CN114621455B - Metal organic framework material of pentacene derivative and application - Google Patents

Metal organic framework material of pentacene derivative and application Download PDF

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CN114621455B
CN114621455B CN202210244639.9A CN202210244639A CN114621455B CN 114621455 B CN114621455 B CN 114621455B CN 202210244639 A CN202210244639 A CN 202210244639A CN 114621455 B CN114621455 B CN 114621455B
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唐蜜
王正帮
孙浩
苏轮
薛萍
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Abstract

The invention provides a pentacene derivative metal organic framework material and application, belongs to the field of organic photoelectric and electromagnetic functional materials, and comprises a part formed by complexing a pentacene derivative ligand and a metal atom, wherein the pentacene derivative ligand is a compound substituted by a 6, 13-dimethylene-6, 13-dihydropentacene tetra-aromatic ring at the 6, 13-position, and has a four-class structural general formula. The material structure of the invention is constructed based on pentacene derivatives, and due to the introduction of acene, a large pi-conjugated system is constructed, so that the MOF has good crystallinity, conductivity and fluorescence characteristics, and the material can be used for preparing various sensitive sensors.

Description

Metal organic framework material of pentacene derivative and application
Technical Field
The invention belongs to the field of organic photoelectric and electromagnetic functional materials, and particularly relates to a pentacene derivative metal organic framework material and application thereof.
Background
The Metal Organic Frameworks (MOFs) are composed of organic ligands and inorganic nodes, and are porous crystal materials which have high specific surface area, adjustable functions and pore diameters and can be used for designing framework topology. Due to its excellent properties, MOFs materials are receiving more and more attention in the fields of gas separation and adsorption, biomedicine, sensing, luminescence, energy storage, separation, catalysis, and the like. However, the large spatial distance between the ligand and the metal center in the MOF structure hinders the transport of charge through space, and coupled with the delocalization limitation of the resonances of adjacent metal clusters, the conductivities of most MOFs are reduced (<10 -10 S cm -1 ) And the development of the MOF material in the electronic field is hindered, so that the improvement of the MOF material is needed, the conductivity of the MOF material is improved, and the application range of the MOF material is widened.
Two-dimensional pi-conjugated metal-organic framework materials are hot spots for conducting MOFs research in recent years. Most of the materials are connectors containing benzene/benzophenanthrene derivatives, honeycomb stacked lattices are displayed, and N, O and S contained in ligands provide coordination environments for metal nodes. Compared with other MOFs, the charge delocalization and the expanded pi conjugation in the plane of the two-dimensional pi metal-organic framework material show high charge carrier mobility and high conductivity, and the material has potential application in the fields of electrochemistry and sensing. Therefore, the synthesis of the two-dimensional pi-conjugated metal-organic framework material has important significance for researching conductive MOFs.
Pentacene structure molecules are an excellent organic semiconductor material, the intramolecular structure of the pentacene structure molecules is in herring skeleton arrangement, and the pentacene structure molecules have high carrier mobility. Compared with inorganic semiconductor materials, organic semiconductor materials have the advantages of low cost, integration with flexible substrates, good plasticity, simple manufacturing process and the like. In recent years, the acene type has been widely used in organic crystal Field Effect Transistors (FETs), and pentacene derivatives can expand the degree of conjugation of molecules, which is advantageous for delocalization of electrons.
Therefore, there is a need to develop a material combining metal organic frameworks of pentacene derivative structure, and it is expected to improve the conductivity of MOFs using the material.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a pentacene derivative metal organic framework material and application thereof.
To achieve the above objects, according to one aspect of the present invention, there is provided a pentacene derivative metal-organic framework material comprising a moiety in which a pentacene derivative ligand, which is a compound substituted with a tetra-aromatic ring at the 6,13-position of 6, 13-dimethylene-6, 13-dihydropentacene, is complexed with a metal atom.
