CN115746326A - Photostimulation responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene guest - Google Patents
Photostimulation responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene guest Download PDFInfo
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Abstract
Aiming at the shortage that the ordered encapsulation of the object is utilized to construct the photostimulation responsive rare earth metal organic framework, the invention provides the photostimulation responsive europium-based metal organic framework (TTF @ Eu-MOF) for the ordered encapsulated tetrathiafulvalene object through the exploration of a synthesis method. The TTF @ Eu-MOF is synthesized by taking self-prepared Eu-MOF as a precursor through soaking in tetrathiafulvalene solution. TTF molecules are orderly arranged in the pore channel of the framework and form rich pi \823030witha naphthalene diimide matrix of the ligand, and pi stacking interaction is realized. Under the external light stimulation, ultraviolet and fluorescence signals of TTF @ Eu-MOF are changed, obvious responsiveness is presented, and the potential of developing the TTF @ Eu-MOF into light stimulation responsive molecular base materials is achieved.
Description
Technical Field
The invention belongs to the field of stimuli-responsive molecular-based materials, and particularly relates to an assembly method and application of a photostimulation-responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene guests.
Background
In the leading research of new materials, photostimulation responsive molecule-based materials are one of the favored types. The material has the inherent advantages of light weight, convenient processing and forming, easy regulation and modification and the like of molecular base materials. More importantly, the material can regulate and control the performance in a remote, non-invasive and rapid mode through a light stimulation means, is very helpful for device formation and intellectualization in the application process, and is one of rational materials for manufacturing intelligent devices.
Compared with organic small molecules and macromolecules, metal Organic Frameworks (MOFs) combine the characteristics of metal ions and organic ligands at the same time, can integrate other additional functions through the inherent framework characteristics, and play an important role in the research and development of photostimulation responsive molecular base materials.
However, the vast majority of the currently reported or developed photostimulation-responsive MOFs focus on transition metal MOFs. There is still less research on photostimulation responsive rare earth MOFs. On the other hand, most of the currently reported photostimulation-responsive MOFs are constructed by photochemical activity of their own host framework (metal center or ligand). There are relatively few MOFs that exploit the interaction of in-frame objects with the host frame to build photostimulation response mechanisms. The object exists orderly in the frame and has rare earth MOFs with photostimulation responsiveness, and at present, few related reports exist.
Disclosure of Invention
Aiming at the current situation, the invention develops a photostimulation responsive europium-based metal organic framework (hereinafter referred to as TTF @ Eu-MOFs) for orderly packaging tetrathiafulvalene guest, and provides an assembly method and related application thereof.
The invention relates to TTF @ Eu-MOF, which is characterized in that: its chemical composition is [ Eu 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]·2TTF·2DMF·2H 2 O, wherein NDI-H 2 SaA is an N, N' -bis (5-salicyloyl) naphthalimide ligand and TTF stands for tetrathiafulvalene. The TTF @ Eu-MOF is crystalline, and crystals thereof are crystallized in a triclinic system
Space group, the main crystallographic parameters are:
α＝64.7270(1)°，β＝68.2370(1)°，γ＝76.2690(1)°；
Z＝1，ρ calc (g/cm 3 )＝1.697g·cm -3 ，μ＝1.399mm -1 ，F(000)＝1428.0。
specific crystallographic data are shown in table 1 below:
TABLE 1 crystallographic parameters of TTF @ Eu-MOF
The invention relates to an assembly method of TTF @ Eu-MOF, which comprises the following specific steps:
(1) 1,4,5, 8-naphthalene tetracarboxylic anhydride (10 mmol, 2.68g) and 5-aminosalicylic acid (20 mmol, 3.06g) were weighed and charged into a 100mL single-neck round-bottom flask containing 60mL of N, N-Dimethylformamide (DMF). The flask was placed in an oil bath at 155 ℃ and stirred under reflux for 12 hours, and then naturally cooled to room temperature. And (4) carrying out suction filtration on the orange powdery precipitate separated out from the solution, repeatedly washing the orange powdery precipitate by using anhydrous methanol, and naturally drying the orange powdery precipitate at normal temperature. Obtaining the N, N' -bis (5-salicyloyl) naphthalimide ligand (NDI-H) for preparing the TTF @ Eu-MOF 2 SaA)。
(2) Weighing NDI-H 2 SaA ligand (0.068mmol, 17.1mg) and EuCl 3 ·6H 2 O (0.045mmol, 36.0 mg) was placed in a 15mL glass microtube and 6mL DMF was added. After magnetic stirring for 45min, the mixture was sealed and placed in an oven at 100 ℃. And after 72h of reaction, cooling to room temperature at a gradient of 4 ℃/h to obtain a precursor Eu-MOF for preparing TTF @ Eu-MOF.
