CN109400634B - 2, 5-dihydroxy indium terephthalate complex, preparation method thereof and application of complex in fluorescence detection of hydrazine hydrate - Google Patents
2, 5-dihydroxy indium terephthalate complex, preparation method thereof and application of complex in fluorescence detection of hydrazine hydrate Download PDFInfo
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims abstract description 31
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 29
- JKQXBRSAIZITQO-UHFFFAOYSA-H [In+3].[In+3].[O-]C(=O)c1ccc(cc1)C([O-])=O.[O-]C(=O)c1ccc(cc1)C([O-])=O.[O-]C(=O)c1ccc(cc1)C([O-])=O Chemical compound [In+3].[In+3].[O-]C(=O)c1ccc(cc1)C([O-])=O.[O-]C(=O)c1ccc(cc1)C([O-])=O.[O-]C(=O)c1ccc(cc1)C([O-])=O JKQXBRSAIZITQO-UHFFFAOYSA-H 0.000 title claims abstract description 11
- 238000001917 fluorescence detection Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 6
- OYFRNYNHAZOYNF-UHFFFAOYSA-N H2dhybdc Natural products OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910001449 indium ion Inorganic materials 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- -1 indium 2, 5-dihydroxyterephthalate Chemical compound 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract description 9
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 3
- 229910052738 indium Inorganic materials 0.000 abstract description 2
- 238000004729 solvothermal method Methods 0.000 abstract description 2
- 238000001514 detection method Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012621 metal-organic framework Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
The invention discloses a 2, 5-dihydroxy indium terephthalate complex, a preparation method thereof and application of the complex In fluorescence detection of hydrazine2(DOBDC)2(OH)2Wherein the indium ion is trivalent and positive, DOBDC represents a divalent anion of 2, 5-dihydroxyterephthalic acid lacking the hydrogen atoms of the two carboxyl groups, and the hydroxyl group is monovalent and negative. The indium complex is prepared by taking 2, 5-dihydroxyterephthalic acid as a ligand and adopting a solvothermal method, has fluorescence property, can have good fluorescence quenching effect on hydrazine hydrate, has no response to ammonia water and hydroxylamine, can be used as a fluorescence sensor to detect hydrazine hydrate, and simultaneously eliminates the interference of the ammonia water and the hydroxylamine.
Description
Technical Field
The invention belongs to the technical field of indium-aromatic carboxylic acid metal organic complexes, and particularly relates to a 2, 5-dihydroxy indium terephthalate complex with fluorescent response to hydrazine hydrate and a preparation method of the complex.
Background
In recent years, metal-organic functional complexes have been a focus of attention of researchers because of their functions such as gas storage, molecular recognition, ion exchange, selective catalysis, gas adsorption, and fluorescence response. In the metal-organic functional complex, the indium-based metal-organic functional complex becomes an indispensable part of a metal-organic framework material family by virtue of unique structural characteristics, rich topological structure and wide application prospects in various fields, is widely concerned by researchers, and meanwhile, the metal-organic framework material constructed by taking trivalent metal indium ions as the center has higher thermodynamic stability, so that a foundation is laid for wide application.
Hydrazine is a colorless oily liquid with strong reducibility and toxicity, and has wide application in the industrial field. However, hydrazine is considered to be an extremely harmful substance to both the environment and the human body due to its polluting nature to the environment and carcinogenicity to the human body, and thus detection of hydrazine is an important study. Conventional hydrazine detection methods include titration, colorimetry, chromatography, and the like, but these methods have certain disadvantages such as time-consuming or low sensitivity.
Disclosure of Invention
The invention aims to provide an indium 2, 5-dihydroxyterephthalate complex with a fluorescence response to hydrazine hydrate and a preparation method of the complex.
For the above purpose, the indium 2, 5-dihydroxyterephthalate complex used In the present invention has In as a structural unit2(DOBDC)2(OH)2Wherein the indium ion is trivalent and positive, DOBDC represents a divalent anion of 2, 5-dihydroxyterephthalic acid deprived of hydrogen atoms on two carboxyl groups, and the hydroxyl group is monovalent and negative; which belongs to the orthorhombic system, Cmca space group, and the cell parameter a is
b is
c is
α is 90 °, β is 90 °, γ is 90 °.
The preparation method of the 2, 5-dihydroxy indium terephthalate complex comprises the following steps: adding 2, 5-dihydroxyterephthalic acid and indium chloride into a mixed solvent of N, N-dimethylformamide, water and isopropanol in a volume ratio of 1:1: 4-5 according to a molar ratio of 1: 1.5-2.5, ultrasonically dispersing uniformly, sealing, standing at a constant temperature of 80-85 ℃ for reacting for 2-4 days, and naturally cooling to room temperature to prepare the 2, 5-dihydroxyindium terephthalate complex.
