CN115746326B - Light stimulus response europium-based metal organic framework for orderly packaging tetrathiafulvalene object - Google Patents
Light stimulus response europium-based metal organic framework for orderly packaging tetrathiafulvalene object Download PDFInfo
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- CN115746326B CN115746326B CN202211543450.6A CN202211543450A CN115746326B CN 115746326 B CN115746326 B CN 115746326B CN 202211543450 A CN202211543450 A CN 202211543450A CN 115746326 B CN115746326 B CN 115746326B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
Abstract
Aiming at the scarcity of the light stimulus response rare earth metal organic framework constructed by utilizing ordered encapsulation of objects, the invention provides the light stimulus response europium-based metal organic framework (TTF@Eu-MOF) for ordered encapsulation of tetrathiafulvalene objects through innovation of a synthesis method. The TTF@Eu-MOF is synthesized by taking self-prepared Eu-MOF as a precursor through a tetrathiafulvalene solution impregnation method. Wherein TTF molecules are orderly arranged in pore channels of the framework and form rich pi … pi stacking interactions with naphthalimide precursors of the ligand. Under the external light stimulus, the ultraviolet and fluorescent signals of TTF@Eu-MOF are changed, obvious responsiveness is presented, and the material has the potential of being developed into a light stimulus responsive molecular base material.
Description
Technical Field
The invention belongs to the field of stimulus-responsive molecular base materials, and in particular relates to an assembly method and application of a light stimulus-responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene objects.
Background
In the leading edge of research on new materials, photo-stimulus-responsive molecular-based materials are one of the favored types. The material has the advantages inherent to the molecular material, such as light weight, convenient processing and forming, easy regulation and modification. 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 beneficial to the device and the 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, and can integrate other additional functions through the inherent framework characteristics, so that the MOFs take an important role in research and development of light stimulus response molecule-based materials.
However, the most recently reported or developed light stimulus responsive MOFs have focused on transition metal MOFs. There is still little research on light stimulus responsive rare earth MOFs. On the other hand, most of the currently reported photo-stimulus-responsive MOFs have been constructed by photochemically active sources of their own host frameworks (metal centers or ligands). MOFs that utilize the interaction of an intra-framework guest with a host framework to build a light stimulus response mechanism are relatively few. The object exists orderly in the framework, and has rare earth MOFs with light stimulus response, so few related reports exist at present.
Disclosure of Invention
The invention aims at the current situation, and develops a light stimulus response europium-based metal organic framework (TTF@Eu MOFs) for orderly packaging tetrathiafulvalene objects, and provides an assembly method and related application thereof.
The TTF@Eu-MOF disclosed by the invention is characterized in that: the chemical composition of the catalyst is [ Eu ] 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]·2TTF·2DMF·2H 2 O, where NDI-H 2 SaA is an N, N' -bis (5-salicyl) naphthalimide ligand and TTF represents tetrathiafulvalene. The TTF@Eu-MOF is crystalline and the crystal is crystallized in a triclinic systemSpace group, its 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 assembling method of the TTF@Eu-MOF comprises the following specific steps:
(1) 1,4,5, 8-naphthalene tetracarboxylic anhydride (10 mmol,2.68 g) and 5-aminosalicylic acid (20 mmol,3.06 g) were weighed 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 refluxed with stirring for 12 hours, and then cooled naturally to room temperature. The orange powder precipitate precipitated in the solution is filtered by suction, repeatedly washed with absolute methanol, and naturally dried at normal temperature. Obtaining N, N' -bis (5-salicyl) naphthalimide ligand (NDI-H) for preparing TTF@Eu-MOF according to the present invention 2 SaA)。
(2) Weighing NDI-H 2 SaA ligand (0.068 mmol,17.1 mg) with EuCl 3 ·6H 2 O (0.045 mmol,36.0 mg) was placed in a 15mL glass micropin and 6mL DMF was added. After magnetic stirring for 45min, it was sealed and placed in an oven at 100 ℃. And (3) cooling to room temperature with a gradient of 4 ℃/h after reacting for 72h to obtain a precursor Eu-MOF for preparing the TTF@Eu-MOF.
