CN111961215B - Light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand and preparation method and application thereof - Google Patents
Light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand, and a preparation method and application thereof, wherein the molecular formula of the material is C50H40N10O13S2Zn2The crystal system is monoclinic, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝100.769°，γ＝90°，
Z is 4; the chemical formula of the material is { Zn (TDC) (PBP). 2.5H2O}nWherein TDC is 3, 5-pyridinedicarboxylic acid, PBP is 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine. The luminescent metal-organic framework material has high-sensitivity detection performance on aromatic nitro explosive 2,4, 6-trinitrophenol.
Description
Technical Field
The invention belongs to the technical field of luminescent crystal materials, and particularly relates to a luminescent metal-organic framework material based on PBP and dicarboxylic acid ligand, and a preparation method and application thereof.
Background
Metal-organic frameworks (MOFs) are a new generation of crystalline porous compounds consisting of metal ions or ion clusters and adjustable organic ligands, which are promising new generation of functional materials due to their extremely high surface area, remarkable physicochemical stability and adjustable pore structure. Recently, light emitting metal-organic frame (LMOFs) sensors have attracted more and more attention due to their excellent sensitivity, high selectivity, and ease of operation. The nitrogen-containing ligand has good metal coordination capability and luminescent property, and is the most common ligand for constructing LMOFs.
Today, the efficient detection of aromatic nitro compounds (NACs) is of great interest due to human health and homeland safety concerns. NACs is a hazardous environmental pollutant because it is not only widely used in a variety of industries, including dyes, fireworks and pharmaceuticals, but it is also difficult to remove or degrade. Therefore, the development of an efficient, rapid, reliable and stable method for detecting NACs has great significance to human health and environment. 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine (PBP) has a plurality of coordination sites, not only contains an internal tridentate N donor which is easily chelated with a metal center, but also has an external N donor which can be combined with the metal center, and has a pi-conjugated skeleton and light-emitting properties. However, no relevant report is found in the research of LMOFs constructed aiming at the ligand for detecting NACs at present.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand, a preparation method and application thereof, and the light-emitting metal-organic framework material has the rapid, simple and convenient and high-sensitivity detection performance on aromatic nitro explosive 2,4, 6-Trinitrophenol (TNP).
The invention is realized by the following technical scheme:
a luminescent metal-organic framework material based on PBP and dicarboxylic acid ligands, the molecular formula of which is C50H40N10O13S2Zn2The crystal system is monoclinic, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝100.769°，γ＝90°，
Z is 4; the chemical formula of the material is { Zn (TDC) (PBP). 2.5H2O}nWherein TDC is 2, 5-thiophenedicarboxylic acid, PBP is 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine, and the structural formula of PBP is as follows:
a method for preparing a light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligands comprises the following steps:
step 1) 0.016g of 0.05mmol PBP and 0.030g of 0.1mmol Zn (NO)3)2·6H2O and 0.017g of 0.1mmol TDC are added into a hydrothermal reaction kettle, and 3mL H is added into the reaction kettle2O and 3mL of DMF, and stirring for 30 min;
step 2) placing the reaction kettle in a drying oven at 90 ℃ for constant-temperature reaction for 72h, and cooling to room temperature at a cooling rate of 2 ℃/h to obtain yellow blocky crystals, namely the light-emitting metal-organic framework material based on the PBP and the dicarboxylic acid ligand, wherein the molecular formula of the yellow blocky crystals is C50H40N10O13S2Zn2。
An application of a light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand as a sensor in detecting 2,4, 6-trinitrophenol.
A fluorescence detector for 2,4, 6-trinitrophenol comprises the light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand.
The invention has the following beneficial effects:
(1) the invention provides a luminescent crystal material { Zn (TDC) (PBP) · 2.5H) capable of detecting TNP in DMF solution with high sensitivity2O}nThe preparation method adopts a hydrothermal synthesis method, has simple synthesis route, easy control, high crystal purity and high yield; the obtained crystalBulk Material { Zn (TDC) (PBP) } 2.5H2O}nThe chemical and optical stability is good, and TNP can be detected by high-sensitivity fluorescence in DMF solution.
