CN113402449A - Compound for rapidly detecting zinc ions and preparation method thereof - Google Patents
Compound for rapidly detecting zinc ions and preparation method thereof Download PDFInfo
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- CN113402449A CN113402449A CN202110688970.5A CN202110688970A CN113402449A CN 113402449 A CN113402449 A CN 113402449A CN 202110688970 A CN202110688970 A CN 202110688970A CN 113402449 A CN113402449 A CN 113402449A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title abstract description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000007787 solid Substances 0.000 claims abstract description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000001514 detection method Methods 0.000 claims abstract description 31
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- KXZQYLBVMZGIKC-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CNCC1=CC=CC=N1 KXZQYLBVMZGIKC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 12
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 claims abstract description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 4
- DNKGFGZIVLXWOY-UHFFFAOYSA-N n-[[10-[[bis(pyridin-2-ylmethyl)amino]methyl]anthracen-9-yl]methyl]-1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1C2=CC=CC=C2C(CN(CC=2N=CC=CC=2)CC=2N=CC=CC=2)=C2C=CC=CC2=1)CC1=CC=CC=N1 DNKGFGZIVLXWOY-UHFFFAOYSA-N 0.000 claims 1
- 238000002189 fluorescence spectrum Methods 0.000 abstract description 8
- 239000000523 sample Substances 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 4
- 230000008499 blood brain barrier function Effects 0.000 abstract description 3
- 210000001218 blood-brain barrier Anatomy 0.000 abstract description 3
- 238000010171 animal model Methods 0.000 abstract description 2
- 238000003384 imaging method Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000012795 verification Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 1,3, 5-trioxymethylene, N, N, N-trimethyl-1-tetradecyl ammonium bromide Chemical class 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000036559 skin health Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 1
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a compound for rapidly detecting zinc ions and a preparation method thereof. The preparation method of the compound comprises the following steps: dissolving anthracene in acetic acid solution of hydrogen bromide; adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide for reaction to obtain yellow solid; adding bis (2-pyridylmethyl) amine and triethylamine, dissolving in tetrahydrofuran, and reacting. The compound prepared by the invention can break through blood brain barrier through animal model and living body imaging verification, and is expected to be used as a reliable depression detection probe. The invention utilizes the fluorescence spectrum technology for detection, has simple method and wide detection range, and can be used in a plurality of different fields. The compound prepared by the invention realizes better selectivity to zinc ions in an organic solvent environment, and is not easy to interfere; the lower detection limit is low, and trace zinc ions can be detected; has high sensitivity and high selectivity.
Description
Technical Field
The invention relates to the technical field of supermolecule chemistry, in particular to a compound for rapidly detecting zinc ions and a preparation method thereof.
Background
The zinc ion has important significance for maintaining biological functions, and the zinc ion directly participates in enzyme synthesis, and has multiple important functions of promoting the growth and development of organisms and tissue regeneration, protecting skin health, maintaining immune functions and the like. However, the environment in animals and human bodies is very complex, and the influence of factors such as blood brain barrier and the like exists, so that the method for properly measuring zinc ions is few. At present, the zinc ion content of a human body is generally measured by an atomic absorption detection method for taking blood samples or hair, or a gas chromatography; the two methods have the problems of low speed, poor selectivity, low result sensitivity, high cost and the like.
Disclosure of Invention
The invention aims to provide a compound for rapidly detecting zinc ions and a preparation method thereof, and the compound has the advantages of high detection speed, high selectivity, high sensitivity and low cost when being used for detecting the zinc ions.
The first purpose of the invention is realized by the following technical scheme that the compound for rapidly detecting the zinc ions has the following structural formula:
the second purpose of the invention is realized by the following technical scheme:
a preparation method of a compound for rapidly detecting zinc ions comprises the following steps:
(1) dissolving anthracene in acetic acid solution of hydrogen bromide;
(2) adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide into the system obtained in the step (1) for reaction to obtain yellow solid;
(3) and (3) dissolving the yellow solid obtained in the step (2), bis (2-pyridylmethyl) amine and triethylamine in tetrahydrofuran to react, and using the compound for rapidly detecting zinc ions.
