CN117903454A - NEMOFs material containing bisoxazole ligand and preparation method thereof - Google Patents

NEMOFs material containing bisoxazole ligand and preparation method thereof Download PDF

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CN117903454A
CN117903454A CN202410110451.4A CN202410110451A CN117903454A CN 117903454 A CN117903454 A CN 117903454A CN 202410110451 A CN202410110451 A CN 202410110451A CN 117903454 A CN117903454 A CN 117903454A
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ligand
solution
nemofs
azole
rich
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彭盼盼
石俊涛
史淑婧
赵霞
汪慧思
屈炜宸
张天伟
郭翔
李洪旭
陶博文
顾健
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Hubei Institute of Aerospace Chemical Technology
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Hubei Institute of Aerospace Chemical Technology
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Abstract

The invention relates to the technical field of energetic material preparation, and in particular discloses a NEMOFs material containing a bisoxazole ligand and a preparation method thereof, and a NEMOFs material containing the bisoxazole ligand, which comprises the following steps: step one: the three solutions were separately prepared including: a metal ion salt solution, a polycyclic nitrogen-rich azole main ligand solution and a monocyclic nitrogen-rich azole auxiliary ligand solution; step two: mixing the three solutions in the first step in sequence, adding a first part of strong acid solution into the mixed solution, stirring, and filtering to obtain clear and transparent mixed mother solution; step three: and (3) adding a second part of strong acid solution into the clear and transparent mixed mother solution again, and separating out crystals after the high-temperature reaction is finished to obtain the NEMOFs material containing the bisoxazole ligand. Not only can provide more energy sources for EMOFs materials, but also can further regulate and control skeleton ring tension on the basis of changing coordination modes, thereby achieving the improvement of EMOFs materials in the aspects of structure, performance, application and the like, and having great significance.

Description

NEMOFs material containing bisoxazole ligand and preparation method thereof
Technical Field
The invention relates to the technical field of preparation of energetic materials, in particular to a NEMOFs material containing a bifluoride azole ligand and a preparation method thereof.
Background
The Energetic Metal Organic Framework (EMOFs) material is a kind of coordination compound which is formed by self-assembling molecules through the coordination interaction of polynitroazole energetic organic ligands and metal ions and has different dimensionalities and spatial structures, and the coordination compound is widely focused by virtue of stable geometric topological structure, designable energetic ligands, adjustable detonation performance and safety. Wherein, when EMOFs material has a neutral charge on the backbone and no backbone counter-ion exists in the crystal structure, the material is called neutral EMOFs (nemfs) material. Unlike conventional energetic materials, the energy of EMOFs is mainly derived from the chemical energy and the ring tension of the skeleton structure contained in the energetic organic ligand molecules, and the energy level of EMOFs can be effectively improved by adopting the energetic ligand with high energy density. From the chemical structure of EMOFs materials, the EMOFs materials reported are also predominantly single coordinated metal ions and single organic energetic ligands. Therefore, the preparation of novel EMOFs materials by changing different single coordinated metal ions or single organic energetic ligands is currently the most dominant method for regulating the physicochemical properties of the materials. However, for EMOFs materials, whether the coordinating metal ion or the organic energetic ligand is altered, the energy is essentially derived from only a single energetic ligand, and the energy control range is extremely limited.
Disclosure of Invention
Aiming at the problems, from the aspect of energy sources, the quantity of organic energetic ligands is taken as an entry point, two kinds of nitrogen-rich azole energetic ligands are introduced into the skeleton structure of EMOFs material, and a novel NEMOFs material containing double nitrogen-rich azole ligands is constructed, so that more energy sources can be provided for EMOFs material, skeleton ring tension can be further regulated and controlled on the basis of changing coordination modes, and further the promotion of EMOFs material in the aspects of structure, performance, application and the like is achieved, and the significance is great.
The invention aims to provide a preparation method of NEMOFs material containing a bisoxazole ligand.
The second object of the invention is to provide NEMOFs materials containing the bifonazole ligand.
