CN114507355B - Zinc-based triazole luminescent material and preparation method and application thereof - Google Patents
Zinc-based triazole luminescent material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a zinc-based triazole luminescent material, a preparation method and application thereof, wherein the chemical formula of the minimum asymmetric unit of the zinc-based triazole luminescent material is as follows: [ Zn ] 3 (BTA) 2 (5‑tbuip) 2 ]Mixing zinc nitrate hexahydrate, BTA and 5-tert-butyl isophthalic acid according to a proportion, adding acetonitrile and water, stirring, filling into a high-temperature-resistant glass bottle, reacting at 100 to 120 ℃ for 2~3 days, slowly cooling to room temperature, and filtering to obtain a colorless rod-shaped crystal, namely the zinc-based triazole luminescent material. The luminescent material has high fluorescence quantum yield and has potential application value in the fields of light-emitting diodes, biological imaging, fluorescence detection and the like. Metal-organic framework material with excellent fluorescence characteristics for Fe 3+ Exhibits rapid and efficient fluorescence detection performance.
Description
Technical Field
The invention belongs to the field of luminescent metal organic framework materials, relates to a zinc-based triazole luminescent material, and a preparation method and application thereof, and particularly relates to a zinc-based triazole luminescent material which takes benzotriazole as a main ligand, 5-tert-butyl isophthalic acid as an auxiliary ligand, and Zn 2+ A metal organic framework material formed by self-assembly, a preparation method thereof and application in the aspect of utilizing the fluorescence characteristic of the compound.
Background
Metal-organic frameworks (MOFs) are also called coordination polymers, are a class of crystalline materials formed by self-assembly of organic ligands and Metal centers and have one-dimensional, two-dimensional and three-dimensional infinite network structures, and have the rigidity of inorganic materials and the flexibility of organic materials, so that the Metal-organic frameworks (MOFs) present huge development potential and attractive development prospects in the aspect of modern material research.
Iron element is the most abundant trace element in human body and is important in many physiological processes, and abnormal iron concentration can cause anemia and blood colorPigmentation, liver damage, etc. Further, fe 3+ As one of the main sources of industrial process contaminants, pollution of the ecological environment occurs. To date, most methods for identifying toxic metal ions have been based primarily on instrumental methods, including atomic absorption spectroscopy, ICP-MS, and electrochemical analysis. However, these methods have some disadvantages, such as time consuming, expensive, difficult to maneuver, and the need for trained personnel. Therefore, it is urgently required to realize the effect on Fe 3+ The rapid and highly selective detection is important.
In recent years, fluorescent probes are widely used for detecting toxic pollutants such as inorganic heavy metal ions, toxic anions and small organic molecules due to strong operability, low cost and excellent response performance. Compared with expensive and precise instruments, the fluorescent probe has the advantages of low cost, portability, precision, real-time detection and the like when used for detecting chemical pollutants. Fluorescence detection provides a selective detection of Fe 3+ Simple method of ion. These metal ions are widely present in water, fluorescence detection is not affected by other metal ions in water, and the material needs to maintain its porous characteristics and high absorption capacity. Therefore, it is a challenge how to develop materials having these characteristics.
Due to the increasing population, together with the continuous development of urbanization and industrialization, the emission of various pollutants faces unprecedented pressure to the global environment. Therefore, there is an increasing demand for identifying and continuously monitoring chemical components in the environment, and the development of efficient chemical sensors is crucial to the monitoring and identification of environmental pollutants. The luminescent metal organic framework material has the comprehensive characteristics of both inorganic and organic, but the development of the synergistic effect of the physical and chemical properties of the inorganic and organic parts makes the material more diversified in property and increasingly difficult to obtain the material with the characteristics of a nano-pore structure, high porosity, large internal specific surface area and the like.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to solve the technical problem of providing a zinc-based triazole luminescent material. The invention carries out self-assembly by taking metal ions and functionalized benzotriazole as main ligandsThe metal organic framework material (Zn-MOF) with excellent fluorescence characteristic is constructed by the effect of the assembly, and the metal organic framework material is used for treating Fe 3+ Exhibits rapid and efficient fluorescence detection performance.