(3) Preparing 0.1mol/L TTF methanol solution. The precursor Eu-MOF (20 mg) prepared above was added to a TTF methanol (10 mL) solution and transferred to a vessel suitable for slow solvent evaporation. The solvent was kept slowly evaporating at room temperature. The light green blocky crystals of TTF @ Eu-MOF according to the invention can be obtained after about 3 weeks.
The TTF @ Eu-MOF is structurally characterized in that:
the TTF @ Eu-MOF is composed of [ Eu 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]And (4) a structural unit. 2 Eu of the unit III The ion firstly consists of 1 (NDI-H) 2 SaA) 2- The ligand is expressed as mu 2 -η 1 :η 2 Mode-bridged, and each Eu III The ion is connected with 1 mu 2 -η 1 :η 2 Of coordination mode (NDI-H) 2 SaA) 2- Connected, thereby forming a "C" shaped cell topology. Adjacent C-shaped cells are arranged in the same direction, each cell passing through 2 μ 2 -η 1 :η 2 Of coordination mode (NDI-H) 2 SaA) 2- Ligand is linked to another unit, thereby forming a ligand of [ Eu ] 4 ]An elliptical ring-shaped one-dimensional ladder-shaped frame which is periodically arranged. The TTF guest successfully introduced is right through each [ Eu ] along the direction of the b-axis 4 ]Elliptical rings, forming an ordered arrangement. Also, TTF guest and moiety (NDI-H) 2 SaA) 2- The NDI parent body of the ligand forms stronger pi \8230, pi accumulation effect.
The invention has the advantages that:
based on the current situation that the existing photostimulation responsive rare earth MOFs are still few, particularly aiming at the scarcity of constructing photostimulation responsive rare earth MOFs by ordered packaging of ordered objects, the photostimulation responsive Eu-MOFs with a TTF object in ordered packaging is successfully introduced through a specific assembly method. The invention has stronger originality, provides a novel photostimulation responsive molecular base material and an assembly method thereof, and simultaneously provides effective reference for the design and synthesis of photostimulation rare earth MOFs based on a host-guest system.
Drawings
FIG. 1 shows N, N' -bis (5-salicyloyl) naphthalimide ligand (NDI-H) used in the present invention 2 SaA) structural diagram of the ligand.
FIG. 2 is [ Eu ] of TTF @ Eu-MOF according to the present invention 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]The structural units are combined into a diagram.
FIG. 3 is a one-dimensional framework diagram of TTF @ Eu-MOF according to the present invention.
FIG. 4 is an X-ray powder diffraction pattern of TTF @ Eu-MOF according to the present invention.
FIG. 5 is a UV spectrum of TTF @ Eu-MOF before and after photo-stimulation in the present invention.
FIG. 6 is a fluorescence emission spectrum of TTF @ Eu-MOF according to the present invention before and after photo-stimulation.
Detailed Description
Example (b):
1. the invention relates to an assembly method of TTF @ Eu-MOF, which comprises the following steps:
(1) 1,4,5, 8-naphthalene tetracarboxylic anhydride (10 mmol, 2.68g) and 5-aminosalicylic acid (20 mmol, 3.06g) were added to a 100mL single neck round bottom flask containing 60mL of N, N-Dimethylformamide (DMF). The flask was placed in an oil bath and heated to 155 ℃ with stirring to reflux. As the reaction proceeded, a large amount of orange solid began to form in the tan solution. And continuously keeping the reflux for 12 hours, removing the oil bath pot, naturally standing the reaction solution, and cooling to room temperature. Filtering the orange powdery precipitate, repeatedly washing with anhydrous methanol, and naturally drying at room temperature to obtain N, N' -bis (5-salicyloyl) naphthalimide ligand (NDI-H) 2 SaA). The ligand structure is shown in figure 1.