The first technical scheme adopted by the invention is as follows: a preparation method of NEMOFs material containing bifonazole ligand comprises the following steps:
Step one: the three solutions were separately prepared including: a metal ion salt solution, a polycyclic nitrogen-rich azole main ligand solution and a monocyclic nitrogen-rich azole auxiliary ligand solution;
Step two: mixing the three solutions in the first step in sequence, adding a first part of strong acid solution into the mixed solution, stirring, and filtering to obtain clear and transparent mixed mother solution;
Step three: and (3) adding a second part of strong acid solution into the clear and transparent mixed mother solution again, and separating out crystals after the high-temperature reaction is finished to obtain the NEMOFs material containing the bisoxazole ligand.
Preferably, the metal ion salt in the metal ion salt solution in the first step is one or more of Cu(NO3)2、Cu(BF4)2、CuSO4、Co(NO3)2、Co(BF4)2、CoCl2、Zn(NO3)2、Fe(NO3)2 and Ni (NO 3)2 and hydrate corresponding to the metal ion salt).
Preferably, in the step one, the polycyclic nitrogen-rich azole main ligand in the polycyclic nitrogen-rich azole main ligand solution is 4,4 '-azo-1, 2, 4-triazole or/and 4,4' -bi-1, 2, 4-triazole.
Preferably, in the step one, the monocyclic nitrogen-rich azole auxiliary ligand in the monocyclic nitrogen-rich azole auxiliary ligand solution is one or more of 3, 4-dinitropyrazole, 3, 5-dinitropyrazole and 2, 4-dinitroimidazole.
Preferably, in the second step, the mixing sequence is that the polycyclic nitrogen-rich azole main ligand solution and the monocyclic nitrogen-rich azole auxiliary ligand solution are mixed first, and then the metal ion salt solution is added.
Preferably, the molar ratio of the metal ion salt, the polycyclic nitrogen-rich azole main ligand and the monocyclic nitrogen-rich azole auxiliary ligand of the three solutions in the second step is 4:1:1-1:1:4.
Preferably, in the second step, the first part of the strong acid solution accounts for 1% -10% of the total volume of the solvent;
In the third step, the second part of strong acid solution is 1-10 drops;
The mass concentration of the strong acid solution is one or more of 38% concentrated HCl, 98% concentrated H 2SO4 and 68% concentrated HNO 3.
Preferably, in the second step, the stirring temperature is 40-70 ℃ and the stirring time is 0.5-2 h.
Preferably, the high temperature reaction conditions in the third step are: 60-160 deg.c for 2-7 days.
The second technical scheme adopted by the invention is as follows: NEMOFs materials containing bifonazole ligands.
The beneficial effects of the technical scheme are that:
(1) The method provided by the invention uses two kinds of nitrogen-rich azole compounds as energy-containing ligands at the same time, and realizes the preparation of a novel NEMOFs material containing double nitrogen-rich azole ligands by means of the cooperative coordination interaction between molecules of the two kinds of ligands. The product obtained by the method has high purity and no byproducts.
(2) The NEMOFs material containing the double-nitrogen-rich ligand provided by the invention maintains a high-regularity framework structure, has excellent thermal stability and mechanical sensitivity, and can be used as a potential heat-resistant insensitive explosive.
(3) When different nitrogen-rich ligand systems are adopted in the method, NEMOFs materials with different framework structures can be prepared, and the comparison difference of the physicochemical properties is obvious.
Drawings
FIG. 1 is a diagram showing chemical structural formulas of the polycyclic azole-rich main ligand (ATRZ, BTRZ) and the monocyclic azole-rich auxiliary ligand (3, 4-DNP, 3,5-DNP and 2, 4-DNI).
FIG. 2 is an optical microscope photograph of NEMOF-1 materials described in example 1.
FIG. 3 is a graph of the coordination environment of NEMOF-1 material described in example 1 as measured by X-ray single crystal diffraction (SXRD).