The invention also aims to solve the technical problem of providing a preparation method of the zinc-based triazole luminescent material. The invention selects the benzotriazole which has low price and multiple potential coordination modes, can provide dynamic and flexible frameworks as a main ligand, is used as a rigid polyfunctional group ligand and has a larger benzene ring and triazole ring conjugated system. Benzotriazole is taken as a main ligand, 5-tert-butyl isophthalic acid is taken as an auxiliary ligand and zinc nitrate hexahydrate are synthesized by a solvothermal method, and the formed rigid framework structure limits the rotation and vibration of an organic ligand, so that the fluorescence luminous efficiency is improved.
The invention also aims to solve the technical problem of providing the application of the zinc-based triazole luminescent material.
The technical problem to be solved by the invention is to provide a fluorescent probe for detecting Fe 3+ The fluorescent probe of (1).
The invention finally solves the technical problem of providing Fe 3+ The method of (1).
The invention selects the benzotriazole which has low price and multiple potential coordination modes, can provide dynamic and flexible frameworks as a main ligand, is used as a rigid polyfunctional group ligand and has a larger benzene ring and triazole ring conjugated system. Benzotriazole is taken as a main ligand, 5-tert-butyl isophthalic acid is taken as an auxiliary ligand and zinc nitrate hexahydrate are synthesized by a solvothermal method, and the formed rigid framework structure limits the rotation and vibration of the organic ligand, so that the fluorescence luminous efficiency is improved.
The technical scheme is as follows: the invention provides a zinc-based triazole luminescent material, and zincThe chemical formula of the minimum asymmetric unit of the triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Wherein BTA represents benzotriazole, 5-tbuip represents 5-tert-butylisophthalic acid, [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]The structural formula is as follows:
wherein BTA represents benzotriazole, and the structural formula is shown as follows:
the zinc-based triazole luminescent material has the excitation wavelength of 300-320 nm and the emission wavelength of 320-350 nm.
The invention also discloses a three-dimensional frame structure with the minimum asymmetric unit of [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Single crystal data of the complex of (1). The minimum asymmetric unit can be infinitely stacked, and the structural formula of the zinc-based luminescent metal organic framework material can be [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ] n And n is a natural number.
The invention also discloses a preparation method of the zinc-based triazole luminescent material, which comprises the following steps: weighing a certain proportion of zinc nitrate hexahydrate, benzotriazole and 5-tert-butyl isophthalic acid, adding into a reaction container, adding a proper amount of acetonitrile and water, ultrasonically dissolving until the solution becomes clear, placing into a constant-temperature drying oven, reacting for 2-3 days at 100-120 ℃, naturally cooling to room temperature, and filtering to obtain colorless rod-shaped crystals, thus obtaining the zinc-based triazole luminescent material.
The rigid framework structure formed by the zinc-based triazole luminescent material limits rotation and vibration of the organic ligand, so that the luminescent efficiency of fluorescence is improved, and the metal organic framework material has high fluorescence quantum yield.
Wherein the molar ratio of the zinc nitrate hexahydrate, the benzotriazole and the 5-tert-butyl isophthalic acid is 3: 2: 1.
Wherein the volume ratio of the acetonitrile to the water is 2: 1.
The invention also comprises the application of the zinc-based triazole luminescent material in the preparation of a light-emitting diode, or biological imaging or fluorescence detection.
The invention also comprises a fluorescent probe which is made of the zinc-based triazole luminescent material.
Wherein the fluorescent probe is used for detecting Fe 3+ The fluorescent probe of (1).
Wherein, the Fe 3+ Quenching constant K of sv Reach 8.4X 10 3 M -1 。
The invention also comprises Fe 3+ The detection method of ions adopts the zinc-based triazole luminescent material or the fluorescent probe to detect Fe 3+ The solution of ions is detected.
