CN117843978A - Two-dimensional supermolecule halogen bond organic framework XOFs, preparation method and application thereof - Google Patents

Two-dimensional supermolecule halogen bond organic framework XOFs, preparation method and application thereof Download PDF

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CN117843978A
CN117843978A CN202311783696.5A CN202311783696A CN117843978A CN 117843978 A CN117843978 A CN 117843978A CN 202311783696 A CN202311783696 A CN 202311783696A CN 117843978 A CN117843978 A CN 117843978A
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xofs
ligand
dimensional
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xof
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陈世贵
王璐
赵佳豪
夏宁
王纪科
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Wuhan University WHU
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl

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Abstract

The invention relates to the technical field of organic frame materials, in particular to a two-dimensional supermolecule halogen bond organic framework XOFs, a preparation method and application thereof, and the preparation method comprises the following steps: completely reacting the ligand with the iodine reagent in a solvent environment at a certain temperature, removing the solvent, washing the precipitate, and drying to obtain the product; the ligand is a ligand containing multidentate pyridine. The preparation method of the invention provides a novel method for synthesizing the XOFs, the crystallinity of the synthesized XOFs is enhanced by using an iodonium transfer exchange reaction and dynamic reversible ligand exchange, and the prepared XOFs have high crystallinity and structural stability, are used as a catalyst carrier, show excellent catalytic activity in Heck coupling reaction, and have high yield and recoverability.