FIG. 4 is a Differential Scanning Calorimeter (DSC) spectrum of NEMOF-1 material described in example 1;
FIG. 5 is an optical microscope photograph of NEMOF-2 materials described in example 2;
FIG. 6 is a graph of the coordination environment of NEMOF-2 material described in example 2 as measured by SXRD;
FIG. 7 is a DSC profile of the NEMOF-2 material described in example 2;
FIG. 8 is an optical microscope photograph of NEMOF-3 materials described in example 3;
FIG. 9 is a graph of the coordination environment of NEMOF-3 material described in example 3 as measured by SXRD;
FIG. 10 is a DSC profile of the NEMOF-3 material described in example 3;
FIG. 11 is an optical microscope photograph of NEMOF-4 material described in example 4;
FIG. 12 is a graph of the coordination environment of NEMOF-4 material described in example 4 as measured by SXRD;
FIG. 13 is a DSC plot of NEMOF-4 material described in example 4.
Detailed Description
The following detailed description of embodiments of the application provides further details of the embodiments described, and it should be apparent that the embodiments described are merely some, rather than all, examples of the application. It should be noted that, without conflict, the embodiments of the present application and features of the embodiments may be combined with each other.
The terms first, second, and the like in the description and in the claims, if any, are used for distinguishing between similar elements and not necessarily for describing a particular sequential or chronological order. It is to be understood that the data so used may be interchanged where appropriate such that the embodiments described herein may be implemented in other sequences than those illustrated or otherwise described herein. Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements that are expressly listed or inherent to such process, method, article, or apparatus.
It should be understood that the term "and/or" as used herein is merely one relationship describing the association of the associated objects, meaning that there may be three relationships, e.g., a and/or B, may represent: a exists alone, A and B exist together, and B exists alone. In addition, the character "/" herein generally indicates that the front and rear associated objects are an "or" relationship.
Medicine, instrumentation and equipment:
(1) Unless otherwise specified, the materials and equipment employed are commercially available or are conventional in the art.
(2) The chemical structure of ATRZ used was as shown in FIG. 1 according to ATRZ described in document "Li S H,Pasng S P,Li X T,et al.Synthesis of new tetrazene(N-N＝N-N)-linked bi(1,2,4-triazole)[J].Chinese Chemical Letters,2005,18(10):1176-1178.".
(3) The synthesis of BTRZ used is according to the synthesis, characterization and crystal structure [ J ]. Energetic materials of the literature "Li Lei, chi, zhang Yong, et al, 4' -bi-1, 2, 4-triazole, 2013,21 (4): 429-433", the chemical formula of BTRZ is shown in FIG. 1.
(4) Synthesis of 3,4-DNP used is described in the literature "Wang Yinglei, ji Yueping, chen, et al, 3, 4-dinitropyrazole synthesis and Property Industry materials, 2011,19 (4): 377-379", the chemical formula of said 3,4-DNP is shown in FIG. 1.
(5) Synthesis of 3,5-DNP used was carried out in accordance with the literature "Wang Yinglei, zhang Zhizhong, wang Bazhou, et al, 3, 5-dinitropyrazole Synthesis Studies [ J ]. Energetic materials, 2007,15 (6): 574-576", the chemical formula of said 3,5-DNP being shown in FIG. 1.
(6) Synthesis of 2,4-DNI used was carried out according to the literature "Feng Lulu, cao Duanlin, wang Jianlong, et al, the progress of the synthesis of nitroimidazoles energetic compounds [ J ]. Energetic materials, 2015,23 (4): 376-385", the chemical formula of said 2,4-DNI being shown in FIG. 1.
(7) Optical microscope: an OLYMPUS-BX43 microscope manufactured by Orthobas corporation of Japan was used.
(8) SXRD test: a Rigaku RAXIS IP type diffractometer manufactured by Bruker corporation was used.
(9) DSC test: a differential scanning calorimeter of the type DSC-209 produced by Netzsch was used.
(10) True density testing: a AccupycII model 1345 full-automatic true density analyzer manufactured by Micromeritics corporation was used.
(11) Burst heat test: a Parr 6772 full-automatic oxygen bomb calorimeter manufactured by Parr company was used.
(12) Impact sensitivity test: BFH-10 type impact sensor manufactured by IDEA SCIENCE company was used.
(13) Friction sensitivity test: a FSKM-10 BAM friction sensor manufactured by IDEA SCIENCE was used.