Has the advantages that: compared with the prior art, the invention has the following advantages:
(1) The molecular general formula of the minimum asymmetric unit of the zinc-based triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Belongs to a tetragonal system, and the space point group is P4/n;
(2) The metal organic framework material is subjected to autonomous assembly by a solvothermal ligand and metal atoms, and has the advantages of high structural stability, strong controllability, simple preparation method and easy operation;
(3) Fluorescence analysis of the metal organic framework material shows that the metal organic framework material emits blue light, the excitation wavelength of the metal organic framework material is 300-320 nm, and the emission wavelength of the metal organic framework material is 320-350 nm; the test result shows that after different metal ions are added, fe 3+ Has obvious quenching effect on the fluorescence of the compound. So that the compound can act as Fe 3+ The fluorescent probe of (1). Fe 3+ Quenching constant K of sv Up to 8.4X 10 3 M -1 . The metal organic framework material (Zn-MOF) is taken as Fe 3+ The fluorescent probe of (2) and has excellent selectivityHigh sensitivity and high sensitivity.
Drawings
FIG. 1 is a diagram of coordination environment of example 1;
FIG. 2 is a stacking diagram of example 1;
FIG. 3 is a fluorescence spectrum of example 1;
FIG. 4 is the chromaticity diagram (CIE) (λ) of example 1 ex ＝304nm)；
FIG. 5 is Fe detection of example 1 3+ Fluorescence spectrum of quenching;
FIG. 6 shows different concentrations of Fe in example 1 3+ A spectrum of the effect on the fluorescence intensity of Zn-MOF;
FIG. 7 is a Powder XRD (PXRD) diffraction pattern of example 1;
FIG. 8 is a Thermogravimetric (TG) curve of example 1.
Detailed Description
The technical solutions of the present invention are described in detail below with reference to the embodiments, which are not meant to limit the present invention.
All reagents used were commercially available, zinc nitrate hexahydrate and 5-tert-butylisophthalic acid were from the national pharmaceutical group chemicals, inc., and acetonitrile and benzotriazole were from Shanghai Aladdin reagents, inc.
It should be noted that:
powder X-ray diffraction test conditions: tube voltage 40Kv, tube current 10Ma, cu-Ka radiation, wavelength of
The test angle range is 5-50 degrees, the step length is 0.02 degree, and the scanning speed is 6 degrees/min; TG/DTA test conditions: under the protection of nitrogen, the temperature rise interval is from room temperature to 800 ℃, and the temperature rise rate is 10 ℃ min -1 (ii) a Fluorescence analysis was performed using a spectrofluorometer FS5 fluorescence spectrometer.
Example 1 the minimum asymmetric unit of the zinc-based triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Synthesis of (2)
Accurately weighing 0.03mmol of zinc nitrate hexahydrate, 0.02mmol of benzotriazole and 0.01mmol of 5-tert-butyl isophthalic acid according to a proportion, adding into a glass tube, adding 2Ml of acetonitrile and 1Ml of water, ultrasonically dissolving until the solution becomes clear, sealing the glass tube, putting into a constant-temperature drying oven, reacting for 48 hours at 100 ℃, naturally cooling to room temperature, and filtering to obtain the zinc-based luminescent metal organic framework material (Zn-MOF).
Example 2 the minimum asymmetric unit of the zinc-based triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Synthesis of (2)
Accurately weighing 0.06mmol of zinc nitrate hexahydrate, 0.04mmol of benzotriazole and 0.02mmol of 5-tert-butylisophthalic acid according to a proportion, adding into a glass tube, adding 4M1 acetonitrile and 2M1 water, ultrasonically dissolving until the solution becomes clear, sealing the glass tube, putting into a constant-temperature drying oven, reacting at 100 ℃ for 72 hours, naturally cooling to room temperature, and filtering to obtain the same zinc-based luminescent metal organic framework material as in example 1.
Example 3 the minimum asymmetric unit of the zinc-based triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Synthesis of (2)
Accurately weighing 0.3mmol of zinc nitrate hexahydrate, 0.2mmol of benzotriazole and 0.1mmol of 5-tert-butyl isophthalic acid according to a proportion, adding into a glass bottle, adding 20M1 acetonitrile and 10M1 water, ultrasonically dissolving until the solution becomes clear, placing into a constant-temperature drying oven, reacting at 120 ℃ for 72 hours, naturally cooling to room temperature, and filtering to obtain the same zinc-based luminescent metal organic framework material as in example 1.