Furthermore, the compound has four structural general formulas which are HUBU-1, HUBU-2, HUBU-3 and HUBU-4 respectively, and the specific structural formulas are as follows:
Figure SMS_1
wherein Ar1 is a benzene ring, a biphenyl ring, a acene ring, a heterocyclic ring or/and a benzo heterocyclic ring, ar2 is a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, an imidazole ring or/and an oxazole ring, X is a heteroatom, M is a metal atom, wherein the benzene ring is a para-substituted benzene ring, the biphenyl ring is 2, 6-disubstituted biphenyl, the acene ring is 4,4' -disubstituted biphenyl, the heterocyclic ring is 2, 5-disubstituted five-membered heterocyclic ring, the benzo heterocyclic ring is a benzo five-membered nitrogen-, oxygen-or/and sulfur-containing heterocyclic ring, the furan ring is 2-substituted furan, the thiophene ring is 2-substituted thiophene, the pyrrole ring is 2-substituted pyrrole, the pyridine ring is 2-substituted pyridine, the imidazole ring comprises 2-substituted imidazole and 4-substituted imidazole, the oxazole ring comprises 2-substituted oxazole and 4-substituted oxazole, and the heteroatom is a nonmetal atom capable of substituting a C atom in the structure.
Further, heteroatoms include one or more of oxygen, sulfur, nitrogen, and phosphorus. Preferably, the heteroatom is oxygen, sulfur or nitrogen.
Further, the metal atom is copper, zinc, nickel, cobalt, zirconium, manganese, iron, ruthenium, rhodium, palladium, platinum, gold, silver, titanium or/and aluminum. Preferably, the metal atoms are copper and zinc.
According to the second aspect of the invention, the application of the metal organic framework material of the pentacene derivative is also provided, and the metal organic framework material can be used as a sensitive material for fluorescence sensing, humidity sensing, chemical sensing and semiconductor gas sensing and is applied to the preparation of the above sensitive sensors. In fluorescence sensors it is used as a photo-responsive core material, in humidity sensors it is used as a water vapour responsive core material, in chemosensing it can be used as a chemical volatile adsorption responsive core material, in semiconductor sensors it can be used as an electrical signal responsive core material.
Generally, compared with the prior art, the above technical solution conceived by the present invention has the following beneficial effects:
in the material structure of the invention, a large pi-conjugated system is constructed due to the introduction of acene. The large pi conjugated system disperses the charge of the active intermediate generated in the sensing response process, and can effectively promote the stability of the pentacene derivative metal organic framework material; meanwhile, a large pi-conjugated system provides strong pi-pi intermolecular interaction, molecular assembly is promoted, structural order is maintained, two-dimensional planarity is constructed, charge carrier mobility and high conductivity of the material are improved, and the problem of poor conductivity of the metal organic framework material can be solved.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a tetra-p-benzoic acid substituted ligand at position 6,13 of 6, 13-dimethylene-6, 13-dihydropentacene provided in an example of the present invention.
FIG. 2 is a high resolution mass spectrum of the 6,13-tetra-p-benzoic acid substituted ligand of 6, 13-dimethylene-6, 13-dihydropentacene provided by the example of the present invention.
FIG. 3 is a powder X-ray diffraction of a tetra-p-benzoic acid substituted zinc metal organic framework material at 6,13-position of 6, 13-dimethylene-6, 13-dihydropentacene provided by an embodiment of the invention.
FIG. 4 is a scanning electron microscope image of a zinc metal organic framework material substituted with tetra-p-benzoic acid at the 6,13-position of 6, 13-dimethylene-6, 13-dihydropentacene provided by an example of the present invention.
Fig. 5 is a scanning electron microscope image at greater magnification of the zinc metal organic framework material of fig. 4.
FIG. 6 is a NMR spectrum of 6, 13-bis (dithienylmethylene) -6,13 dihydropentacene provided in the examples of the present invention.