Preferably, in the step (1), the mass ratio of the acetic acid solution of anthracene to hydrogen bromide is 10:298, and the volume ratio of hydrogen bromide to acetic acid in the acetic acid solution of hydrogen bromide is 4: 1.
Preferably, in the step (2), the mass ratio of anthracene, 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecylammonium bromide is 25:25: 1.
Preferably, in the step (2), the yellow solid is washed with ethanol.
Preferably, the reaction temperature of the step (2) is 80-90 ℃, and the reaction time is 18-24 h.
Preferably, the reaction temperature of the step (3) is 25-30 ℃, and the reaction time is 3-5 h.
Preferably, in the step (3), the mass ratio of the yellow solid to the bis (2-pyridylmethyl) amine is 5:2, and the mass ratio of triethylamine to the bis (2-pyridylmethyl) amine is 5: 1.
The invention has the following advantages:
(1) the compound prepared by the invention can break through blood brain barrier through animal model and living body imaging verification, shows good detection signals under complex biological background in brain, and is expected to be used as a reliable depression detection probe.
(2) The invention utilizes the fluorescence spectrum technology for detection, the method is simple, and the identification process does not need pretreatment operation; the detection range is wide, and the method can be used in a plurality of different fields such as in vivo detection, environmental detection and the like.
(3) The compound prepared by the invention realizes better selectivity to zinc ions in an organic solvent environment, and is not easy to interfere; the lower detection limit is low, and trace (ppm level) zinc ions can be detected; in the experiment, zinc ions are added in a trace amount, so the experiment has high sensitivity and high selectivity.
(4) The preparation raw materials of the invention are anthracene, 1,3, 5-trioxymethylene, N, N, N-trimethyl-1-tetradecyl ammonium bromide and the like, and the raw materials have low price; and the synthesis route is simple, the reaction condition is mild, and no by-product is generated.
Drawings
FIG. 1 is a structural formula of a target compound of the present invention;
FIG. 2 is a reaction scheme for the synthesis of a target compound according to the present invention;
FIG. 3 is a drawing showing the preparation of a target compound of the present invention1H NMR chart;
FIG. 4 shows a compound of interest according to the present invention13C NMR chart;
FIG. 5 is a fluorescence spectrum of molecular recognition of a target compound of the present invention with zinc ion as a guest, where Blank (i.e., 0 in the figure) represents the fluorescence spectrum of the target compound without zinc ion, and 0.2ml of the target compound is added to a cuvette at a concentration of 1X 10-5The fluorescence spectrum scanning of the zinc ion solution of mol/L is carried out nine times to obtain a spectrum curve with the equivalent weight of 0-9, and the figure shows that the fluorescence intensity is continuously enhanced along with the enhancement of the zinc ion concentration.
Detailed Description
The technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. The drawings are only for purposes of illustration and are not intended to be limiting, and are merely schematic and non-limiting. For those skilled in the art to which the invention pertains, several simple deductions or substitutions can be made without departing from the spirit of the invention, and all shall be considered as belonging to the protection scope of the invention.
EXAMPLE 1 preparation of the object Compound
The preparation method of the target compound for detecting the zinc ions is shown in figure 2, and specifically comprises the following steps:
step (1): anthracene was dissolved in hydrogen bromide in acetic acid. The volume ratio of hydrogen bromide to acetic acid is 4: 1.
Step (2): adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide into the system in the step (1), and stirring and reacting at the temperature of 80-90 ℃ for 18-24 h; take yellow solid.
The mass ratio of anthracene to 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide is 25:25: 1.
And (3): and (3) carrying out suction filtration on the yellow solid precipitated in the step (2) by using a Buchner funnel, and washing filter residues by using ethanol to obtain a light yellow solid.
And (4): dissolving the yellow solid obtained in the step (3), bis (2-pyridylmethyl) amine and triethylamine in tetrahydrofuran to react for 3h, wherein the mass ratio of the yellow solid to the bis (2-pyridylmethyl) amine is 5: 2.
and (5): gradually precipitating the reaction in the step (4) to obtain a yellow solid; and (3) completely carrying out rotary evaporation on the solvent by using a rotary evaporator at the temperature of 38-39 ℃, the pressure of 160-180r/min and the pressure of 0.08MPa to obtain a yellow solid.