(2) According to the molar equivalent of 1.5 2 SaA ligand (0.0675mmol, 17.1mg) and rare earth metal salt EuCl 3 ·6H 2 O (0.045mmol, 36.0 mg) was put in a 15mL glass sample bottle, 6mL DMF was added, and the mixture was stirred at normal temperature and pressure for 45min and then sealed quickly. And then, preheating an oven to 100 ℃, quickly transferring the mixed reaction liquid into the oven after uniformly stirring, reacting for 72 hours, cooling to room temperature at a gradient of 4 ℃/h, and taking out from the oven to obtain a light yellow transparent blocky crystal precursor for TTF @ Eu-MOF assembly.
(3) Preparing 0.1mol/L TTF methanol solution for later use. Subsequently, 20mg of the crystal precursor synthesized above was weighed, added to 10mL of TTF methanol solution, sealed and soaked in a dark environment for several days. After the soaking is kept for about 3 weeks, the light green blocky crystals of TTF @ Eu-MOF are obtained. The yield was about 42% based on precursor.
2. The crystal structure of TTF @ Eu-MOF is characterized in that:
the single crystal structure of the frame was tested using a Rigaku OD Smartlab SE single crystal diffractometer using a graphite monochromatized Mo-Ka radiation source at 193.0K
Data were collected by the cryslalispro program in the manner of Omega scan. And determining a Laue cluster and an initial space cluster of the data by using XPREP, using a SHLEXT program to analyze phases, deducing the space cluster by using a phase analysis method, and building an initial model according to an electron density map as much as possible. After obtaining the rough structure, primarily refining the structure by using a SHELXL program, then correcting all non-hydrogen atoms by adopting anisotropic refining, correcting the hydrogen atoms by adopting isotropic thermal parameters, hydrogenating by adopting a theoretical hydrogenation mode, and finally refining the structure repeatedly by using the SHELXL program for a plurality of times until the goodness of fit (GooF value) and a residual factor (R) are obtained 1 Value) to within the theoretical value range. And calculating pi \8230inthe framework through PLATON, and calculating pi stacking interaction and hydrogen bonding interaction.
As shown in FIG. 2, the TTF @ Eu-MOF consists of [ Eu 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]And (4) a structural unit. 2 Eu of the unit III The ion firstly consists of 1 (NDI-H) 2 SaA) 2- The ligand is expressed in μ 2 -η 1 :η 2 Mode-bridged, and each Eu III The ion is connected with 1 mu 2 -η 1 :η 2 Of coordinated mode (NDI-H) 2 SaA) 2- Connected, thereby forming a "C" shaped cell topology. Adjacent C-shaped units are arranged in the same direction and each unit passes throughIt contains 2 μ 2 -η 1 :η 2 Of coordinated mode (NDI-H) 2 SaA) 2- Ligand is linked to another unit, thereby forming a ligand of [ Eu ] 4 ]An elliptical ring-shaped one-dimensional ladder-shaped frame (figure 3) which is periodically arranged. Two Eu in the dual-core node are calculated by Shape2.0 program Ⅲ All ions are in eight-coordination environment and present D 2d A symmetrical trigonal dodecahedron coordination geometry. The TTF guest successfully introduced is right through each [ Eu ] along the direction of the b-axis 4 ]Elliptical rings, forming an ordered arrangement. Meanwhile, TTF guest and moiety (NDI-H) 2 SaA) 2- The NDI parent of the ligand forms stronger pi \8230andpi accumulation.
3. The X-ray powder diffraction characterization of TTF @ Eu-MOF provided by the invention is as follows:
as shown in FIG. 4, the powder diffraction curve obtained by the TTF @ Eu-MOF test matches well with the curve simulated by single crystal data.
