CN111944163B - 5-carbazolyl isophthalic acid cadmium complex and preparation method and application thereof - Google Patents
5-carbazolyl isophthalic acid cadmium complex and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a 5-carbazolyl cadmium isophthalate complex as well as a preparation method and application thereof, and belongs to the technical field of long-afterglow materials. The chemical formula of the complex provided by the invention is Cd3(H2O)3(DMA)2(CZIP)3Wherein DMA is N, N-dimethylacetamide, and CZIP has a structure shown in formula I; the complex belongs to a monoclinic system, and the space group is P21C, unit cell parameter of
α＝90°，β＝91.588(2)°，γ＝90°，
The 5-carbazolyl cadmium isophthalate complex provided by the invention is expected to be applied to the field of luminescent materials, and especially can be applied as a long afterglow material.
Description
Technical Field
The invention relates to the technical field of long afterglow materials, in particular to a 5-carbazolyl isophthalic acid cadmium complex and a preparation method and application thereof.
Background
At present, researches on various metal-organic coordination compound materials formed by coordination self-assembly or controllable self-assembly of organic ligands and metal ions are active, because coordination compounds not only have interesting and various molecular structures and topological structures, but also show attractive application prospects in the fields of new materials such as fluorescence, adsorption, catalysis and magnetism. Since cadmium metal complexes have luminescence characteristics, a large number of synthesis and research have been conducted, and thus, cadmium metal complexes have become one of the hot research points in coordination chemistry. Isophthalic acid and derivatives thereof are important organic ligands, and some molecular-based coordination compound materials constructed by the reaction of the ligands and metal ions are widely synthesized and reported and show excellent potential performance.
Solar energy is a clean energy with nearly endless reserves, however, besides the low utilization rate of solar energy, the use of solar energy is limited by the place and time, and the solar energy device is difficult to continuously work in dark environment. Therefore, the search for materials that can efficiently utilize solar energy and still work continuously in dark environment is a key issue to be solved. The long afterglow material is a material capable of storing and slowly releasing light energy after illumination, is an important energy-saving environment-friendly material, develops different types of long afterglow materials, and has important significance for solving the problem and meeting diversified requirements.
Disclosure of Invention
The invention aims to provide a 5-carbazolyl isophthalic acid cadmium complex, a preparation method and application thereof, and the 5-carbazolyl isophthalic acid cadmium complex is expected to be applied to the field of luminescent materials through fluorescence and phosphorescence performance tests, and particularly can be applied as a long afterglow material.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a 5-carbazolyl isophthalic acid cadmium complex with a chemical formula of Cd3(H2O)3(DMA)2(CZIP)3Wherein DMA is N, N-dimethylacetamide, and CZIP has a structure shown in formula I:
the 5-carbazolyl isophthalic acid cadmium complex belongs to a monoclinic system, and the space group is P21C, unit cell parameter of
α＝90°，β＝91.588(2)°，γ＝90°，
Preferably, the 5-carbazolyl cadmium isophthalate complex has a three-dimensional supramolecular network structure.
The invention provides a preparation method of the 5-carbazolyl cadmium isophthalate complex, which comprises the following steps:
mixing 5-carbazolyl isophthalic acid, metal cadmium salt, water and N, N-dimethylacetamide, carrying out solvothermal reaction, and cooling to obtain the 5-carbazolyl isophthalic acid cadmium complex.
Preferably, the metal cadmium salt includes at least one of cadmium nitrate, cadmium chloride, cadmium acetate, and cadmium perchlorate.
Preferably, the volume ratio of the water to the N, N-dimethylacetamide is 1: (0.25-4), the ratio of the total volume of the water and the N, N-dimethylacetamide to the amount of the 5-carbazoly isophthalic acid and the metal cadmium salt is (5-6) mL: (0.05-0.20) mmol: (0.05 to 0.20) mmol.
Preferably, the temperature of the solvothermal reaction is 60-140 ℃, and the heat preservation time is 72-80 h; the heating rate of heating to the temperature required by the solvothermal reaction is 10-20 ℃/h.
Preferably, the temperature is reduced to 15-35 ℃ under natural conditions.
Preferably, after the temperature reduction, the method further comprises: carrying out solid-liquid separation on the system obtained after cooling, and sequentially washing and drying the obtained solid material to obtain the 5-carbazolyl isophthalic acid cadmium complex; wherein, the reagent that the washing adopted is water, dry for drying under the natural condition.