The 2, 5-dihydroxy indium terephthalate complex can be used as a fluorescence sensor for fluorescence detection of hydrazine hydrate.
The invention takes 2, 5-dihydroxy terephthalic acid as a ligand, and prepares the 2, 5-dihydroxy indium terephthalate complex by a solvothermal method, and the wavelength corresponding to the maximum emission peak of the complex is 450 +/-2 nm. Meanwhile, the complex has high sensitivity to hydrazine hydrate, the fluorescence emission intensity of the complex is gradually reduced along with the increase of the concentration of the added hydrazine hydrate under the conditions that the excitation wavelength is 275nm and the slit width is 1.8nm, and the compound can be subjected to fluorescence quenching when the added hydrazine hydrate reaches a certain value; the sensitivity to ammonia water and hydroxylamine solution is not high, which shows that the complex can be used as a fluorescence sensor for distinguishing three hydrides of nitrogen to detect hydrazine hydrate, simultaneously eliminates the interference of ammonia water and hydroxylamine, has high detection sensitivity, and can reach the lowest detection limit of 1ppm to hydrazine hydrate.
Drawings
FIG. 1 is a crystal structure diagram of an indium 2, 5-dihydroxyterephthalate complex prepared in example 1.
FIG. 2 is a three-dimensional structural diagram of an indium 2, 5-dihydroxyterephthalate complex prepared in example 1.
FIG. 3 is a liquid fluorescence spectrum of indium 2, 5-dihydroxyterephthalate complex prepared in example 1 against hydrazine hydrate.
FIG. 4 is a liquid fluorescence spectrum of the indium 2, 5-dihydroxyterephthalate complex prepared in example 1 with respect to aqueous ammonia.
FIG. 5 is a liquid fluorescence spectrum of indium 2, 5-dihydroxyterephthalate complex prepared in example 1 versus hydroxylamine.
FIG. 6 is a graph of the color change of indium 2, 5-dihydroxyterephthalate complex prepared in example 1 as a function of hydrazine hydrate concentration.
Detailed Description
The present invention will be described in further detail with reference to the following drawings and examples, but the present invention is not limited to these examples.
Example 1
Adding 0.022g (0.1mmol) of indium chloride, 0.010g (0.05mmol) of 2, 5-dihydroxyterephthalic acid, 4mL of isopropanol, 1mL of distilled water and 1mL of N, N-dimethylformamide into a 20mL glass vial, carrying out ultrasonic treatment at room temperature for 30 minutes, sealing, standing at constant temperature of 85 ℃ for reaction for 3 days, naturally cooling to room temperature, filtering, washing with N-pentane for 3 times, blowing and drying in a nitrogen atmosphere to prepare the structural unit ofIn2(DOBDC)2(OH)2The indium 2, 5-dihydroxyterephthalate complex of (1) wherein the indium ion is trivalent and positive, DOBDC represents the divalent anion of 2, 5-dihydroxyterephthalic acid which has lost the hydrogen atoms at the two carboxyl groups, the hydroxyl group is monovalent and negative, the yield is 60.5%.
The single crystal structure of the prepared 2, 5-dihydroxy indium terephthalate complex is shown in figure 1, belongs to an orthorhombic system, Cmca space group and has a unit cell parameter a
b is
c is
α 90 DEG, β 90 DEG, gamma 90 DEG, 1 In being present In the individual units3+2 hydroxyl groups, 1 ligand of 2, 5-dihydroxyterephthalic acid, 2, 5-dihydroxyterephthalic acid loses hydrogen atoms on two carboxyl groups, carries two unit negative charges, has a hexacoordinate central In (III) atom, and coordinates with oxygen atoms O7 and O7a from water molecules and O2, O2a, O2b and O2c atoms from 2, 5-dihydroxyterephthalic acid respectively (bond lengths are respectively:
the key angles are respectively: o (7a) -In (1) -O (7) ═ 173.83(2) ° O (7a) -In (1) -O (1b) ═ 91.23(12) ° O (7) -In (1) -O (1b) ═ 93.20(11) ° O (7a) -In (1) -O (1) ═ 93.20(11) ° O (7) -In (1) -O (1) ═ 91.23(12) ° O (1b) -In (1) -O (1) ═ 88.2(2) ° O (7a) -In (1) -O (2c) ° 89.60(12) ° O7-In (1) -O (2c) ═ 85.81(11) ° O (1b) -In (1) -O (2c) ° 177.75(13) ° O (1) -In (1) -O (2c) ° O (93.17) ° O (1b) -In (1) -In (2c) ° O (17) O (7a) -In (1) -O (2d) 85.81(11 °), O (7) -In (1) -O (2d) 89.60(12 °),O(1b)-In(1)-O(2d)＝93.85(17)°、O(1)-In(1)-O(2d)＝177.75(13)°、O(2c)-In(1)-O(2d)＝84.1(2)°)。
The three-dimensional structure diagram of the prepared 2, 5-dihydroxy-terephthalic-acid indium complex is shown in fig. 2, indium ions form a one-dimensional indium chain in the structure, the indium chain is connected into a three-dimensional porous material through 2, 5-dihydroxy-terephthalic acid, and hydroxyl is distributed in a pore channel.