FIG. 7 is a high resolution mass spectrum of a 6, 13-bis (dithienylmethylene) -6,13 dihydropentacene ligand provided by an example of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The invention provides a pentacene derivative metal organic framework material, which comprises a part formed by complexing a pentacene derivative ligand and a metal atom, wherein the pentacene derivative ligand is a compound substituted by a 6, 13-position tetra-aromatic ring of 6, 13-dimethylene-6, 13-dihydropentacene. Has four structural general formulas which are HUBU-1, HUBU-2, HUBU-3 and HUBU-4 respectively, and the specific structural formulas are as follows:
Figure SMS_2
wherein Ar1 is a benzene ring, a biphenyl ring, a acene ring, a heterocyclic ring or/and a benzo heterocyclic ring, ar2 is a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, an imidazole ring or/and an oxazole ring, X is a heteroatom, M is a metal atom, wherein the benzene ring is a para-substituted benzene ring, the biphenyl ring is 2, 6-disubstituted biphenyl, the acene ring is 4,4' -disubstituted biphenyl, the heterocyclic ring is 2, 5-disubstituted five-membered heterocyclic ring, the benzo heterocyclic ring is a benzo five-membered nitrogen-, oxygen-or/and sulfur-containing heterocyclic ring, the furan ring is 2-substituted furan, the thiophene ring is 2-substituted thiophene, the pyrrole ring is 2-substituted pyrrole, the pyridine ring is 2-substituted pyridine, the imidazole ring comprises 2-substituted imidazole and 4-substituted imidazole, the oxazole ring comprises 2-substituted oxazole and 4-substituted oxazole, and the heteroatom is a nonmetal atom capable of substituting a C atom in the structure. Heteroatoms include one or more of oxygen, sulfur, nitrogen, and phosphorus. Preferably, the heteroatom is oxygen, sulfur or nitrogen. The metal atoms are copper, zinc, nickel, cobalt, zirconium, manganese, iron, ruthenium, rhodium, palladium, platinum, gold, silver, titanium or/and aluminum. Preferably, the metal atoms are copper and zinc.
The metal organic framework material of the present invention has the following typical structural formulas:
Figure SMS_3
several exemplary methods for preparing the materials of the present invention are further illustrated below in conjunction with the examples.
EXAMPLE 1 preparation of Zinc Metal organic framework materials of pentacene derivatives
The preparation of 4,4' - (pentacene-6, 13-bipolylidene (methylene)) tetrabenzoic acid is carried out first, and then the zinc metal organic framework material of the pentacene derivative is synthesized.
(1) Synthesis of 6, 13-bis (dibromomethylene) -6,13 dihydropentacene (chemical structural formula is shown as I):
placing 4.3g of carbon tetrabromide and 6.8g of triphenylphosphine in a 250 ml round-bottom flask, adding 150 ml of anhydrous toluene, stirring the obtained mixed solution at normal temperature for 5 minutes, adding 1.0g of pentacenedione, and reacting at 80 ℃ for 12 hours under an inert atmosphere; after the reaction is finished, cooling to room temperature, filtering the mixed solution, evaporating the solvent under reduced pressure, performing column chromatography on the obtained crude product by using petroleum ether/dichloromethane (volume ratio of 4/1) as an eluent, and drying in vacuum to obtain 0.3g of white solid;
Figure SMS_4
(2) Synthesis of 4,4',4 ", 4'" - (pentacene-6, 13-bisylidene (methylideneidene)) tetraphenoate (chemical formula II):
0.31g of 6, 13-bis (dibromomethylene) -6, 13-dihydropentacene, 0.54g of p-methoxycarbonylphenylboronic acid, 0.42g of potassium carbonate and 60mg of tetrakis (triphenylphosphine) palladium were placed in a 100 ml round-bottom flask, 30 ml of degassed tetrahydrofuran aqueous solution (24 ml of THF,6 ml of water) was added, and the resulting mixture was frozen and degassed three times and heated under reflux for 24 hours under an inert atmosphere; after the reaction is finished, cooling to room temperature, extracting the reaction liquid for three times by using ethyl acetate, washing the combined organic layers for three times by using brine, drying the solution by using anhydrous sodium sulfate, filtering, evaporating the solvent under reduced pressure, performing column chromatography on the obtained crude product by using dichloromethane/ethyl acetate (the volume ratio is 9/1) as an eluent, and drying in vacuum to obtain 210mg of yellow solid.