And (6): stirring the yellow solid obtained by the reaction in the step (5) with ethyl acetate and silica gel, filling the mixture into a column, passing through a chromatographic column (the ground opening of the Xinweier company is 24/40), removing impurity points, wherein the solvent for stirring the sample is ethyl acetate, the solvent for passing through the column is a mixed solvent consisting of methanol and ethyl acetate, the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:10, the impurity points are removed, and the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:5 for a target compound for zinc ion detection.
The structure of the target compound is shown in figure 1, and the yield is 12.5%.
Performing nuclear magnetic resonance detection on the target compound,1h NMR and13the results of C NMR measurements are shown in FIGS. 3 and 4, respectively; the nuclear magnetic resonance results are as follows:
m.p:165.4-166.5℃.1H NMR(500MHz,CDCl3)δ8.44(d,J＝4.7Hz,8H),8.40(d,J＝9.5Hz,4H),7.52(t,J＝7.6Hz,4H),7.42(d,J＝9.3Hz,4H),7.29(d,J＝7.8Hz,4H),7.09–6.99(m,4H),4.63(s,1H),3.87(s,8H).13C NMR(126MHz,CDCl3)δ159.7,148.7,136.1,131.1,130.5,125.5,124.9,123.5,121.9。
example 2 Rapid detection method for Zinc ions
Step (1): the target compound obtained in example 1 was used as a detection reagent (solute) with a solvent of acetonitrile to water in a volume ratio of 1:1, and the amount concentration of the prepared substance was 5X 10-5A solution of mol/L was used as a detection solution.
Zinc sulfate heptahydrate is used as zinc ion source (solute), acetonitrile and water are used as solvent in the volume ratio of 1:1, and the quantity concentration of the prepared material is 1 x 10-5mol/L solution.
Step (2): adding the detection solution prepared in the step (1) into a fluorescent sample cell (2ml) by using a molecular fluorescence method, and gradually dropwise adding zinc ions with the concentration of 1 multiplied by 10-5And (3) matching zinc ions with the detection solution by using the mol/L solution, and observing the change of the fluorescence intensity along with the gradual addition of the zinc ion solution. The emission spectrum of molecular fluorescence is selected at EXThe scanning speed is 1500nm/min between 250 and 270nm, the fluorescence spectrum scanning is faster than the gas chromatography analysis, the result is sensitive, and the selectivity is good.
As a result, as shown in FIG. 5, Blank shows the fluorescence spectrum of the objective compound in the absence of added zinc ion, and 0.2ml of 1X 10 solution was added to each cuvette-5And (3) carrying out fluorescence spectrum scanning on the zinc ion solution of mol/L for nine times to obtain a spectrum curve with the equivalent weight of 0-9, wherein the fluorescence intensity of the target compound is continuously enhanced along with the increase of the zinc ion solution.
EXAMPLE 3 preparation of the object Compound
The preparation method of the target compound for detecting the zinc ions is shown in figure 2, and specifically comprises the following steps:
step (1): anthracene was dissolved in hydrogen bromide in acetic acid.
The volume ratio of hydrogen bromide to acetic acid is 4:1, and the mass of acetic acid is 6 times that of anthracene.
Step (2): adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide into the system in the step (1), and stirring and reacting for 24 hours at the temperature of 80 ℃; take yellow solid.
The mass ratio of anthracene to 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide is 25:25: 1.
And (3): and (3) carrying out suction filtration on the yellow solid precipitated in the step (2) by using a Buchner funnel, and washing filter residues by using ethanol to obtain a light yellow solid.
And (4): dissolving the yellow solid obtained in the step (3), bis (2-pyridylmethyl) amine and triethylamine in tetrahydrofuran to react for 5h, wherein the mass ratio of the yellow solid to the bis (2-pyridylmethyl) amine is 5: 2.
And (5): gradually precipitating the reaction in the step (4) to obtain a yellow solid; and (3) completely carrying out rotary evaporation on the solvent by using a rotary evaporator at the temperature of 38-39 ℃, the pressure of 160-180r/min and the pressure of 0.08MPa to obtain a yellow solid.