(3) A0.1 mol/L methanol solution of TTF was prepared. The precursor Eu-MOF (20 mg) prepared above was added to a solution of TTF in methanol (10 mL) and transferred to a container suitable for slow evaporation of the solvent. At room temperature, the solvent was kept slowly volatile. After about 3 weeks, the light green blocky crystal of TTF@Eu-MOF can be obtained.
The TTF@Eu-MOF disclosed by the invention is characterized in that:
the TTF@Eu-MOF is formed by [ Eu ] 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]The structural unit is formed. 2 Eu of the unit III The ions are first formed from 1 (NDI-H 2 SaA) 2- Ligand in mu 2 -η 1 :η 2 Mode bridging of Eu III Ion is re-connected with 1 mu 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- And connected to form a "C" shaped cell. Adjacent C-shaped units are arranged in the same direction, and each unit comprises 2 mu units 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- The ligand is linked to another unit, thereby forming a ligand [ Eu ] 4 ]Oval ring shape periodic arrangement one-dimensional ladder frame. The successfully incorporated TTF object passes right through each Eu along the direction of the b axis 4 ]Oval rings, forming an ordered arrangement. At the same time, TTF object and moiety (NDI-H) 2 SaA) 2- The NDI matrix of the ligand forms a stronger pi … pi stacking effect.
The invention has the advantages that:
the invention is based on the current situation that the existing light stimulus response rare earth MOFs are still less, and particularly aims at the scarcity of the rare earth MOFs which are constructed to have light stimulus response by utilizing ordered encapsulation of ordered objects, and the Eu-MOFs which are ordered and encapsulated with TTF objects and have light stimulus response are successfully introduced by a specific assembly method. The invention has stronger originality, provides a novel light stimulus response molecular base material and an assembling method thereof, and simultaneously provides effective reference for the design and synthesis of light stimulus rare earth MOFs based on a host-guest system.
Drawings
FIG. 1 is a diagram of N, N' -bis (5-salicyl) naphthalimide ligand (NDI-H) used in the present invention 2 SaA) ligand structure diagram.
FIG. 2 shows the TTF@Eu-MOF [ Eu ] of the present invention 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]Structural unit composition diagram.
FIG. 3 is a one-dimensional frame diagram of TTF@Eu-MOF in the present invention.
FIG. 4 is a powder X-ray diffraction pattern of TTF@Eu-MOF in accordance with the present invention.
FIG. 5 is a graph of ultraviolet spectra of TTF@Eu-MOF before and after optical stimulus in accordance with the present invention.
FIG. 6 is a graph showing fluorescence emission spectra of TTF@Eu-MOF before and after optical excitation in the present invention.
Detailed Description
Examples:
1. the assembling method of the TTF@Eu-MOF comprises the following specific steps:
(1) 1,4,5, 8-naphthalene tetracarboxylic anhydride (10 mmol,2.68 g) and 5-aminosalicylic acid (20 mmol,3.06 g) were charged 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 under reflux at 155 ℃. As the reaction proceeds, a significant amount of orange solid begins to form in the tan solution. After the reflux is continued for 12 hours, the oil bath is removed, the reaction liquid is naturally stood still, and the reaction liquid is cooled to room temperature. Filtering the orange powder precipitate, repeatedly washing with anhydrous methanol, and naturally drying at room temperature to obtain N, N' -bis (5-salicyl) naphthalimide ligand (NDI-H) 2 SaA). The ligand structure is shown in figure 1.