Example 2
Application of indium 2, 5-dihydroxyterephthalate complex of example 1 to fluorescence detection of hydrazine hydrate
Adding the 2, 5-dihydroxy indium terephthalate complex into N, N-dimethylformamide to prepare a complex solution with the mass-volume concentration of 1 mg/mL; and then adding hydrazine hydrate, ammonia water and hydroxylamine with different concentrations into the complex solution respectively, and performing fluorescence detection performance research on the hydrazine hydrate, the ammonia water and the hydroxylamine by using the 2, 5-dihydroxy indium terephthalate complex by using a PELS55 fluorescence spectrometer, wherein the result is shown in a figure 3-5.
As can be seen from FIG. 3, the maximum emission peak of the complex corresponds to a wavelength of 450. + -.2 nm. The fluorescence emission intensity of the complex gradually decreases with increasing concentration of hydrazine hydrate solution added at an excitation wavelength of 275nm and a slit width of 1.8 nm. When the concentration of the hydrazine hydrate solution added reached 5500ppm, the complex quenched fluorescence. The quenching rate K of the complex to hydrazine hydrate is calculated at the concentrationSV(KSV＝(I0-I)/I0(I0The fluorescence intensity of the system can be detected when no hydrazine hydrate is added, and I is the fluorescence intensity of the corresponding system when hydrazine hydrate with different concentrations is added) can reach 80.15 percent, and the lowest detection limit of the complex on hydrazine hydrate can reach 1ppm as can be seen from the figure. As can be seen from FIG. 4, under the same test conditions as those for detecting hydrazine hydrate, the fluorescence emission intensity of the complex is substantially constant with the increase in the concentration of the aqueous ammonia solution added, indicating that the complex is not responsive to aqueous ammonia. As can be seen from FIG. 5, under the same test conditions as those for detecting hydrazine hydrate, the fluorescence emission intensity of the complex remained substantially constant as the concentration of hydroxylamine solution was increased, indicating thatThe complex also did not respond to hydroxylamine. The experimental results show that the complex can be used as a fluorescence sensor for distinguishing three hydrides of nitrogen to detect hydrazine hydrate, and simultaneously eliminate the interference of ammonia and hydroxylamine. FIG. 6 shows the color change of the N, N-dimethylformamide solution of the complex, which is visible from the naked eye, as the concentration of the hydrazine hydrate solution increases, indicating that the complex has more convenient practical application in the detection of hydrazine hydrate.
Claims (2)
- Use of 2, 5-dihydroxy indium terephthalate complex with In structural unit In fluorescence detection of hydrazine hydrate2(DOBDC)2(OH)2In the formula, indium ions are positive and trivalent, DOBDC represents a divalent anion of 2, 5-dihydroxy terephthalic acid losing hydrogen atoms on two carboxyl groups, and hydroxyl is negative univalent, and belongs to an orthorhombic system, a Cmca space group, unit cell parameters a are 37.1792 Å, b are 23.4037 Å, c are 7.1550 Å and 90 degrees, β and gamma are 90 degrees.
- 2. Use of the indium 2, 5-dihydroxyterephthalate-based complex according to claim 1 for the fluorescence detection of hydrazine hydrate, characterized in that the complex is prepared by a method comprising: adding 2, 5-dihydroxyterephthalic acid and indium chloride into a mixed solvent of N, N-dimethylformamide, water and isopropanol in a volume ratio of 1:1: 4-5 according to a molar ratio of 1: 1.5-2.5, ultrasonically dispersing uniformly, sealing, standing at a constant temperature of 80-85 ℃ for reacting for 2-4 days, and naturally cooling to room temperature to prepare the 2, 5-dihydroxyindium terephthalate complex.
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