Figure SMS_5
(3) Synthesis of 4,4',4 ", 4' - (pentacene-6, 13-bipolylidene (methylallylidene)) tetrabenzoic acid (chemical structure III):
110mg4,4' - (pentacene-6, 13-bipolylidene (methylene)) tetraphenyl ester (II) and 60mg sodium hydroxide were dissolved in 12 ml of a mixture of tetrahydrofuran, methanol and water (volume ratio: 1/1/1), and heated under reflux for 12 hours; after the reaction, the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure, 5 ml of water was added to the reaction flask, then 3M hydrochloric acid was added dropwise until the solution pH =2.0, and the yellow-green solid was obtained after suction filtration and drying.
Figure SMS_6
(4) The preparation method of the zinc metal organic framework material of the pentacene derivative comprises the following steps:
32mg of zinc nitrate hexahydrate is placed in a 10 ml high-pressure reaction tube, 2 ml of N, N-dimethylformamide is added, ultrasonic treatment is carried out until the solution is transparent, then 1 ml of distilled water is added, and 34mg4,4' - (pentacene-6, 13-bi-subunit (methylene) tetraphenic acid is added into the reaction tube, and the mixture is placed in an oven for reaction at 100 ℃ for 48 hours after ultrasonic treatment for 5 minutes; after the reaction is finished, cooling to room temperature, centrifuging, collecting solid, washing with DMF for three times, washing with methanol for three times, and drying in vacuum to obtain light yellow powder 20mg, namely the zinc metal organic framework material with the chemical structural formula of HUBU-1-Zn.
Figure SMS_7
Example 2
Synthesis of 6, 13-bis (dithiophenemethylene) -6,13 dihydropentacene
0.31g of 6, 13-bis (dibromomethylene) -6, 13-dihydropentacene, 1.2 g of tributyl (2-thienyl) tin, and 30 mg of tetrakis (triphenylphosphine) palladium were dissolved in 10 ml of DMF, and after three times of freezing and degassing, the mixture was reacted at 85 ℃ for 17 hours; after the reaction is finished, the solution is extracted for three times by ethyl acetate, the combined organic layers are respectively washed by water, 1M hydrochloric acid and saline, the solvent is evaporated under reduced pressure after drying, and the obtained crude product is subjected to column chromatography by using petroleum ether/dichloromethane (5/1) as an eluent to obtain 180mg of light yellow solid, namely the product of the following reaction formula.
Figure SMS_8
The pentacene derivative metal organic framework material can be used as a sensitive material for fluorescence sensing, humidity sensing, chemical sensing and semiconductor gas sensing, and is applied to preparation of various sensitive sensors.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a tetra-p-benzoic acid substituted ligand at the 6, 13-position of 6, 13-dimethylene-6, 13-dihydropentacene provided by the embodiment of the invention, and it can be known that the chemical shift value and the number ratio of hydrogen are consistent with the structure, and the total number of hydrogen is 32.
FIG. 2 is a high-resolution mass spectrum of a 6,13-tetra-p-benzoic acid substituted ligand of 6, 13-dimethylene-6, 13-dihydropentacene provided by the embodiment of the invention, and it can be known that the actually tested high-resolution mass spectrum (784.2109) is consistent with a theoretical value (784.2097), and the correctness of the material structure can be uniquely determined.