The invention provides an application of the 5-carbazolyl isophthalic acid cadmium complex serving as an optical material.
Preferably, the optical material is a long persistence luminescent material.
The present invention providesA 5-carbazolyl isophthalic acid cadmium complex with a chemical formula of Cd3(H2O)3(DMA)2(CZIP)3Wherein DMA is N, N-dimethylacetamide, and CZIP has a structure shown in formula I; the 5-carbazolyl isophthalic acid cadmium complex belongs to a monoclinic system, and the space group is P21C, unit cell parameter of
α＝90°，β＝91.588(2)°，γ＝90°，
The 5-carbazolyl isophthalic acid cadmium complex provided by the invention is subjected to fluorescence performance test, and the result shows that the complex is excited at 360nm and an emission peak is obtained at 436 nm; the phosphorescence performance test shows that the complex is excited at 360nm to obtain a wide emission peak between 400 nm and 700nm, and the complex displays orange yellow luminescence after an ultraviolet lamp is turned off, wherein the service life of the complex reaches 0.5 second. The method provides a theoretical basis for further developing the 5-carbazolyl isophthalic acid cadmium complex into an optical material, particularly a long-afterglow material. Meanwhile, the 5-carbazolyl cadmium isophthalate complex provided by the invention is characterized by thermogravimetric analysis, and the result shows that the skeleton can still stably exist at about 150 ℃, so that the complex has certain thermal stability, and the guarantee is provided for further development and application of the complex as a luminescent material.
The invention provides a preparation method of the 5-carbazolyl cadmium isophthalate complex, which comprises the following steps: mixing 5-carbazolyl isophthalic acid, metal cadmium salt, water and N, N-dimethylacetamide, carrying out solvothermal reaction, and cooling to obtain the 5-carbazolyl isophthalic acid cadmium complex. The method provided by the invention has the advantages of simple operation, good reproducibility and high product yield.
Drawings
FIG. 1 is a diagram of coordination environments of Cd1 and Cd2 in the complex prepared in example 1;
FIG. 2 is a diagram of coordination environment of Cd3 in the complex prepared in example 1;
FIG. 3 is a one-dimensional chain diagram of the complex prepared in example 1;
FIG. 4 is a three-dimensional network of the complex prepared in example 1;
FIG. 5 is a powder diffraction pattern of the complex prepared in example 1;
FIG. 6 is a thermogravimetric plot of the complex prepared in example 1;
FIG. 7 is a fluorescence spectrum of the complex prepared in example 1;
FIG. 8 is a phosphorescence map of the complex prepared in example 1;
FIG. 9 is a graph of the lifetime of the complex prepared in example 1;
FIG. 10 is a spectrum of the phosphorescence region of the complex prepared in example 1.
Detailed Description
The invention provides a 5-carbazolyl isophthalic acid cadmium complex with a chemical formula of Cd3(H2O)3(DMA)2(CZIP)3Wherein DMA is N, N-dimethylacetamide, and CZIP (5-carbazolyl isophthalate ion) has a structure shown in formula I:
the 5-carbazolyl isophthalic acid cadmium complex belongs to a monoclinic system, and the space group is P21C, unit cell parameter of
α＝90°，β＝91.588(2)°，γ＝90°，
In the present invention, 5-carbazolylaliphthalic acid (H)2CZIP) has the structure shown in formula II:
in the present invention, the 5-carbazolylmenzenediThe cadmium formate complex has a three-dimensional supermolecular network structure. Specifically, the basic structural unit of the 5-carbazolyl cadmium isophthalate complex contains three CdIIIon, three CdIIThe ions are all hexacoordinated structures, six coordinating atoms of Cd1 are five oxygen atoms from four 5-carbazolyl isophthalate ions and one oxygen atom of DMA, six coordinating atoms of Cd2 are four oxygen atoms from three 5-carbazolyl isophthalate ions and two oxygen atoms of two water molecules, and six coordinating atoms of Cd3 are four oxygen atoms from three 5-carbazolyl isophthalate ions and one oxygen atom of DMA and one oxygen atom of one water molecule. Cd [ Cd ]IIThe ions are linked to form a one-dimensional chain through 5-carbazolyl m-phthalic acid radical ions. Having a pi … pi interaction between the carbazolyl groups of the 5-carbazolyisophthalic acid radical ion, the ring center spacing being
This action links one-dimensional chains into three-dimensional supramolecular structures.