(2) NDI-H was weighed out in a molar equivalent of 1.5:1 2 SaA ligand (0.0675 mmol,17.1 mg) with EuCl 3 ·6H 2 O (0.045 mmol,36.0 mg) was placed in a 15mL glass sample bottle, 6mL DMF was added, and the mixture was stirred at room temperature and pressure for 45min and then sealed rapidly. And then preheating the oven to 100 ℃, quickly transferring the mixed reaction liquid into the oven after the mixed reaction liquid is uniformly stirred, cooling to room temperature with a gradient of 4 ℃ per hour after reacting for 72 hours, and taking out the reaction liquid from the oven to obtain the pale yellow transparent bulk crystal precursor for TTF@Eu-MOF assembly.
(3) Preparing 0.1mol/L TTF methanol solution for standby. Subsequently, 20mg of the synthesized crystal precursor was weighed, added to 10mL of TTF methanol solution, sealed and immersed in a dark environment for several days. After the crystal is soaked for about 3 weeks, the light green blocky crystal of TTF@Eu-MOF provided by the invention can be obtained. The yield was about 42% based on the precursor.
2. The crystal structure of the TTF@Eu-MOF provided by the invention is characterized by:
the single crystal structure of the frame was tested using a Rigaku OD Smartlab SE single crystal diffractometer using a graphite-monochromatized Mo-K alpha radiation diffraction source at 193.0KData were collected by the CrysalisPro program in the manner of Omega scan. The Laue group and the initial space group of the data are determined by XPREP, the Laue group and the initial space group are used for resolving phases through SHLEXT program, the space group is inferred by using a phase resolving method, and an initial model is built according to an electron density map to the greatest possible extent. After obtaining the rough structure, the structure is primarily refined by using the SHELXL program, all non-hydrogen atoms are then corrected by adopting anisotropic refinement, the hydrogen atoms are corrected by adopting isotropic thermal parameters and hydrogenated by adopting a theoretical hydrogenation mode, and finally the structure is repeatedly refined for a plurality of times by using the SHELXL program until the fitting goodness (GooF value) and residual factors (R) 1 Value) of the two important parameters to be within the theoretical value. Pi … pi stacking interactions and hydrogen bonding in this framework were calculated by PLATON.
As shown in FIG. 2, the TTF@Eu-MOF is defined by [ Eu ] 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]The structural unit is formed. 2 Eu of the unit III The ions are first formed from 1 (NDI-H 2 SaA) 2- Ligand in mu 2 -η 1 :η 2 Mode bridging of Eu III Ion is re-connected with 1 mu 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- And connected to form a "C" shaped cell. Adjacent C-shaped units are arranged in the same direction, and each unit comprises 2 mu units 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- The ligand is linked to another unit, thereby forming a ligand [ Eu ] 4 ]Oval rings are periodically arranged in one dimension in a ladder-like frame (fig. 3). As known from the shape2.0 program calculation, two Eu in the dual-core node Ⅲ The ions are all in eight-coordination environment to present D 2d Symmetrical triangular dodecahedron coordination geometry. The successfully incorporated TTF object passes right through each Eu along the direction of the b axis 4 ]Oval rings, forming an ordered arrangement. At the same time, TTF object and moiety (NDI-H) 2 SaA) 2- The NDI matrix of the ligand forms a stronger pi … pi stacking effect.
3. X-ray powder diffraction characterization of TTF@Eu-MOF:
as shown in fig. 4, the powder diffraction curve obtained by the ttf@eu-MOF test matches well with the curve obtained by simulation with single crystal data.
4. The TTF@Eu-MOF provided by the invention has the following photo-stimulus responsiveness:
FIG. 5 shows the illumination distance of TTF@Eu-MOF at a constant exogenous xenon lamp cold light source of 1cm and the illumination intensity of 343.5mW/cm 2 And (3) irradiating ultraviolet spectrograms measured after different times. From this figure, it can be seen that the ultraviolet spectrum of TTF@Eu-MOF varies significantly and a new ultraviolet characteristic absorption peak is generated in the wavelength range of 380-400 nm. FIG. 6 shows the illumination distance of TTF@Eu-MOF at a constant exogenous xenon lamp cold light source of 1cm and the illumination intensity of 343.5mW/cm 2 And (3) irradiating the fluorescent emission spectrum measured after different times. The result showed that the fluorescence intensity at 621nm showed a tendency to decrease in a short time, but after the light irradiation time increased to a certain extent, the fluorescence intensity was steeply increased, and then continued to show a tendency to decrease. These results indicate that the TTF@Eu-MOF exhibits obvious responsiveness under light stimulation, and can be developed and utilized as a potential light-stimulus responsive molecular material.