Example 1
NEMOFs material containing double-nitrogen-rich ligand and preparation method thereof, the method comprises the following steps:
(1) Cu (NO 3)2·3H2 O (242 mg,1 mmol), ATRZ (82 mg,0.5 mmol) and 3,4-DNP (158 mg,1 mmol) were added to 5mL deionized water, heated, stirred for dissolution, and filtered to give a clear and transparent solution;
(2) Firstly placing ATRZ solution and 3,4-DNP solution in a three-mouth bottle, mixing and stirring for 10min, slowly dripping Cu (NO 3)2 solution, then continuously dripping 0.5mL 68% concentrated HNO 3 solution, heating to 60 ℃, preserving heat and stirring for reacting for 1h, and filtering to obtain clear and transparent mixed mother liquor;
(3) Transferring the obtained mother solution into a liner of a hydrothermal synthesis reaction kettle, adding 3 drops of 68% concentrated HNO 3 solution into the liner again, screwing up a metal shell of the reaction kettle, placing the whole reaction kettle in a 90 ℃ oven for standing for 4 days, taking out the reaction kettle, standing for 1 day at room temperature, and opening the kettle, wherein blue crystals shown in figure 2 are precipitated in the kettle, namely the NEMOF-1 material containing the bis-nitrogen-rich azole ligand.
As shown in FIG. 3, the coordination environment diagram of the NEMOF-1 material shows that NEMOF-1 is an energetic metal-organic framework material with Cu 2+ as a coordination center ion, ATRZ as a main bridging ligand and 3,4-DNP as an auxiliary balance ligand, and the molecular structural formula is abbreviated as [ Cu (ATRZ) (3, 4-DNP) 2(H2O)]n·[2(H2O)]n.
DSC measurements were performed on NEMOF-1 materials, as shown in FIG. 4, with a thermal decomposition temperature of 249.54 ℃. Further, other characterization tests are carried out on NEMOF-1 materials, and the result shows that the density is 1.761g cm -3, the heat explosion is 4790 kJ.kg -1, the impact sensitivity is 22J, the friction sensitivity is more than 360N, and the heat-resistant insensitive explosive with excellent comprehensive performance is provided.
Example 2
(1) Cu (NO 3)2·3H2 O (242 mg,1 mmol), ATRZ (82 mg,0.5 mmol) and 3,5-DNP (158 mg,1 mmol) were added to 5mL deionized water, heated, stirred for dissolution, and filtered to give a clear and transparent solution;
(2) Firstly placing ATRZ solution and 3,4-DNP solution in a three-mouth bottle, mixing and stirring for 10min, slowly dripping Cu (NO 3)2 solution, then continuously dripping 0.5mL 68% concentrated HNO 3 solution, heating to 60 ℃, preserving heat and stirring for reacting for 1h, and filtering to obtain clear and transparent mixed mother liquor;
(3) Transferring the obtained mother solution into a liner of a hydrothermal synthesis reaction kettle, adding 3 drops of 68% concentrated HNO 3 solution into the liner again, screwing up a metal shell of the reaction kettle, placing the whole reaction kettle in an oven at 80 ℃ for standing for 3 days, taking out the reaction kettle, standing for 1 day at room temperature, and opening the kettle, wherein light blue crystals as shown in figure 5 are precipitated in the kettle, namely the NEMOF-2 material containing the bis-nitrogen-rich azole ligand.
As shown in FIG. 6, the coordination environment diagram of the NEMOF-2 material shows that the NEMOF-2 material is an energetic metal-organic framework material taking Cu 2+ as a coordination center ion, ATRZ as a main bridging ligand and 3,5-DNP as an auxiliary balance ligand, and the molecular structural formula is abbreviated as [ Cu (ATRZ) (3, 5-DNP) 2]n.
DSC measurements were performed on NEMOF-2 materials, as shown in FIG. 7, with a thermal decomposition temperature of 317.26 ℃. Further, other characterization tests are carried out on NEMOF-2 materials, and the result shows that the heat-resistant insensitive explosive has the density of 1.873 g.cm -3, the heat explosion of 3883.2 kJ.kg -1, the impact sensitivity of 15J and the friction sensitivity of 252N, and is relatively excellent in comprehensive performance.