FIG. 3 is a powder X-ray diffraction of a zinc metal organic framework material substituted with tetra-p-benzoic acid at position 6, 13-position of 6, 13-dimethylene-6, 13-dihydropentacene provided in an example of the present invention, and it can be seen that the obtained metal organic framework material has good crystallinity, characteristic peak of diffraction angle 8-10 degrees, similar to benzene series zinc carboxylate metal framework material, showing characteristic peak of pi-pi interaction at about 25 degrees.
FIG. 4 is a scanning electron microscope image of a zinc metal organic framework material substituted by tetra-p-benzoic acid at 6, 13-position of 6, 13-dimethylene-6, 13-dihydropentacene provided by the embodiment of the invention, and the material has a two-dimensional layered morphology.
Fig. 5 is a scanning electron microscope image at greater magnification of the zinc metal organic framework material of fig. 4, from which it can be seen that the material exhibits a regular micro-morphology.
FIG. 6 is a NMR spectrum of 6, 13-bis (dithienylmethylene) -6,13 dihydropentacene provided in the example of the present invention, and it can be seen from the figure that chemical shift values and number ratios of hydrogen are consistent with the structure, and the total number of hydrogen is 24.
FIG. 7 is a high-resolution mass spectrum of the 6,13-bis (dithiophenemethylene) -6,13 dihydropentacene ligand provided by the embodiment of the invention, and the actually tested high-resolution mass spectrum (632.0761) is consistent with a theoretical value (632.0771), so that the correctness of the material structure can be uniquely determined.
It will be understood by those skilled in the art that the foregoing is only a preferred embodiment of the present invention, and is not intended to limit the invention, and that any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.

Claims (4)

1. A pentacene derivative metal organic framework material is characterized in that the pentacene derivative metal organic framework material is formed by complexing a pentacene derivative ligand and a metal atom, the pentacene derivative ligand is a compound substituted by a 6, 13-position tetra-aromatic ring of 6, 13-dimethylene-6, 13-dihydropentacene, and the pentacene derivative ligand has four types of structural general formulas which are HUBU-1, HUBU-2, HUBU-3 and HUBU-4 respectively, and the specific structural formulas are as follows:
Figure FDA0004058814040000011
wherein Ar1 is benzene ring, biphenyl ring, acene ring, heterocyclic ring or/and benzo heterocyclic ring,
ar2 is furan ring, thiophene ring, pyrrole ring, pyridine ring, imidazole ring or/and oxazole ring,
x is a hetero atom, M is a metal atom,
heteroatom means a non-metal atom which can replace C atom in the structure, the heteroatom comprises one or more of oxygen, sulfur, nitrogen and phosphorus, the metal atom is copper, zinc, nickel, cobalt, zirconium, manganese, iron, ruthenium, rhodium, palladium, platinum, gold, silver, titanium or/and aluminum,
wherein, the benzene ring refers to a para-substituted benzene ring,
the biphenyl ring is 2, 6-disubstituted biphenyl,
the acene ring refers to 4,4' -disubstituted biphenyl,
the heterocycle refers to a 2, 5-disubstituted five-membered heterocycle,
the benzo heterocycle refers to a benzo five-membered nitrogen-, oxygen-or/and sulfur-containing heterocycle,
the furan ring refers to a 2-substituted furan,
the thiophene ring refers to a 2-substituted thiophene,
the pyrrole ring refers to a 2-substituted pyrrole,
the pyridine ring refers to 2-substituted pyridine,
imidazole rings include 2-substituted imidazoles and 4-substituted imidazoles,
the oxazole ring includes 2-substituted oxazoles and 4-substituted oxazoles.
2. The metal-organic framework material of pentacene derivatives of claim 1, wherein the heteroatom is oxygen, sulfur or nitrogen.
3. A metal-organic framework material of pentacene derivatives according to claim 1 or 2, characterized in that the metal atoms are copper and zinc.
4. Use of the pentacene derivative metal organic framework material according to any one of claims 1 to 3 as a fluorescence, humidity, chemical, semiconductor gas sensing material.
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