The invention provides a preparation method of the 5-carbazolyl cadmium isophthalate complex, which comprises the following steps:
mixing 5-carbazolyl isophthalic acid, metal cadmium salt, water and N, N-dimethylacetamide, carrying out solvothermal reaction, and cooling to obtain the 5-carbazolyl isophthalic acid cadmium complex.
In the present invention, the source of the 5-carbazolyisophthalic acid is not particularly limited, and commercially available products known to those skilled in the art may be used. In the present invention, the metal cadmium salt preferably includes at least one of cadmium nitrate, cadmium chloride, cadmium acetate, and cadmium perchlorate, more preferably cadmium nitrate, cadmium chloride, cadmium acetate, or cadmium perchlorate, and in an embodiment of the present invention, cadmium nitrate tetrahydrate, cadmium chloride, cadmium acetate dihydrate, or cadmium perchlorate hexahydrate is particularly used. In the present invention, the water and N, N-dimethylacetamide are solvents for the solvothermal reaction, and the volume ratio of the water to the N, N-dimethylacetamide is preferably 1: (0.25-4), specifically 1:0.25, 1:1, 1:2 or 1: 4. In the present invention, the ratio of the total volume of the water and N, N-dimethylacetamide to the amount of the 5-carbazoly isophthalic acid and the metal cadmium salt is preferably (5 to 6) mL: (0.05-0.20) mmol: (0.05-0.20) mmol, which may be specifically 6 mL: 0.1 mmol: 0.1mmol, 6 mL: 0.12 mmol: 0.12mmol, 5 mL: 0.06 mmol: 0.18mmol or 5 mL: 0.18 mmol: 0.06 mmol.
In the invention, the temperature of the solvothermal reaction is preferably 60-140 ℃, and specifically can be 60 ℃, 80 ℃, 100 ℃ or 120 ℃; the heat preservation time of the solvothermal reaction is preferably 72-80 h, and more preferably 72-75 h; the heating rate of heating to the temperature required by the solvothermal reaction is preferably 10-20 ℃/h, and more preferably 10-15 ℃/h. In the invention, the solvothermal reaction is preferably carried out in a reaction kettle, and specifically, the 5-carbazolyl isophthalic acid, the metal cadmium salt, water and N, N-dimethylacetamide are sealed in the reaction kettle, heated to 60-140 ℃ at the speed of 10-20 ℃/h, and subjected to the solvothermal reaction by keeping the temperature for 72-80 h.
In the invention, after the solvothermal reaction is finished, the obtained system is cooled to obtain a system containing colorless blocky crystals, and the crystals are the 5-carbazolyl isophthalic acid cadmium complex. In the invention, the temperature is preferably reduced to 15-35 ℃ under natural conditions, and in the embodiment of the invention, the temperature is specifically reduced to room temperature (25 ℃) under natural conditions.
In the present invention, after the temperature reduction, it is preferable that the method further comprises: and (3) carrying out solid-liquid separation on the system obtained after cooling, and sequentially washing and drying the obtained solid material to obtain the 5-carbazolyl isophthalic acid cadmium complex. The solid-liquid separation method is not particularly limited, and a method known to those skilled in the art, such as filtration, may be used. In the invention, the reagent used for washing is preferably water, and the drying is preferably air drying under natural conditions.
The invention provides an application of the 5-carbazolyl isophthalic acid cadmium complex as an optical material; in the present invention, the optical material is preferably a long persistence luminescent material. The 5-carbazolyl isophthalic acid cadmium complex provided by the invention emits blue fluorescence under the excitation of ultraviolet light, and an ultraviolet lamp is turned off to emit orange yellow light visible to naked eyes.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Dissolving 5-carbazolyl isophthalic acid (33.1mg,0.1mmol) and cadmium nitrate tetrahydrate (30.8mg,0.1mmol) in water (3mL) and N, N-dimethylacetamide (DMA,3mL), sealing in a reaction kettle, heating to 80 ℃ at the speed of 10 ℃/h, maintaining the temperature for 3 days, naturally cooling to room temperature (25 ℃) to obtain a system containing colorless blocky crystals, filtering to separate the crystals, and sequentially carrying out water washing and natural drying treatment to obtain a target product with the yield of about 60%.
