analysis and UV spectrum, proves that target product synthesizes successfully.
(3) Anion Recognition of acceptor compound experiment
Pipette respectively the DMSO solution (2 * 10 of 0.5 mL main body L
-4MolL
-1) in a series of 10 mL colorimetric cylinders.Add respectively F
-, Cl
-, Br
-, I
-, CH
3COO
-, HSO
4 -, H
2PO
4 -, ClO
4 -DMSO solution (0.01mol/L) 0.5mL of the 4-butyl ammonium of negatively charged ion, be diluted to the 5mL scale with DMSO, making various anion concentrations is 50 times of acceptor density, mixing rear placement spends the night, in 25 ℃ of survey its uv-visible absorption spectras (DMSO makes reference), examine or check each acceptor to the response of negatively charged ion.
Found that, when at the DMSO of acceptor solution (2
10
-5M) add F in
-The DMSO solution (50eqv) of 4-butyl ammonium the time, significant variation has occured in the color of receptor solution: become redness from yellow; And the adding of other negatively charged ion has no significant effect the DMSO solution colour of acceptor.
Fig. 1 is that acceptor compound is in DMSO solution (2 * 10
-5MolL
-1) ultraviolet-visible spectrogram when interacting with various negatively charged ion (50eqv).As can be seen from Figure 1, in uv-vis spectra, F
-Adding make receptor solution corresponding absorption peak occur at the 510nm place.And the adding of other negatively charged ion has no significant effect the UV spectrum of the DMSO solution of acceptor.These phenomenons and presentation of results acceptor compound can colorimetric detection F in DMSO solution
-
Fig. 2 is F among the DMSO
-The absorption spectrum changing conditions of acceptor molecule when ion exists.Fig. 2 shows, in the DMSO of acceptor solution, adds gradually the F that concentration is 0.1 mol/L with the accumulation sampling system
-During the 4-butyl ammonium of ion, because acceptor molecule is subject to the perturbation of negatively charged ion, it is at one group of new absorption peak of 510 nm places appearance, and the corresponding increase of peak value, and 400 nm place absorbancys reduce gradually, and clearly isobestic point occurs at 440 nm places, show acceptor molecule and F
-Formed stable title complex.
According to F
-To the titration experiments (25 ℃ are utilized UV spectrum) of receptor solution, pass through 3S
B/ S calculates, and obtains this receptor to F
-The lowest detectable limit of ion reaches 3 * 10
-5Mol/L.
(4) organogel of acceptor compound
1, the preparation of the organogel of acceptor compound
Acceptor compound is joined in DMF, and heating makes its dissolving, and the formation mass percent is 1 ~ 1.5% solution, is cooled to room temperature, obtains the organogel of acceptor compound.
Detect by scanning electron microscope (SEM), find that there is (see figure 3) in this organogel with three-dimensional netted fiber attitude, can infer thus, acceptor compound of the present invention mainly is to be self-assembled into organogel by hydrogen bond, thereby this organogel has good thermostability.
2, the Anion Recognition performance of the organogel of acceptor compound
On white spot plate, get respectively 9 parts a small amount of
LOrganogel, and drip F at these organogels respectively
-, Cl
-, Br
-, I
-, Ac
-, H
2PO
4 -, HSO
4 -And ClO
4 -The DMSO solution (0.01mol/L) of the 4-butyl ammonium of negatively charged ion is observed the variation of organogel color.
Found that: organogel color when running into the DMSO solution of fluoride ion becomes redness by yellow; And when running into the solution that contains other ion, the organogel color is substantially constant.Therefore, but the fluorion in the single detection of this organogel colorimetric DMSO solution.
Utilize UV spectrum, according to F
-To the titration experiments of receptor solution, pass through 3S
B/ S calculates, and obtains this receptor to F
-The lowest detectable limit of ion reaches 3 * 10
-5Mol/L.