Example 3
(1) Cu (NO 3)2·3H2 O (242 mg,1 mmol), ATRZ (82 mg,0.5 mmol) and 2,4-DNI (158 mg,1 mmol) were added to 5mL deionized water, heated, stirred for dissolution, and filtered to give a clear and transparent solution;
(2) Firstly placing ATRZ solution and 2,4-DNI solution in a three-mouth bottle, mixing and stirring for 10min, slowly dripping Cu (NO 3)2 solution, then continuously dripping 0.5mL 68% concentrated HNO 3 solution, heating to 60 ℃, preserving heat and stirring for reacting for 1h, and filtering to obtain clear and transparent mixed mother liquor;
(3) Transferring the obtained mother solution into a liner of a hydrothermal synthesis reaction kettle, adding 3 drops of 68% concentrated HNO 3 solution into the liner again, screwing up a metal shell of the reaction kettle, placing the whole reaction kettle in a baking oven at 120 ℃ for standing for 5 days, taking out the reaction kettle, standing for 1 day at room temperature, and opening the kettle, wherein deep blue crystals shown in figure 8 are precipitated in the kettle, namely the NEMOF-3 material containing the bis-nitrogen-rich azole ligand.
As shown in FIG. 9, the coordination environment diagram of the NEMOF-3 material shows that NEMOF-3 is an energetic metal-organic framework material with Cu 2+ as a coordination center ion, ATRZ as a main bridging ligand and 2,4-DNI as an auxiliary balance ligand, and the molecular structural formula is abbreviated as [ Cu (ATRZ) (2, 4-DNI) 2]n.
DSC measurements were performed on NEMOF-3 materials, as shown in FIG. 10, with a thermal decomposition temperature of 319.59 ℃. Further, other characterization tests are carried out on NEMOF-3 materials, and the result shows that the density is 1.881g cm -3, the detonation heat is 3807.1 kJ.kg -1, the impact sensitivity is 16J, the friction sensitivity is 288N, and the heat-resistant insensitive explosive with relatively excellent comprehensive performance is provided.
Example 4
(1) Cu (NO 3)2·3H2 O (242 mg,1 mmol), BTRZ (68 mg,0.5 mmol) and 3,5-DNP (158 mg,1 mmol) were added to 5mL deionized water, heated, stirred for dissolution, and filtered to give a clear and transparent solution;
(2) Firstly placing BTRZ solution and 3,5-DNP solution in a three-mouth bottle, mixing and stirring for 10min, slowly dripping Cu (NO 3)2 solution, then continuously dripping 0.5mL 68% concentrated HNO 3 solution, heating to 60 ℃, preserving heat and stirring for reacting for 1h, and filtering to obtain clear and transparent mixed mother liquor;
(3) Transferring the obtained mother solution into a liner of a hydrothermal synthesis reaction kettle, adding 3 drops of 68% concentrated HNO 3 solution into the liner again, screwing up a metal shell of the reaction kettle, placing the whole reaction kettle in a baking oven at 100 ℃ for standing for 4 days, taking out the reaction kettle, standing for 1 day at room temperature, and opening the kettle, wherein blue crystals as shown in figure 11 are precipitated in the kettle, namely the NEMOF-4 material containing the bis-nitrogen-rich azole ligand.
As shown in FIG. 12, the coordination environment diagram of the NEMOF-4 material shows that NEMOF-4 is an energetic metal-organic framework material taking Cu 2+ as a coordination center ion, ATRZ as a main bridging ligand and 3,5-DNP as an auxiliary balance ligand, and the molecular structural formula is abbreviated as [ Cu (BTRZ) (3, 5-DNP) 2]n.
DSC measurements were performed on NEMOF-4 material, as shown in FIG. 13, with a thermal decomposition temperature of 306.42 ℃. Further, other characterization tests are carried out on NEMOF-3 materials, and the result shows that the density is 1.881g cm -3, the detonation heat is 3718.5 kJ.kg -1, the impact sensitivity is 22J, the friction sensitivity is 353N, and the heat-resistant insensitive explosive with relatively excellent comprehensive performance is provided. NEMOFs material performance test containing bifluoride azole ligand:
Table 1 single crystal unit cell parameters for the four NEMOFs materials described in examples 1-4.