4. The photostimulation responsiveness of TTF @ Eu-MOF provided by the invention is as follows:
FIG. 5 shows the constant external xenon lamp cold light source irradiation distance 1cm and the constant external xenon lamp cold light source irradiation intensity 343.5mW/cm for TTF @ Eu-MOF 2 Under the condition of light radiation, ultraviolet spectrograms are measured after different time of irradiation. The obvious change of the ultraviolet spectrum curve can be visually observed, and a new ultraviolet characteristic absorption peak is generated in the wavelength range of 380-400 nm. FIG. 6 shows that the frame is positioned at the irradiation distance of 1cm and the illumination intensity of 343.5mW/cm of the constant exogenous xenon lamp cold light source 2 Under the condition of light radiation, the fluorescence emission spectrogram measured after different time of irradiation. The results showed that the fluorescence intensity at 621nm showed a tendency to decrease in a short time, but the fluorescence intensity increased abruptly after the light irradiation time increased to some extent, and then continued to show a tendency to decrease. These results indicate that the TTF @ Eu-MOF shows obvious responsiveness under light stimulation, and can be developed and utilized as a potential light stimulation responsive molecular material.
Claims (8)
1. A photostimulation responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene guest is characterized in thatThen, its chemical composition is [ Eu ] 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]·2TTF·2DMF·2H 2 O, wherein NDI-H 2 SaA is an N, N' -bis (5-salicyloyl) naphthalimide ligand, and TTF represents tetrathiafulvalene.
2. The photostimulation-responsive europium-based metal-organic framework of claim 1, wherein said framework is crystallized in a triclinic system
Space group, the main crystallographic parameters of which are:
α＝64.7270(1)°，β＝68.2370(1)°，γ＝76.2690(1)°；
Z＝1，ρ calc (g/cm 3 )＝1.697g·cm -3 ，μ＝1.399mm -1 ，F(000)＝1428.0。
3. the photostimulation-responsive europium-based metal organic framework for ordered encapsulation of tetrathiafulvalene guest according to claim 1, wherein the host framework has the structural characteristics of: 2 Eu pieces III The ion firstly consists of 1 (NDI-H) 2 SaA) 2- The ligand is expressed as mu 2 -η 1 :η 2 Mode-bridged, and each Eu III The ion is connected with 1 mu 2 -η 1 :η 2 Of coordinated mode (NDI-H) 2 SaA) 2- Thereby forming "C" -shaped [ Eu 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]A structural unit; adjacent C-shaped cells are arranged in the same direction, each cell passing through 2 μ 2 -η 1 :η 2 Of coordination mode(NDI-H 2 SaA) 2- Ligand is linked to another unit, thereby forming a ligand of [ Eu ] 4 ]The elliptical rings are periodically arranged to form a one-dimensional ladder-shaped frame.
4. The photostimulation-responsive europium-based metal-organic framework of claim 1, with an ordered encapsulated tetrathiafulvalene guest characterized by the TTF guest: the introduced TTF objects form ordered arrangement in the grid of the frame along the direction of the b axis; meanwhile, TTF guest and moiety (NDI-H) 2 SaA) 2- The NDI parent of the ligand forms stronger pi \8230andpi accumulation.
5. A method for preparing a photostimulation-responsive europium-based metal organic framework for orderly encapsulating tetrathiafulvalene guest as claimed in claims 1-4, which is characterized in that the prepared precursor Eu-MOF (20 mg) is added into TTF methanol (0.1 mol/L;10 mL) solution and transferred into a container suitable for slow solvent evaporation; at room temperature, the solvent was kept slowly evaporating.
6. The preparation method according to claim 5, wherein the precursor Eu-MOF is prepared by the following specific processes: weighing NDI-H 2 SaA ligand (0.0675mmol, 17.1mg) and EuCl 3 ·6H 2 O (0.045mmol, 36.0 mg) is placed in a 15mL sample bottle, 6mL DMF is added, and the mixture is stirred for 45min at normal temperature and pressure and then sealed; and after the mixed reaction liquid is uniformly stirred, quickly transferring the mixed reaction liquid into a 100 ℃ oven, reacting for 72 hours, and then cooling to room temperature at a gradient of 4 ℃/h.
7. The method according to claim 6, wherein the NDI-H is a reaction raw material 2 SaA and EuCl 3 ·6H 2 The dosage of O is 0.0675mmol and 0.045mmol respectively, and the molar ratio is 3: 1; the reaction solvent was DMF and the total volume was 6mL.
8. The photostimulation-responsive europium-based metal organic framework for ordered encapsulation of tetrathiafulvalene guest of claim 1, wherein the photostimulation-responsiveness is characterized by: under the stimulation of exogenous light, the ultraviolet spectrum and the fluorescence spectrum of the fluorescent material are changed, and the responsiveness is shown.
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