In sum, the present invention designs synthetic acceptor compound
,In DMSO solution, fluorion there is the colorimetric recognition capability.Acceptor compound is dissolved in the solution that is mixed with mass percent 1% ~ 1.5% among the DMF, be chilled to organogel that room temperature the forms fluorion in can colorimetric detection DMSO solution, and this organogel has good thermostability, is easy to carry, easy to use, detection sensitivity advantages of higher.
Description of drawings
Fig. 1 is that colorimetric detection fluorion acceptor compound is (2 * 10
-5MolL
-1) ultraviolet-visible spectrogram when in DMSO solution, interacting with various negatively charged ion (50eqv);
Fig. 2 is colorimetric detection fluorion acceptor compound (2 * 10
-5MolL
-1) in DMSO solution with F
-Ultraviolet spectra for titration figure;
Fig. 3 is the SEM figure (metal spraying is processed, ten thousand times of left Fig. 2, ten thousand times of right Fig. 5) of colorimetric detection fluorion acceptor compound organogel.
Embodiment
Embodiment one
1, acceptor compound is synthetic
In the 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 4.20g(20mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol add 2.76g(20mmol again) acid binding agent K
2CO
3, 0.07g(0.4mmol) KI is as catalyzer, is heated to 65 ℃, return stirring 10h; Separate out white solid M
1---5-dodecyloxy dimethyl isophthalate.
In the 50mL reaction flask, with M
13.78g(10mmol) be dissolved in the 30mL ethanol, add 1.50g(30mmol) hydrazine hydrate, be heated to 78 ℃, backflow 8h separates out white solid M
2---5-dodecyloxy isopthalic dihydrazide.
In the 50mL reaction flask, add 0.88g(4mmol) the 5-(4-nitro) phenyl-2 furan carboxyaldehyde, 0.76g(2mmol) M
2With 20mL ethanol, be heated to 78 ℃, return stirring 7h separates out yellow solid, suction filtration, usefulness ethanol-DMF(1:2(v/v)) recrystallization, and obtain acceptor compound---the 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.Yield is 82%.Its synthetic route is as follows:
The data illness that has not attacked the vital organs of the human body of synthetic product:
L. productive rate: 82%, m.p.〉300 ℃,
1H-NMR (DMSO-d
6, 400 MHz) δ 12.10 (s, 2H ,-NH), 8.44 (s, 2H ,=CH), 8.35-7.51 (m, 11H ,-ArH), 7.20 (d, 2H, HC=C), (7.19 d, 2H, C=CH), 4.13 (t, 2H ,-OCH
2), 1.78 (m, 2H ,-OCH
2CH
2), 1.46 (m, 2H ,-CH
2CH
3), 1.24 (m, 16H ,-C
8H
16), 0.84 (t, 3H ,-CH
2CH
3). IR (KBr, cm
-1)
v: 3446.51,1651.50,1598.91,1564.27,1517.69,1469.75,1333.22. MS(C
42H
44N
6O
9Calculated value),
M/z: 777.5 [M+H
+] (776.3).
2, the acceptor compound organogel is synthetic:
Take by weighing respectively some parts of the acceptor compound of 10mg, place respectively little reagent bottle, each adds 1 mL DMF, and heating makes its dissolving, forms respectively mass percent and be 1% DMF solution, be cooled to room temperature after, formed respectively stable organogel.
3, the acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds places on the white spot plate, and drips F at these organogels
-, Cl
-, Br
-, I
-, Ac
-, H
2PO
4 -, HSO
4 -And ClO
4 -The DMSO solution (0.01mol/L) of the 4-butyl ammonium of negatively charged ion.Acceptor body compound organogel contains F running into
-DMSO solution the time color become redness by yellow, when running into the DMSO solution of other ion, the organogel color is substantially constant.Therefore, the acceptor compound organogel can single selective identification fluorion.
Embodiment two
1, colorimetric detection fluorion acceptor compound is synthetic
In the 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 4.20g(20mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol add 2.76g(20mmol again) acid binding agent K
2CO
3, 0.03g(0.2mmol) KI is as catalyzer, is heated to 60 ℃, return stirring 4h; Separate out white solid M
1---5-dodecyloxy dimethyl isophthalate.