The obtained 5-carbazolyl isophthalic acid cadmium complex is further characterized as follows:
(1) crystal structure determination of the Complex
Selecting a synthesized transparent crystal with good appearance and proper size, adhering the crystal on a capillary glass rod, placing the capillary glass rod on a Supernova, Single source at offset, Eos 2X-ray Single crystal diffractometer at room temperature for testing, and filtering Mo-Ka rays by a graphite monochromator
As an incident light source, to
The scanning mode, collecting diffraction intensity data over a range of angles, using Olex 2, using Intrinsic pharmacy in the ShelXT package to analyze the structure, using the least squares method in the ShelXL package to refine the structure. Detailed crystal determination data are shown in table 1; the key length and key angle data of interest are shown in table 2; the crystal structure is shown in the figures 1-4, wherein figure 1 is a coordination environment diagram of Cd1 and Cd2 in the complex, and figure 2 is a coordination environment diagram of Cd1 and Cd2 in the complexThe coordination environment diagram of Cd3, the figure 3 is a one-dimensional chain diagram of the complex, and the figure 4 is a three-dimensional network diagram of the complex. As can be seen from tables 1-2 and FIGS. 1-4, the complex of the present invention belongs to the monoclinic system, and has a space group of P21C, unit cell parameter of
α＝90°，β＝91.588(2)°，γ＝90°，
The basic structure of the complex is a three-dimensional supramolecular network structure, and the basic structural unit contains three CdIIIon, three CdIIThe ions are all hexacoordinated structures, six coordinating atoms of Cd1 are five oxygen atoms from four 5-carbazolyl isophthalate ions and one oxygen atom of DMA, six coordinating atoms of Cd2 are four oxygen atoms from three 5-carbazolyl isophthalate ions and two oxygen atoms of two water molecules, and six coordinating atoms of Cd3 are four oxygen atoms from three 5-carbazolyl isophthalate ions and one oxygen atom of DMA and one oxygen atom of one water molecule. Cd [ Cd ]IIThe ions are linked to form a one-dimensional chain through 5-carbazolyl m-phthalic acid radical ions. Having a pi … pi interaction between the carbazolyl groups of the 5-carbazolyisophthalic acid radical ion, the ring center spacing being
This action links one-dimensional chains into three-dimensional supramolecular structures.
TABLE 1 Primary crystallographic data for the complexes
TABLE 2 complexesImportant bond length
Angle of harmony key (°)
Symmetric codes A: x, -y, z-1/2; b-x +1/2, -y +1/2, -z.
(2) Powder X-ray diffraction phase purity characterization of the Complex
FIG. 5 is a powder diffraction pattern (instrument model: Bruker/D8 Advance) of the complex prepared in example 1. As can be seen from FIG. 5, the powder X-ray diffraction pattern of the complex is consistent with the experimentally simulated diffraction pattern, which shows that it has reliable phase purity and provides assurance for its application as an optical material.
(3) Characterization of thermal stability of the Complex
FIG. 6 is a thermogravimetric graph (instrument model: SII EXStar6000TG/DTA6300) of the complex prepared in example 1. As can be seen from FIG. 6, the complex has a skeleton which can stably exist at about 150 ℃ and has a certain thermal stability, so that the thermal stability guarantee is provided for further development and application of the complex as an optical material; with increasing temperature, the organic ligand is eventually totally lost and the final product should be a metal oxide.
(4) Study of solid fluorescence properties of complexes
The complex prepared in example 1 was subjected to a solid fluorescence test (instrument model: HITACHI/F-7000), and the results are shown in FIG. 7. As can be seen from FIG. 7, the complex is excited at 360nm and an emission peak is obtained at 436nm, i.e., the complex emits blue fluorescence.
(5) Solid phosphorescent Properties of the complexes
The solid phosphorescence test (instrument model: Edinburgh FLS1000 steady-state transient fluorescence spectrometer) is carried out on the complex prepared in the example 1, and the result is shown in fig. 8-10, wherein fig. 8 is a phosphorescence spectrum of the complex, fig. 9 is a lifetime graph of the complex, and fig. 10 is a phosphorescence color region spectrum of the complex. As can be seen from FIGS. 8-10, the complex is excited at 360nm to obtain a broad emission peak between 400 nm and 700nm, and after the ultraviolet lamp is turned off, the complex shows orange-yellow luminescence, and the service life of the complex reaches 0.5 second.