And (6): stirring the yellow solid obtained by the reaction in the step (5) with ethyl acetate and silica gel, filling the mixture into a column, passing through a chromatographic column (the ground opening of the Xinweier company is 24/40), removing impurity points, wherein the solvent for stirring the sample is ethyl acetate, the solvent for passing through the column is a mixed solvent consisting of methanol and ethyl acetate, the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:15, the impurity points are removed, and the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:10 for a target compound for zinc ion detection.
The structure of the target compound is shown in figure 1, and the yield is 13.5%.
The nuclear magnetic resonance detection of the target compound was performed, and the result was the same as in example 1.
EXAMPLE 4 preparation of the object Compound
The preparation method of the target compound for detecting the zinc ions is shown in figure 2, and specifically comprises the following steps:
step (1): anthracene was dissolved in hydrogen bromide in acetic acid.
The volume ratio of hydrogen bromide to acetic acid is 4:1, and the mass of acetic acid is 5.5 times that of anthracene.
Step (2): adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide into the system in the step (1), and stirring and reacting for 22 hours at the temperature of 80 ℃; take yellow solid.
The mass ratio of anthracene to 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide is 23:25: 1.
And (3): and (3) carrying out suction filtration on the yellow solid precipitated in the step (2) by using a Buchner funnel, and washing filter residues by using ethanol to obtain a light yellow solid.
And (4): dissolving the yellow solid obtained in the step (3), bis (2-pyridylmethyl) amine and triethylamine in tetrahydrofuran to react for 4h, wherein the mass ratio of the yellow solid to the bis (2-pyridylmethyl) amine is 3: 1.
And (5): gradually precipitating the reaction in the step (4) to obtain a yellow solid; and (3) completely carrying out rotary evaporation on the solvent by using a rotary evaporator at the temperature of 38-39 ℃, the pressure of 160-180r/min and the pressure of 0.08MPa to obtain a yellow solid.
And (6): stirring the yellow solid obtained by the reaction in the step (5) with ethyl acetate and silica gel, filling the mixture into a column, passing through a chromatographic column (the ground opening of the Xinweier company is 24/40), removing impurity points, wherein the solvent for stirring the sample is ethyl acetate, the solvent for passing through the column is a mixed solvent consisting of methanol and ethyl acetate, the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:30, the impurity points are removed, and the volume ratio of the ethyl acetate to the solvent for passing through the column is 1:15 for a target compound for zinc ion detection.
The structure of the target compound is shown in figure 1, and the yield is 15.1%.
The nuclear magnetic resonance detection of the target compound was performed, and the result was the same as in example 1.
Claims (8)
1. A compound for rapidly detecting zinc ions, which is characterized in that the system is named as 9, 10-bis [ bis (2-picolyl) aminomethyl ] anthracene, and the structural formula is as follows:
2. the method for preparing a compound for rapid detection of zinc ions according to claim 1, comprising the steps of:
(1) dissolving anthracene in acetic acid solution of hydrogen bromide;
(2) adding 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide into the system obtained in the step (1) for reaction to obtain yellow solid;
(3) and (3) dissolving the yellow solid obtained in the step (2), bis (2-pyridylmethyl) amine and triethylamine in tetrahydrofuran to react, and using the compound for rapidly detecting zinc ions.
3. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: in the step (1), the mass ratio of anthracene to hydrogen bromide is 10:298, and the volume ratio of hydrogen bromide to acetic acid in an acetic acid solution of hydrogen bromide is 4: 1.
4. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: in the step (2), the mass ratio of anthracene, 1,3, 5-trioxymethylene and N, N, N-trimethyl-1-tetradecyl ammonium bromide is 25:25:1-15:15: 6.
5. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: in the step (2), the yellow solid is washed by ethanol.
6. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: the reaction temperature of the step (2) is 80-90 ℃, and the reaction time is 18-24 h.
7. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: the reaction temperature of the step (3) is 25-30 ℃, and the reaction time is 3-5 h.
8. The method for preparing a compound for rapid detection of zinc ions according to claim 2, wherein: in the step (3), the mass ratio of the yellow solid to the bis (2-pyridylmethyl) amine is 5:2-3:1, and the mass ratio of the triethylamine to the bis (2-pyridylmethyl) amine is 3:1-5: 1.
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