(2) The luminescent metal-organic framework material synthesized by the invention has the advantages of simplicity, convenience, rapidness, high sensitivity and the like in the aspect of detecting the aromatic nitro explosive 2,4, 6-Trinitrophenol (TNP).
Drawings
FIG. 1 shows the crystal material { Zn (TDC) (PBP). 2.5H2O}nThe three-dimensional structure diagram of (1);
FIG. 2 shows the crystal material { Zn (TDC) (PBP). 2.5H when 5mM of TNP in DMF is added gradually2O}nA fluorescence intensity map of (a); in fig. 2, the TNP content gradually increases with the direction of the arrow;
FIG. 3 shows the crystal material { Zn (TDC) (PBP). 2.5H2O}nA Stern-Volmer plot against TNP under DMF suspension of (a);
FIG. 4 shows the crystal material { Zn (TDC) (PBP). 2.5H2O}nThe detection limit diagram for TNP under DMF suspension;
FIG. 5 shows the crystal material { Zn (TDC) (PBP). 2.5H2O}nPXRD contrast graph of (a).
Detailed Description
The invention is described in further detail below with reference to specific embodiments and with reference to the following drawings.
Example 1
A preparation method of a light-emitting metal-organic framework material based on PBP and dicarboxylic acid ligand comprises the following specific steps:
(1) weighing PBP (0.016g, 0.05mmol) and Zn (NO)3)2·6H2O (0.030g, 0.1mmol) and TDC (0.017g, 0.1mmol) are measured in terms of H2O (3mL) and DMF (3mL) were added to the hydrothermal reaction kettle and stirred for 30 min.
Wherein TDC is 2, 5-thiophenedicarboxylic acid, PBP is 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine, and the structural formula of PBP is as follows:
(2) then the reaction kettle is put in a drying oven with the temperature of 90 ℃ for constant temperature reaction for 72H, and the temperature is reduced to room temperature at the rate of 2 ℃/H to obtain yellow blocky crystals, namely the luminescent metal-organic framework material based on the PBP and the dicarboxylic acid ligand, which is marked as { Zn (TDC) ((PBP). 2.5H)2O}nCrystal of formula C50H40N10O13S2Zn2。
Elemental analysis measurements (%): c, 50.74; h is 3.39; n is 11.80. Theoretical value (%): c, 50.72; h is 3.41; n is 11.83.
IR(cm-1)：3388(m),3050(w),1627(m),1573(m),1527(m),1336(s),1305(s),1085(s),1035(m),757(m)。
The crystal material { Zn (TDC) (PBP). 2.5H2O}nThe crystallographic data of (a) are shown in table 1 below.
TABLE 1{ Zn (TDC) (PBP) } 2.5H2O}nCrystallographic data sheet of
The single crystal X-ray diffraction results show that: { Zn (TDC) ((PBP). 2.5H)2O}nBelongs to monoclinic system, C2/C space group, and its asymmetric unit is formed from 1 Zn (II), 1 PBP ligand and 1 TDC2-Ligand and 2.5 free water molecules. The Zn centre exhibits a penta-coordination pattern, coordinated by three N atoms from one PBP ligand and two O atoms from two different TDC ligands. The Zn-N bond length ranges are:
a bond length of Zn-O of
And
the major bond lengths and bond angles are listed in table 2 below. Furthermore, the uncoordinated O atom on the TDC ligand forms a hydrogen bond with the carbon atom on the ligand L (C19-H19 … O5, C15-H15 … O7).
TABLE 2{ Zn (TDC) (PBP) } 2.5H2O}nPartial bond length of
And key angle (°) data
{Zn(TDC)(PBP)·2.5H2O}nIn the crystal, the PBP ligand, the TDC ligand and the Zn center are connected to form a 1D chain, and pi-pi accumulation exists between thiophene in the TDC ligand and thiophene in another 1D chain TDC ligand (the distance between the two thiophenes is equal to
) And hydrogen bond (C15-H15 … O7) to connect two 1D chains to form a 1D supramolecular chain structure. The 2D supermolecular structure is formed between chains due to the action of hydrogen bonds (C19-H19 … O5). As shown in FIG. 1, the distance between the surfaces is due to the pi-pi accumulation between the pyrazine and the benzene ring on the PBP ligand (the distance between the pyrazine and the benzene ring is
) And 3D supermolecular structure is formed.