Example 4 crystal structure determination of the zinc-based triazole luminescent materials of examples 1, 2 and 3:
the zinc-based luminescent metal organic framework material-bulk transparent crystal prepared in examples 1 to 3, which had a suitable size, was selected under a microscope, and diffraction point data was collected using a Bruker SMART APEX CCD detector. Crystals of the metal organic framework material were glued to the tips of the glass filaments with an epoxy glue at a temperature of 293K and collected with Mo K α radiation (λ =0.071073 nm) radiation. The diffraction intensity data were corrected for Lp factor and empirical absorption. The crystal structure analysis and calculation are completed by using a SHELXL program, the full matrix least square method correction is carried out on all non-hydrogen atom coordinates and anisotropic thermal parameters, and hydrogen atoms are refined by a theoretical hydrogenation method and participate in the calculation of structural factors. The test results show that the implementation method of example 1 is better, the crystal data is more complete, and the related crystallography data are shown in table 1.
TABLE 1 minimum asymmetric Unit of Metal organic framework materials [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Crystallographic data of (2)
| Molecular formula | C 36 H 32 N 6 O 8 Zn 3 |
| Molecular weight | 872.78 |
| Crystal system | Tetragonal |
| Space group | P4/n |
| a/nm | 21.169(6) |
| b/nm | 21.169(6) |
| c/nm | 9.021(3) |
| α/(°) | 90 |
| β/(°) | 90 |
| γ/(°) | 90 |
| Volume V/nm 3 | 4043(3) |
| Z | 4 |
| Density of | 1.434 |
| Absorption factor | 1.820 |
| F(000) | 1776.0 |
| Final R indices[I＞2sigma(I)] | 0.0658，0.1629 |
| R indices(all data) | 0.0700，0.1657 |
Example 5 application of Zinc-based triazole luminescent Material
The fluorescence property of the zinc-based triazole luminescent material prepared in the example 1 is tested as follows:
FIG. 3 is a fluorescence property test spectrum of the zinc-based triazole luminescent material prepared in example 1, wherein the excitation wavelength is 304nm, and the maximum emission wavelength is 335nm; FIG. 4 is a chromaticity diagram (CIE) of zinc-based triazole luminescent materials prepared in example 1, wherein the CIE diagram coordinates are (0.212,0.224) (lambda) ex ＝304nm)。
To is directed atZinc-based triazole luminescent material prepared in example 1 for detecting Fe 3+ Detection of the fluorescent probe of (1):
FIG. 5 is a fluorescence spectrum of the zinc-based triazole luminescent material prepared in example 1 after different metal ions are added dropwise. Firstly, preparing 1mM suspension of the zinc-based triazole luminescent material aqueous solution of the embodiment 1, then respectively dripping different metal cation solutions to 10mM, ultrasonically mixing uniformly, exciting by 304nm and recording the change of fluorescence. The results show that Co 2+ ，Cd 2+ And Ni 2+ Has little effect on its fluorescence; k + And Mn 2+ The zinc-based triazole luminescent material has the function of reducing the fluorescence, but the zinc-based triazole luminescent material can be obviously seen in Fe 3+ The fluorescence intensity was completely quenched in the presence. This shows that the zinc-based luminescent metal organic framework material of example 1 is paired with Fe 3+ Has strong adsorption capacity, so that the compound has Fe adsorption capacity 3+ The ions have strong selective detection capability. FIG. 6 shows that Fe with different concentrations is dripped into the zinc-based triazole luminescent material prepared in example 1 3+ Fluorescence spectrum after the solution was analyzed by gradually adding Fe (5. Mu.L in one drop) at a concentration of 2mM 3+ The solution was added to a suspension (2 mM) of the zinc-based triazole luminescent material of example 1, mixed well and the change in fluorescence intensity was recorded. With analyte Fe 3+ The solution is gradually dripped, and the fluorescence intensity of the zinc-based triazole luminescent material prepared in the embodiment 1 is sharply reduced. The quenching efficiency was evaluated by using the Stern-Volmer (SV) equation: i is 0 /I＝K SV [Q]+1 wherein I 0 And I is the fluorescence intensity before and after dropping the analyte, [ Q ] respectively]Ksv is a quenching constant for quantitative evaluation of sensing efficiency as the concentration of the analyte, and a larger value indicates a higher quenching efficiency. By calculating Fe 3+ Quenching constant K of sv Up to 8.4X 10 3 M -1 And K of typical organic compounds sv Is 10 4 M -1 For example, [ Cd (PAM) (4-bpdb) 1.5 reported by RuiLv et al in 2018]·DMF(3500M -1 PAM =4,4-methylenebis (3-hydroxy-2-naphthalene-carboxy) acid), 4-bpdb =1,4-bis (4-pyridyl) -2,3-diaza-1,3-butadiene)) detected Fe 3+ Quenching constant K of sv Is 3500M -1 . Indicating a high degree of selectivity for the Zn-MOF prepared in example 1. So that the Zn-MOF acts as Fe 3+ The fluorescent probe has excellent selectivity.
