CN102942541B - 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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- CN102942541B CN102942541B CN201210511885.2A CN201210511885A CN102942541B CN 102942541 B CN102942541 B CN 102942541B CN 201210511885 A CN201210511885 A CN 201210511885A CN 102942541 B CN102942541 B CN 102942541B
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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 this receptor compound and do the application in 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, and the detection of negatively charged ion is also being become to a very necessary job, and therefore, design synthetic anionic sensor is more and more subject to investigator's attention.In Anion Recognition, main selectivity changes (colorimetric detection method) its solution colour after in conjunction with object negatively charged ion, because this method has, does not need valuable instrument, simple operation and other advantages, so obtained research very widely.Fluorion is a kind of negatively charged ion to life system important.Human body is taken in appropriate fluorion can preventing dental caries, prevents osteoporosis.Yet excessive absorption fluorion can cause fluorosis, can cause bone generation fluorine osteosclerosis, sclerotin hardening, hyperosteogeny, make osteoarthrosis limitation of activity, even hunch, paralysis, completely lose work capacity.Therefore, the detection fluorion of quantitative and qualitative analysis is a very important problem.Generally, fluorion can be by ion selective electrode and
19f 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 can stablize the anionic colorimetric detection of depositing and being easy to carry about with one, preserving and using, will more there is using value.
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 between accumulation equimolecular, weak interaction self-assembly forms.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, preserves etc. as being easy to.Therefore, if develop anionic colorimetric based on organogel, detect soft material, in the time of will avoiding carrying out colorimetric detection with anion receptor solution, be difficult for preservation, the problem such as Portable belt not.
Summary of the invention
The object of this invention is to provide a kind of acceptor compound---5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.
Another object of the present invention is to provide a kind of synthetic method of this receptor compound.
A further object of the invention, is just to provide the application of this receptor compound in colorimetric detection fluorion.
The present invention more has an object, is just to provide a kind of organogel and the application in 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 employing 5-(4-nitro) phenyl-2 furan carboxyaldehyde group is signal reporter group, can make acceptor possess the ability than colour discrimination; Adopt acylhydrazone group as recognition site, make compound carry out combination with fluorion, therefore, can be used as acceptor compound for detection of 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, as catalyzer, makes lauryl bromide and 5-Hydroxy M Phthalic Acid dimethyl ester with the mol ratio of 1:0.5 ~ 1:2, in 50 ~ 80 ℃ of back flow reaction 7 ~ 12h, separates out white solid and both obtains;
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 obtained;
(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 (volume ratio of ethanol and DMF is 1:2 ~ 1:5) recrystallization with ethanol and DMF, obtains target product.
The synthetic product of the present invention 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, with DMSO, be diluted to 5mL scale, 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 the response of each acceptor to negatively charged ion.
Found that, when the DMSO solution (2 at acceptor
10
-5m) in, add F
-the DMSO solution (50eqv) of 4-butyl ammonium time, having there is significant variation in the color of receptor solution: from yellow, has become redness; And 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 while interacting with various negatively charged ion (50eqv).As can be seen from Figure 1, in uv-vis spectra, F
-add and make receptor solution occur corresponding absorption peak at 510nm place.And 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 in DMSO
-the absorption spectrum changing conditions of acceptor molecule when ion exists.Fig. 2 demonstration, in the DMSO of acceptor solution, with accumulation sampling system, adding gradually concentration is the F of 0.1 mol/L
-during the 4-butyl ammonium of ion, because acceptor molecule is subject to the perturbation of negatively charged ion, there is one group of new absorption peak at 510 nm places in it, and the corresponding increase of peak value, and 400 nm place absorbancys reduce gradually, and there is isobestic point clearly at 440 nm places, show acceptor molecule and F
-formed stable title complex.
According to F
-to the titration experiments of receptor solution (25 ℃, utilize UV spectrum), 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 is dissolved it, and the solution that formation mass percent is 1 ~ 1.5%, is cooled to room temperature, obtains the organogel of acceptor compound.
By scanning electron microscope (SEM), detect, find that this organogel exists (see figure 3) with three-dimensional netted fiber state, can infer thus, acceptor compound of the present invention is to be mainly 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 on these organogels, drip F 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, observes the variation of organogel color.
Found that: organogel color when running into the DMSO solution of fluoride ion becomes redness from yellow; And while running into the solution containing other ion, organogel color is substantially constant.Therefore, this organogel can the single fluorion detecting in DMSO solution of colorimetric.
Utilize UV spectrum, according to F
-titration experiments to receptor solution, passes 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 is had to colorimetric recognition capability.Acceptor compound is dissolved in to the solution that is mixed with mass percent 1% ~ 1.5% in DMF, be chilled to the fluorion in the organogel energy colorimetric detection DMSO solution that room temperature forms, and this organogel has good thermostability, be easy to carry, easy to use, detection sensitivity advantages of higher.
Accompanying drawing explanation
Fig. 1 is that colorimetric detection fluorion acceptor compound is (2 * 10
-5molL
-1) ultraviolet-visible spectrogram while interacting with various negatively charged ion (50eqv) in DMSO solution;
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 mono-
1, acceptor compound is synthetic
In 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 4.20g(20mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol, then add 2.76g(20mmol) 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 50mL reaction flask, by M
13.78g(10mmol) be dissolved in 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 50mL reaction flask, add 0.88g(4mmol) 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, with ethanol-DMF(1:2(v/v)) recrystallization, obtain acceptor compound---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: 300 ℃ of 82%, m.p. >,
1h-NMR (DMSO-d
6, 400 MHz) and 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, acceptor compound organogel is synthetic:
Take respectively some parts of the acceptor compound of 10mg, be placed in respectively little reagent bottle, respectively add 1 mL DMF, heating is dissolved it, forms respectively mass percent and be 1% DMF solution, is cooled to after room temperature, has formed respectively stable organogel.
3, acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds is placed on white spot plate, and drips F on 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 is running into containing F
-dMSO solution time color from yellow, become redness, when running into the DMSO solution of other ion, organogel color is substantially constant.Therefore, acceptor compound organogel energy single selective identification fluorion.
Embodiment bis-
1, colorimetric detection fluorion acceptor compound is synthetic
In 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 4.20g(20mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol, then add 2.76g(20mmol) 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 50mL reaction flask, by M
13.78g(10mmol) be dissolved in 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 50mL reaction flask, add 0.88g(4mmol) 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, with ethanol-DMF(1:2(v/v)) recrystallization, obtain acceptor compound---5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.Yield is 64%.
2, acceptor compound organogel is synthetic:
Take respectively some parts of the acceptor compound of 12mg, be placed in respectively little reagent bottle, respectively add 1 mL DMF, heating is dissolved it, forms respectively mass percent and be 1.2% DMF solution, is cooled to after room temperature, has formed respectively stable organogel.
3, acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds is placed on white spot plate, and drips F on 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 is running into containing F
-dMSO solution time color from yellow, become redness, when running into the DMSO solution of other ion, organogel color is substantially constant.Therefore, acceptor compound organogel energy single selective identification fluorion.
Embodiment tri-
1, colorimetric detection fluorion acceptor compound is synthetic
In 50mL reaction flask, add 4.96g(20mmol) lauryl bromide, 8.40g(40mmol) 5-Hydroxy M Phthalic Acid dimethyl ester and 50mL methyl alcohol, then add 2.76g acid binding agent K
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 50mL reaction flask, by M
13.78g(10mmol) be dissolved in 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 50mL reaction flask, add 0.88g(4mmol) 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, with ethanol-DMF(1:2(v/v)) recrystallization, obtain acceptor compound---5-(4-nitro) phenyl-2 furan carboxyaldehyde-5-dodecyloxy isophthaloyl hydrazone.Yield is 73%.
2, acceptor compound organogel is synthetic:
Take respectively some parts of the acceptor compound of 15mg, be placed in respectively little reagent bottle, respectively add 1 mL DMF, heating is dissolved it, forms respectively mass percent and be 1.5% DMF solution, is cooled to after room temperature, has formed respectively stable organogel.
3, acceptor compound organogel detects identification F
-
The organogel of getting 9 parts of acceptor compounds is placed on white spot plate, and drips F on 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 is running into containing F
-dMSO solution time color from yellow, become redness, when running into the DMSO solution of other ion, organogel color is substantially constant.Therefore, acceptor compound organogel energy single selective identification fluorion.
Claims (10)
1. an 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, as catalyzer, makes lauryl bromide and 5-Hydroxy M Phthalic Acid dimethyl ester with the mol ratio of 1:0.5 ~ 1:2, in 50 ~ 80 ℃ of back flow reaction 7 ~ 12h, separates out white solid and get final product;
(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 get final product;
(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, 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, 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 application of acceptor compound in colorimetric detection fluorion as claimed in claim 1.
7. the application of acceptor compound in colorimetric detection fluorion as claimed in claim 6, is characterized in that: in the DMSO of acceptor compound solution, and F
-add and make the DMSO solution colour of acceptor compound become redness from yellow, and Cl
-, Br
-, I
-, CH
3cOO
-, HSO
4 -, H
2pO
4 -, ClO
4 -add the DMSO solution colour of acceptor compound had no significant effect.
8. the application of acceptor compound in colorimetric detection fluorion as claimed in claim 6, is characterized in that: in the DMSO of acceptor compound solution, and F
-the uv-vis spectra that adds the DMSO solution that makes acceptor compound at 510nm place, there is corresponding absorption peak, and Cl
-, Br
-, I
-, CH
3cOO
-, HSO
4 -, H
2pO
4 -, ClO
4 -add the uv-vis spectra of the DMSO solution of acceptor compound had no significant effect.
9. the application of acceptor compound in colorimetric detection fluorion as claimed in claim 6, it is characterized in that: acceptor compound is joined in DMF, and heating is dissolved it, the solution that formation mass percent is 1 ~ 1.5%, be cooled to room temperature, obtain the organogel of acceptor compound.
10. the application of acceptor compound in colorimetric detection fluorion as claimed in claim 9, it is characterized in that: the DMSO solution that drips the 4-butyl ammonium of negatively charged ion on the organogel of acceptor compound, when the organogel of acceptor compound runs into the solution of fluoride ion, organogel color becomes redness from yellow, and runs into containing Cl
-, Br
-, I
-, CH
3cOO
-, HSO
4 -, H
2pO
4 -, ClO
4 -solution time, the organogel color of acceptor compound is substantially constant.
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| CN104119303B (en) * | 2014-03-06 | 2015-12-09 | 西北师范大学 | The acceptor compound of colorimetric-fluorescence two channels identification mercury ion and Synthesis and applications thereof |
| CN104193706B (en) * | 2014-04-30 | 2015-10-28 | 西北师范大学 | A kind of based on not alkali and the preparation and detecting the application in mercury ion as acceptor molecule of the bilateral west of 1,5-diaminonaphthalene |
| CN104829487B (en) * | 2015-03-27 | 2016-09-07 | 福州大学 | Assemble ammonia sensitized metal-organogel Composite soft material material and the preparation thereof of luminescence enhancement |
| CN104987299A (en) * | 2015-05-08 | 2015-10-21 | 西北师范大学 | Fluorinion receptor compound, synthesis method thereof, and application thereof in colorimetric and fluorescent two-way identification of fluorinions |
| 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 |
| 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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