In the 50mL reaction flask, with M
13.78g(10mmol) be dissolved in the 30mL ethanol, add 1.00g(20mmol) hydrazine hydrate, be heated to 78 ℃, backflow 8h separates out white solid M
2---5-dodecyloxy isopthalic dihydrazide.
In the 50mL reaction flask, add 0.88g(4mmol) the 5-(4-nitro) phenyl-2 furan carboxyaldehyde, 0.76g(2mmol) M
2With 20mL ethanol, be heated to 60 ℃, return stirring 5h separates out yellow solid, suction filtration, usefulness ethanol-DMF(1:2(v/v)) recrystallization, and obtain acceptor compound---the 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.Yield is 64%.
2, the acceptor compound organogel is synthetic:
Take by weighing respectively some parts of the acceptor compound of 12mg, place respectively little reagent bottle, each adds 1 mL DMF, and heating makes its dissolving, forms respectively mass percent and be 1.2% DMF solution, be cooled to room temperature after, formed respectively stable organogel.
3, the acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds places on the white spot plate, and drips F at these organogels
-, Cl
-, Br
-, I
-, Ac
-, H
2PO
4 -, HSO
4 -And ClO
4 -The DMSO solution (0.01mol/L) of the 4-butyl ammonium of negatively charged ion.Acceptor body compound organogel contains F running into
-DMSO solution the time color become redness by yellow, when running into the DMSO solution of other ion, the organogel color is substantially constant.Therefore, the acceptor compound organogel can single selective identification fluorion.
Embodiment three
1, colorimetric detection fluorion acceptor compound is synthetic
In the 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 8.40g(40mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol add 2.76g acid binding agent K again
2CO
3, 0.13g(0.8mmol) KI is as catalyzer, is heated to 65 ℃, return stirring 10h; Separate out white solid M
1---5-dodecyloxy dimethyl isophthalate.
In the 50mL reaction flask, with M
13.78g(10mmol) be dissolved in the 30mL ethanol, add 4.50g(90mmol) hydrazine hydrate, be heated to 90 ℃, backflow 9h separates out white solid M
2---5-dodecyloxy isopthalic dihydrazide.
In the 50mL reaction flask, add 0.88g(4mmol) the 5-(4-nitro) phenyl-2 furan carboxyaldehyde, 0.76g(2mmol) M
2With 20mL ethanol, be heated to 90 ℃, return stirring 9h separates out yellow solid, suction filtration, usefulness ethanol-DMF(1:2(v/v)) recrystallization, and obtain acceptor compound---the 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.Yield is 73%.
2, the acceptor compound organogel is synthetic:
Take by weighing respectively some parts of the acceptor compound of 15mg, place respectively little reagent bottle, each adds 1 mL DMF, and heating makes its dissolving, forms respectively mass percent and be 1.5% DMF solution, be cooled to room temperature after, formed respectively stable organogel.
3, the acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds places on the white spot plate, and drips F at these organogels
-, Cl
-, Br
-, I
-, Ac
-, H
2PO
4 -, HSO
4 -And ClO
4 -The DMSO solution (0.01mol/L) of the 4-butyl ammonium of negatively charged ion.Acceptor body compound organogel contains F running into
-DMSO solution the time color become redness by yellow, when running into the DMSO solution of other ion, the organogel color is substantially constant.Therefore, the acceptor compound organogel can single selective identification fluorion.