Description

Two-dimensional supermolecule halogen bond organic framework XOFs, preparation method and application thereof
Technical Field
The invention relates to the technical field of organic frame materials, in particular to a two-dimensional supermolecule halogen bond organic framework XOFs, a preparation method and application thereof.
Background
In recent years, organic framework materials, such as Metal Organic Frameworks (MOFs), covalent Organic Frameworks (COFs), hydrogen bond organic frameworks (HOFs) and Supramolecular Organic Frameworks (SOFs), have attracted attention in the fields of gas storage, separation, electronics and catalytic applications. These frames have an adjustable porous structure and rich functionality, which is achieved by different connection nodes. The connection nodes play a key role in determining the nature and function of the organic frameworks, and therefore the development of new materials based on different connection methods is of great importance. The method not only can expand the structural diversity and functional diversity of the organic framework, but also can design materials suitable for specific applications. Therefore, the development of novel organic framework materials based on different connection methods is still a key research field, and has great potential for advancing material science and engineering.
Among them, the three-center-four-electron [ N-x+ -N ] halogen bond is a powerful tool for constructing complex supramolecular aggregates with excellent stability and structure-directing ability due to its high bond energy and bonding pattern. Such halogen bonds have been successfully used in the manufacture of various supramolecular assemblies including molecular cages, molecular capsules, molecular helices, molecular motors and supramolecular chiral polymers. Recently, researchers have successfully constructed a new type of two-dimensional (2D) supramolecular halogen-bonded organic frameworks (XOFs) using [ N-i+ -N ] halogen bonds. These XOFs exhibit unique properties in terms of fatty acid vapor adsorption, iodination, and the like. Due to their high stability and good structural integrity, these XOFs are considered potential materials for use in a variety of applications.
Organic frameworks based on [ N-i+ -N ] halogen bonds represent a significant advance in the field of supramolecular chemistry and offer exciting opportunities for developing new materials with tailored properties and functions. By precisely controlling the connection nodes and adjusting the chemical structure, researchers can design and build organic framework materials with specific properties and functions. These novel materials are expected to play an important role in applications in gas storage, separation, catalysis and other fields.
Traditional XOFs preparation methods involve coordination of a pyridyl unit to an ag+ ion to form an N-ag+ -N structure, followed by in situ substitution of the ag+ ion with an i+ ion upon addition of iodine to produce an N-i+ -N linker. However, in this process, the insoluble AgI by-product produced is difficult to completely remove due to its low solubility. This problem may adversely affect the crystallinity, performance and function of XOFs, and thus solving this problem is a critical and urgent task.
Disclosure of Invention
It is an object of the present invention to provide a method for preparing two-dimensional supramolecular halo-bonded organic frameworks (XOFs) having enhanced crystallinity by utilizing iodonium transfer exchange reaction and dynamic reversible ligand exchange. The method aims to solve the problems of AgI byproducts and low crystallinity in the traditional preparation process of the XOFs.
The second purpose of the invention is to provide a two-dimensional supermolecule halogen bond organic framework XOFs which has high crystallinity and good stability.
The invention further aims to provide an application of the two-dimensional supermolecule halogen bond organic frameworks XOFs.
The scheme adopted by the invention for achieving one of the purposes is as follows: a preparation method of two-dimensional supermolecule halogen bond organic frameworks XOFs comprises the following steps: completely reacting the ligand with the iodine reagent in a solvent environment at a certain temperature, removing the solvent, washing the precipitate, and drying to obtain the product;
the ligand is a ligand containing multidentate pyridine.
Preferably, the ligand is at least one of the following structures:
preferably, the solvent is at least one of methanol, ethanol, dichloromethane, chloroform, and tetrahydrofuran.
Preferably, the molar ratio of the ligand to the iodinated agent is between 1 and 4.
Preferably, the temperature of the reaction is from room temperature to 100 ℃.
Preferably, the reaction time is from 1 to 36 hours.
The scheme adopted by the invention for achieving the second purpose is as follows: the two-dimensional supermolecule halogen bond organic frameworks XOFs prepared by the preparation method of the two-dimensional supermolecule halogen bond organic frameworks XOFs have any one of the structures shown in the following formula:
the scheme adopted by the invention for achieving the third purpose is as follows: the application of the two-dimensional supermolecule halogen bond organic frameworks XOFs is used as a catalyst carrier.
The invention has the following advantages and beneficial effects:
the preparation method of the invention provides a novel method for synthesizing the XOFs, and the crystallinity of the synthesized XOFs is enhanced by using an iodonium transfer exchange reaction and dynamic reversible ligand exchange.
The preparation method provided by the invention avoids the problems of AgI byproducts and low crystallinity in the traditional preparation process, thereby obtaining the XOFs material with high purity, complete structure and excellent performance.
The preparation method provided by the invention adopts ligand exchange strategy to provide error correction or reconstruction for the construction of the XOFs, provides potential for improving the crystallinity of the XOFs by introducing dynamic reversible chemistry, provides a new way for the construction of the XOFs, and greatly expands the convenient preparation and diversified application range of the XOFs.