Powder XRD (PXRD) diffraction test for the zinc-based triazole luminescent material prepared in example 1 above:
FIG. 7 is a PXRD diffraction test of a Degassed sample (Degassed) of the zinc-based triazole luminescent material prepared in example 1 of the present invention under a vacuum condition at 100 ℃ and a comparison graph of the PXRD of the non-Degassed sample (As-made) of example 1 and the PXRD simulated by using crystal data, wherein it can be seen that the simulated diffraction peak of the material prepared in example 1 corresponds to the diffraction peak measured in the actual experiment.
Thermogravimetric (TG) analysis test of the zinc-based triazole luminescent material prepared in the above example 1:
FIG. 8 is a thermal stability test of the zinc-based triazole luminescent material of example 1, and it can be seen from the figure that the metal organic framework material can be stabilized to 510 ℃, and the structure begins to collapse and decompose after 510 ℃, thus having better thermal stability.
Since fluorescence detection provides a selective detection of Fe 3+ The method of (1). These metal ions are widely present in water, and fluorescence detection is not affected by other metal ions in water.
Fluorescence property of the metal organic framework material prepared in embodiment 2 or 3 of the invention, fe in aqueous solution 3+ The ion detection and Thermogravimetric (TG) analysis tests were similar to those of the metal-organic framework material prepared in example 1.
Claims (10)
1. The zinc-based triazole luminescent material is characterized in that the chemical formula of the minimum asymmetric unit of the zinc-based triazole luminescent material is [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]Wherein BTA represents benzotriazole, 5-tbuip represents 5-tert-butylisophthalic acid, [ Zn ] 3 (BTA) 2 (5-tbuip) 2 ]The structural formula of (A) is as follows:
2. The zinc-based triazole luminescent material of claim 1, wherein the excitation wavelength of the zinc-based triazole luminescent material is 300-320 nm, and the emission wavelength is 320-350 nm.
3. The preparation method of the zinc-based triazole luminescent material of claim 1 or 2, which is characterized by comprising the following steps: weighing zinc nitrate hexahydrate, benzotriazole and 5-tert-butyl isophthalic acid, adding into a reaction container, adding a proper amount of acetonitrile and water, ultrasonically dissolving until the solution becomes clear, putting into a constant-temperature drying oven, reacting at 100-120 ℃ for 2-3 days, naturally cooling to room temperature, and filtering to obtain colorless rod-like crystals, namely the zinc-based triazole luminescent material.
4. The preparation method of zinc-based triazole luminescent material of claim 3, wherein the molar ratio of the zinc nitrate hexahydrate, the benzotriazole and the 5-tert-butyl isophthalic acid is 3: 2: 1.
5. The preparation method of the zinc-based triazole luminescent material as claimed in claim 3, wherein the volume ratio of the acetonitrile to the water is 2: 1.
6. The application of the zinc-based triazole luminescent material of claim 1 or 2 in the preparation of light emitting diodes or biological imaging or fluorescence detection.
7. A fluorescent probe, characterized in that the fluorescent probe is made of the zinc-based triazole luminescent material of claim 1 or 2.
8. The fluorescent probe of claim 7, wherein the fluorescent probe is for detecting Fe 3+ The fluorescent probe of (1).
9. The fluorescent probe of claim 8, wherein the Fe 3+ Quenching constant K of sv Up to 8.4X 10 3 M -1 。
10. Fe 3+ The detection method is characterized in that the detection method adopts the zinc-based triazole luminescent material of claim 1 or 2 or the fluorescent probe of claim 7 to contain Fe 3+ The solution of ions is detected.
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