Example 2
Dissolving 5-carbazolyl isophthalic acid (19.9mg,0.06mmol) and cadmium chloride (79.2mg,0.18mmol) in water (4mL) and DMA (1mL), sealing in a reaction kettle, heating to 120 ℃ at the speed of 10 ℃/h, maintaining the temperature for 3 days, naturally cooling to room temperature to obtain a system containing colorless blocky crystals, filtering to separate the crystals, washing and naturally drying in sequence to obtain a target product, namely the 5-carbazolyl isophthalic acid cadmium complex, wherein the yield is about 55%.
Example 3
Dissolving 5-carbazolyl isophthalic acid (59.6mg,0.18mmol) and cadmium acetate dihydrate (16.0mg,0.06mmol) in water (1mL) and DMA (4mL), sealing in a reaction kettle, heating to 60 ℃ at the speed of 10 ℃/h, maintaining the temperature for 3 days, naturally cooling to room temperature to obtain a system containing colorless blocky crystals, filtering to separate the crystals, and washing and naturally drying sequentially to obtain a target product, namely the 5-carbazolyl isophthalic acid cadmium complex, wherein the yield is about 46%.
Example 4
Dissolving 5-carbazolyl isophthalic acid (39.7mg,0.12mmol) and cadmium perchlorate hexahydrate (50.4mg,0.12mmol) in water (2mL) and DMA (4mL), sealing in a reaction kettle, heating to 120 ℃ at the speed of 10 ℃/h, maintaining the temperature for 3 days, naturally cooling to room temperature to obtain a system containing colorless blocky crystals, filtering to separate the crystals, and washing and naturally drying the crystals in sequence to obtain a target product, namely the 5-carbazolyl isophthalic acid cadmium complex, wherein the yield is about 47%.
The 5-carbazolyl cadmium isophthalate complexes prepared in examples 2 to 4 were characterized by the method of example 1, and the results are consistent with those in example 1.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (9)
1. 5-carbazolyl isophthalic acid cadmium complex with chemical formula of Cd3(H2O)3(DMA)2(CZIP)3Wherein DMA is N, N-dimethylacetamide, and CZIP has a structure shown in formula I:
the 5-carbazolyl isophthalic acid cadmium complex belongs to a monoclinic system, and the space group isP21/cCell parameter ofa = 10.2368(2) Å，b = 15.6829(4) Å，c = 39.8412(8) Å，α= 90 °，β= 91.588(2) °，γ= 90 °，V = 6393.8(2) Å3。
2. The method for preparing the 5-carbazolyl cadmium isophthalate complex as defined in claim 1, comprising the steps of:
mixing 5-carbazolyl isophthalic acid, metal cadmium salt, water and N, N-dimethylacetamide, carrying out solvothermal reaction, and cooling to obtain the 5-carbazolyl isophthalic acid cadmium complex.
3. The method of claim 2, wherein the metal cadmium salt includes at least one of cadmium nitrate, cadmium chloride, cadmium acetate, and cadmium perchlorate.
4. The method according to claim 2 or 3, wherein the volume ratio of the water to the N, N-dimethylacetamide is 1: (0.25-4), the ratio of the total volume of the water and the N, N-dimethylacetamide to the amount of the 5-carbazoly isophthalic acid and the metal cadmium salt is (5-6) mL: (0.05-0.20) mmol: (0.05 to 0.20) mmol.
5. The preparation method according to claim 2, wherein the temperature of the solvothermal reaction is 60-140 ℃, and the holding time is 72-80 h; the heating rate of heating to the temperature required by the solvothermal reaction is 10-20 ℃/h.
6. The preparation method according to claim 2 or 5, wherein the temperature reduction is carried out to 15-35 ℃ under natural conditions.
7. The method of claim 2, further comprising, after cooling: carrying out solid-liquid separation on the system obtained after cooling, and sequentially washing and drying the obtained solid material to obtain the 5-carbazolyl isophthalic acid cadmium complex; wherein, the reagent that the washing adopted is water, dry for drying under the natural condition.
8. Use of the 5-carbazolyl-cadmium isophthalate complex as defined in claim 1 as an optical material.
9. Use according to claim 8, wherein the optical material is a long persistence luminescent material.
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| A stable 3D Cd(II) metal–organic framework for highly sensitive detection of Cu2+ ions and nitroaromatic explosives;Jian-Long Du ，等;《RSC Adv.》;20171231;第7卷;第49618–49625页 * |
| A supramolecular approach for designing emissive solid-state carbazole arrays;Liubov M. Lifshits，等;《Chem. Commun.》;20151231;第51卷;第11603-11606页 * |
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