Claims (6)
1. A light stimulus responsive europium-based metal organic framework for orderly packaging tetrathiafulvalene object comprises the chemical composition of [ Eu ] 2 (NDI-H 2 SaA) 3 (DMF) 2 (H 2 O) 4 (CH 3 OH) 2 ]·2TTF·2DMF·2H 2 O, where NDI-H 2 SaA isN,N’-bis (5-salicyl) naphthalimide ligand, while TTF stands for tetrathiafulvalene; the metal organic framework is crystallized in a triclinic systemP Space group, its main crystallographic parameters are:a = 13.2889(4) Å，b = 15.0752(4) Å，c = 16.4754(5) Å；α = 64.7270(1)°，β = 68.2370(1)°，γ = 76.2690(1)°；V = 2759.50(1) Å 3 ，Z = 1，ρ calc = 1.697 g∙cm -3 ，μ = 1.399 mm -1 ，F(000) = 1428.0。
2. the light stimulus-responsive europium-based metal-organic framework for orderly encapsulating a tetrathiafulvalene guest of claim 1, wherein the host framework is characterized by: 2 Eu III The ions are composed of 1 (NDI-H) 2 SaA) 2- Ligandsμ 2 -η 1 :η 2 Mode bridging of Eu III Ion is connected with 1μ 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- Thereby forming a 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 units are arranged in the same direction, each unit comprises 2 unitsμ 2 -η 1 :η 2 Coordination mode (NDI-H) 2 SaA) 2- The ligand is linked to another unit, thereby forming a ligand [ Eu ] 4 ]The elliptical rings are arranged in a one-dimensional ladder-shaped frame periodically.
3. A light stimuli responsive europium-based metal organic framework in which tetrathiafulvalene guests are encapsulated in order as claimed in any one of claims 1 to 2, the TTF guest being characterised by: the TTF object is introduced alongbThe direction of the shaft forms an ordered arrangement among the grids of the frame; at the same time, TTF object and moiety (NDI-H) 2 SaA) 2- The NDI matrix of the ligand forms a stronger pi ∙ ∙ ∙ pi stacking effect.
4. The light stimulus-responsive europium-based metal organic framework of any one of claims 1-2, which comprises the following specific characteristics: under the exogenous light stimulus, the ultraviolet and fluorescence spectrums of the fluorescent dye change, and the fluorescent dye shows responsiveness.
5. The method for preparing the light stimulus response europium-based metal organic framework for orderly encapsulating tetrathiafulvalene object according to any one of claims 1 to 4, which comprises the following specific processes: the prepared 20mg precursor Eu-MOF is added into 10mL and 0.1mol/L TTF methanol solution and transferred into a container suitable for slow solvent volatilization; at room temperature, the solvent was kept slowly volatile.
6. The preparation method according to claim 5, wherein the preparation method of the precursor Eu-MOF comprises the following specific steps: weighing 0.0675mmol of NDI-H according to a molar ratio of 1.5:1 2 SaA ligand with 36.0mg EuCl 3 ·6H 2 O, placing in a sample bottle of 15mL, adding 6mL of DMF, stirring for 45min at normal temperature and normal pressure, and sealing; and (3) after the mixed reaction liquid is uniformly stirred, rapidly transferring the mixed reaction liquid into a 100 ℃ oven, and cooling to room temperature by 4 ℃/h gradient after reacting 72 and h.
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