Claims (10)
1. acceptor compound, its structural formula is as follows:
2. the synthetic method of acceptor compound as claimed in claim 1 comprises following processing step:
(1) 5-dodecyloxy dimethyl isophthalate is synthetic: take methyl alcohol as reaction medium, with K
2CO
3As acid binding agent, KI makes lauryl bromide and 5-Hydroxy M Phthalic Acid dimethyl ester with the mol ratio of 1:0.5 ~ 1:2 as catalyzer, in 50 ~ 80 ℃ of back flow reaction 7 ~ 12h, separates out white solid and both gets;
(2) 5-dodecyloxy isopthalic dihydrazide is synthetic: take ethanol as reaction medium, make 5-dodecyloxy dimethyl isophthalate and hydrazine hydrate with the mol ratio of 1:2 ~ 1:10, in 60 ~ 90 ℃ of back flow reaction 4 ~ 10h, separate out white solid and both got;
(3) 5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone is synthetic: take ethanol as reaction medium, making 5-dodecyloxy isopthalic dihydrazide and 5-(4-nitro) phenyl-2 furan carboxyaldehyde is with the mol ratio of 1:2 ~ 1:6, in 60 ~ 90 ℃ of back flow reaction 5 ~ 9h, separate out yellow solid, suction filtration, mixed solution recrystallization with ethanol and DMF obtains target product.
3. the synthetic method of acceptor compound as claimed in claim 2, it is characterized in that: the consumption of the described catalyzer KI of step (1) is 0.1 ~ 0.01 times of lauryl bromide molar weight.
4. the synthetic method of acceptor compound as claimed in claim 2 is characterized in that: the described acid binding agent K of step (1)
2CO
3Consumption and 5-Hydroxy M Phthalic Acid dimethyl ester equimolar amount.
5. the synthetic method of acceptor compound as claimed in claim 2, it is characterized in that: in the mixed solution of the described ethanol of step (3) and DMF, the volume ratio of ethanol and DMF is 1:2 ~ 1:5.
6. the as claimed in claim 1 application of acceptor compound in the colorimetric detection fluorion.
7. the as claimed in claim 6 application of acceptor compound in the colorimetric detection fluorion is characterized in that: in the DMSO of acceptor compound solution, and F
-Adding make the DMSO solution colour of acceptor compound become redness from yellow, and the adding of other negatively charged ion is right
LThe DMSO solution colour have no significant effect.
8. the as claimed in claim 6 application of acceptor compound in the colorimetric detection fluorion is characterized in that: in the DMSO of acceptor compound solution, and F
-Adding make the uv-vis spectra of the DMSO solution of acceptor compound corresponding absorption peak occur at the 510nm place, and the adding of other negatively charged ion has no significant effect the uv-vis spectra of the DMSO solution of acceptor compound.
9. the as claimed in claim 6 application of acceptor compound in the colorimetric detection fluorion, it is characterized in that: acceptor compound is joined in DMF, and heating makes its dissolving, and the formation mass percent is 1 ~ 1.5% solution, be cooled to room temperature, obtain the organogel of acceptor compound.
10. the as claimed in claim 9 application of acceptor compound in the colorimetric detection fluorion, it is characterized in that: the DMSO solution that drips the 4-butyl ammonium of negatively charged ion at the organogel of acceptor compound, when then the organogel of acceptor compound runs into the solution of fluoride ion, the organogel color becomes redness by yellow, and when running into the solution that contains other ion, the organogel color of acceptor compound is substantially constant.
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| CN107089925A (en) * | 2017-04-24 | 2017-08-25 | 兰州大学 | A kind of preparation method and application of chiral hydrazone compound and its rare earth compounding |
| CN107089925B (en) * | 2017-04-24 | 2019-08-30 | 兰州大学 | It is a kind of chirality hydrazone compound and its rare earth compounding preparation method and application |
| CN111848664A (en) * | 2020-07-15 | 2020-10-30 | 河西学院 | Receptor compound for colorimetric detection of fluoride ions, and preparation method and application thereof |
| CN112028866A (en) * | 2020-09-01 | 2020-12-04 | 贵州民族大学 | Hydrazone compound, preparation method thereof, ion recognition receptor and application |
| CN112538167A (en) * | 2020-12-03 | 2021-03-23 | 福州大学 | Alkyl chain modified acylhydrazone bond-linked covalent organic framework material and application thereof in photocatalytic hydrogen peroxide production |
| CN112538167B (en) * | 2020-12-03 | 2021-08-31 | 福州大学 | Alkyl chain modified acylhydrazone bond-linked covalent organic framework material and application thereof in photocatalytic hydrogen peroxide production |
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