As can be seen from Table 1, the invention introduces two kinds of energy-containing ligands of the nitrogen-rich azoles into the skeleton structure of EMOFs material, and successfully prepares a plurality of novel NEMOFs materials containing the ligands of the nitrogen-rich azoles, and NEMOFs materials containing the ligands of the nitrogen-rich azoles obtained by the method have excellent heat explosion, heat stability and mechanical sensitivity, and can be used as potential heat-resistant insensitive explosive candidates. In addition, the related report of NEMOFs materials containing the bisoxazole ligand does not appear at present, and the preparation of the compound provides a brand new research thought for the modification of metal organic framework energetic materials, and has wide application prospect and great significance.
It should be understood that the foregoing examples of the present invention are merely illustrative of the present invention and not limiting of the embodiments of the present invention, and that various other changes and modifications can be made by those skilled in the art based on the above description, and it is not intended to be exhaustive of all of the embodiments, and all obvious changes and modifications that come within the scope of the invention are defined by the following claims.

Claims (10)

1. A preparation method of NEMOFs material containing bifonazole ligand is characterized by comprising the following steps:
Step one: the three solutions were separately prepared including: a metal ion salt solution, a polycyclic nitrogen-rich azole main ligand solution and a monocyclic nitrogen-rich azole auxiliary ligand solution;
Step two: mixing the three solutions in the first step in sequence, adding a first part of strong acid solution into the mixed solution, stirring, and filtering to obtain clear and transparent mixed mother solution;
Step three: and (3) adding a second part of strong acid solution into the clear and transparent mixed mother solution again, and separating out crystals after the high-temperature reaction is finished to obtain the NEMOFs material containing the bisoxazole ligand.
2. The method for preparing NEMOFs materials containing bis-azole ligands according to claim 1, wherein in the first step, the metal ion salt in the metal ion salt solution is one or more of Cu(NO3)2、Cu(BF4)2、CuSO4、Co(NO3)2、Co(BF4)2、CoCl2、Zn(NO3)2、Fe(NO3)2 and Ni (NO 3)2 and hydrate corresponding to the metal ion salt).
3. The method for producing a material NEMOFs containing a bis-azole ligand as claimed in claim 1, wherein the polycyclic azole-rich main ligand in the solution of the polycyclic azole-rich main ligand in the first step is 4,4 '-azo-1, 2, 4-triazole or/and 4,4' -bi-1, 2, 4-triazole.
4. The method for producing a material NEMOFs containing a bis-nitrogen-rich ligand according to claim 1, wherein in the first step, the mono-nitrogen-rich auxiliary ligand in the mono-nitrogen-rich auxiliary ligand solution is one or more of 3, 4-dinitropyrazole, 3, 5-dinitropyrazole and 2, 4-dinitroimidazole.
5. The method for preparing NEMOFs material containing bis-azole ligands according to claim 1, wherein in the second step, the mixing sequence is that the multi-ring azole main ligand solution and the single-ring azole auxiliary ligand solution are mixed first, and then the metal ion salt solution is added.
6. The method for preparing NEMOFs material containing bis-nitrogen-rich ligand according to claim 1, wherein the molar ratio of metal ion salt, polycyclic nitrogen-rich main ligand and monocyclic auxiliary ligand of the three solutions in the second step is 4:1:1-1:1:4.
7. The method for preparing NEMOFs materials containing bis-azole ligands as claimed in claim 1, wherein in the second step, the first portion of the strong acid solution accounts for 1% -10% of the total volume of the solvent;
In the third step, the second part of strong acid solution is 1-10 drops;
The mass concentration of the strong acid solution is one or more of 38% concentrated HCl, 98% concentrated H 2SO4 and 68% concentrated HNO 3.
8. The method for producing a material NEMOFs containing a bis-azole ligand as claimed in claim 1, wherein the stirring temperature in the second step is 40 to 70 ℃ and the stirring time is 0.5 to 2 hours.
9. The method for preparing NEMOFs materials containing a bis-azole ligand according to claim 1, wherein the high-temperature reaction conditions in the third step are: 60-160 deg.c for 2-7 days.
10. NEMOFs material containing a bis-azole ligand prepared by the method of any one of claims 1 to 9.
CN202410110451.4A 2024-01-24 2024-01-24 NEMOFs material containing bisoxazole ligand and preparation method thereof Pending CN117903454A (en)

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