Example 2 crystalline Material { Zn (TDC) (PBP). 2.5H2O}nStudy of fluorescent probing Performance of TNP
3mg of { Zn (TDC) (PBP). 2.5H2O}nDispersing in 30mL DMF solution, ultrasonic treating for 45min, standing for 3d to form stable suspension as standard suspension, and mixing 5mmol 2,4, 6-trinitrobenzenePhenol (TNP), titrated gradually to { Zn (TDC) (PBP) } 2.5H2O}nThe luminescence intensity of the suspension was monitored and recorded in DMF, and as shown in FIG. 2, the luminescence intensity of the suspension was significantly reduced after TNP addition, and almost disappeared when 40. mu.L of TNP was added dropwise, and the quenching efficiency reached 92.6%.
Quenching efficiency can be obtained by Stern-Volmer equation I0/I＝1+Ksv[M]Quantitative analysis, as shown in FIG. 3, { Zn (TDC) (PBP) · 2.5H2O}nQuenching constant (K) for TNPsv) Is 5.832X 104M-1{ Zn (TDC) (PBP). 2.5H is illustrated2O}nHas high quenching capacity to TNP. As shown in Table 3 below, { Zn (TDC) (PBP). 2.5H2O}nK to TNPsvAlso higher than the reported luminescent metal-organic framework materials.
TABLE 3 reported LMOFs and { Zn (TDC) ((PBP) · 2.5H)2O}nQuenching constants for detecting TNP in DMF suspension
The limit of detection (LOD) can be calculated by the formula 3 σ/K (σ: standard deviation, K: slope). As shown in FIG. 4, { Zn (TDC) ((PBP) & 2.5H) is obtained by calculation2O}nThe limit of detection for TNP is 1.731X 10-3And mM. This indicates { Zn (TDC) (PBP) } 2.5H2O}nHas high sensitivity to TNP detection.
FIG. 5 shows the crystal material { Zn (TDC) (PBP). 2.5H2O}nPowder X-ray diffraction pattern of (1). As can be seen from FIG. 5, the crystalline material { Zn (TDC) ((PBP) · 2.5H) was produced2O}nThe powder X-ray diffraction pattern is basically consistent with the X-ray diffraction pattern calculated by theory, which shows that the crystal material prepared by the invention has high purity. Meanwhile, the X-ray diffraction pattern of the prepared crystal material after being soaked in TNP for one day and in DMF solution for one week is basically consistent with the X-ray diffraction pattern calculated by theory, which indicates that the prepared crystal material has the X-ray diffraction pattern in TNP and DMF solutionGood stability.
Claims (4)
1. A luminescent metal-organic framework material based on PBP and dicarboxylic acid ligands, characterized in that the molecular formula of the material is C50H40N10O13S2Zn2The crystal system is monoclinic, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝100.769°，γ＝90°，
Z is 4; the chemical formula of the material is { Zn (TDC) (PBP). 2.5H2O}nWherein TDC is 2, 5-thiophenedicarboxylic acid, PBP is 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine, and the structural formula of PBP is as follows:
2. the method of claim 1, comprising the steps of:
step 1) 0.016g of 0.05mmol PBP and 0.030g of 0.1mmol Zn (NO)3)2·6H2O and 0.017g of 0.1mmol TDC are added into a hydrothermal reaction kettle, and 3mL H is added into the reaction kettle2O and 3mL of DMF, and stirring for 30 min;
step 2) placing the reaction kettle in a drying oven at 90 ℃ for constant-temperature reaction for 72h, and cooling to room temperature at a cooling rate of 2 ℃/h to obtain yellow blocky crystals, namely the light-emitting metal-organic framework material based on the PBP and the dicarboxylic acid ligand, wherein the molecular formula of the yellow blocky crystals is C50H40N10O13S2Zn2。
3. Use of a PBP and dicarboxylic acid ligand based luminescent metal-organic framework material as described in claim 1 as a sensor for the detection of 2,4, 6-trinitrophenol.
4. A fluorescence detector for 2,4, 6-trinitrophenol, characterized by comprising a luminescent metal-organic framework material based on PBP and dicarboxylic acid ligands according to claim 1.
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