The XOFs prepared by the preparation method provided by the invention have high crystallinity and structural stability.
The XOFs prepared by the preparation method provided by the invention are used as a catalyst carrier, have excellent catalytic activity in Heck coupling reaction, and have high yield and recoverability.
Drawings
FIG. 1 is a prior art process (a) for preparing XOFs by cationic substitution and a ligand exchange reaction process (b) herein;
FIG. 2 is a conceptual diagram of amorphous and crystalline XOF-TPT produced by cation substitution and ligand exchange reactions;
FIG. 3 is a photograph of BPy in MeOH (1.0 mM) after addition of various equivalents of Py-I in example 1;
FIG. 4 is a graph of yield data for the precipitate formed in example 1 by adding various equivalents of Py-I to BPy in MeOH (1.0 mM);
FIG. 5 is an X-ray photoelectron spectrum of the product prepared in example 3 and comparative example 1;
FIG. 6 is a sample of XOF-TPT prepared in example 3 E Is a PXRD diagram of (1);
FIG. 7 is a schematic diagram of XOF-BPy prepared in example 3 E 、XOF-TPT E 、XOF-TPPA E (FT-IR) infrared spectrogram of (C);
FIG. 8 shows a Pd@XOF-TPT prepared in the application example E The recycling recovery rate of the catalyst.
Detailed Description
For a better understanding of the present invention, the following examples are further illustrative of the present invention, but the contents of the present invention are not limited to the following examples only.
Example 1
Preparation of 1D XOF BPyE:
4,4' -bipyridine (BPy) was reacted with an appropriate amount of Py-I (Barlenga iodine positive reagent) in methanol solution.
Ligand exchange reaction: 1 equivalent of BPy monomer and different equivalents of Py-I (0.1, 0.2, 0.3, 0.5, 0.8, 1.0, 2.0 and 5.0 respectively) are added into methanol solution simultaneously to carry out ligand exchange reaction at room temperature, and the reaction is carried out within 24 hours. The results are shown in FIGS. 3 and 4, and according to the experimental results, the yield of XOF-BPy gradually increases as the amount of Py-I added increases. When more than 2.0 equivalents of Py-I were added, the yield of insoluble polymer XOFs, as determined by weighing, reached about 70%.
Example 2
Selecting a target compound and a model compound: 2,4, 6-tris (4-pyridyl) -1,3, 5-triazine (TPT) was chosen as the target compound due to its wide application of rigid planar structures in two-dimensional materials. TPT has a rigid structure and is suitable for preparing 2D XOF.
Synthesis of 2,4, 6-tris (pyridin-4-yl) -1,3, 5-triazine (TPT):
18-crown-6 (1.00 g, 3.80 mmol) and KOH (0.23 g, 4.00 mmol) were dissolved in 5ml EtOH with stirring for 10 min. The solution was concentrated to remove EtOH. To this oil was added 4-cyanopyridine (10.00 g,96.00 mmol). The mixture was transferred to a 25mL stainless steel reactor lined with polytetrafluoroethylene and heated at 200 ℃ for 7 hours. After cooling to room temperature, the brown solid was washed three times with 50mL of hot pyridine to give a white solid. The white solid was dissolved in 50mL of dilute HCl, reprecipitated with aqueous NH3, filtered, washed at least three times with 50mL portions of CH3CN, and then dried overnight in a vacuum oven at 80 ℃ to give 2.50g.
Example 3
A solution of Py-I (0.08-0.32 mmol) in methanol (2-5 mL) was added drop wise to BPy, TPT, TPPA (tris (4- (pyridin-4-yl) phenyl) amine), TPPE (1, 2-tetrakis (4- (pyridin-4-yl) phenyl) ethylene) (0.08-0.3, respectivelyIn a solution of 2 mmol) in methanol (1-3 mL) a precipitate immediately resulted. After ultrasonic dispersion, the solution is heated at 25-80℃for 1-38 hours. The XOF-TPTE was isolated by filtration and washed repeatedly with CH2Cl2 and MeOH. The precipitate was dried under high vacuum overnight. The products were designated as XOF-BPy, respectively E 、XOF-TPT E 、XOF-TPPA E ,XOF-TPPE E。
The molecular structural formula of each product is shown as follows:
XOF-BPy E ：
XOF-TPT E ：XOF-TPPA E ：XOF-TPPE E ：
comparative example 1
Traditional cationic substitution methods produce XOF:
AgBF 4 A solution of (0.24-0.48 mmol) in methanol (1-5 mL) was added drop-wise to a solution of BPy, TPT, TPPA, TPPE (0.08-0.32 mmol) in MeOH (1-3 mL), respectively. After stirring the solution at room temperature for 1 hour, a solution of iodine (0.08-0.32 mmol) in MeOH (1-5 mL) was added. The solution was then degassed three cycles with freeze pump thawing and the mixture heated at 120 ℃ for 3 hours. Then, the solvent was removed under reduced pressure without heating. The precipitate was dried under vacuum overnight. Respectively obtaining the product XOF-BPy S 、XOF-TPT S 、XOF-TPPA S ,XOF-TPPE S 。
FIG. 1 is a prior art step (a) of preparing XOFs by cationic substitution and a method (b) of preparing XOFs by ligand exchange reaction in the present application. FIG. 2 is a conceptual diagram of amorphous and crystalline XOF-TPT produced by cation substitution and ligand exchange reactions.
X-ray photoelectron spectra of the products prepared in example 3 and comparative example 1 are shown in FIG. 5, from which it can be seen that:
XOF-BPy E x-ray photoelectron spectroscopy (XPS) analysis of the surface chemistry of (C) shows that, with XOF-BPy S In contrast, at 620.9eV (I3 d 5/2 ) And 632.4eV (I3 d 3/2 ) Only one pair of peaks is attributed to I + 。
XOF-TPT S Two sets of signal peaks are shown by XPS spectra of (c): 620.4eV (I3 d) 5/2 ) And 631.9eV (I3 d 3/2 ) The peak at is assigned to I + Other peaks were assigned to the AgI species. As expected, XOF-TPT E Is measured at 632.4eV (I3 d 5/2 ) And 633.0eV (I3 d 3/2 ) Only one pair is shown due to I + 。
XOF-TPPA E Is only 619.4eV (I3 d) 5/2 ) And 630.9eV (I3 d 3/2 ) The peak is shown here due to I + Without any AgI peaks.
Preparation of XOF-TPT in example 3 as shown in FIG. 6 E From the figure it can be seen that the experimental PXRD pattern reveals reflections (100), (010), (020), (200), (300), (400), (231) and (33) at 4.52 °, 4.21 °, 8.68 °, 9.13 °, 12.91 °, 17.16 °, 24.64 ° and 25.63 ° (2θ), respectively, illustrating the XOF-TPT prepared E Has good crystallinity.
As shown in FIG. 7, XOF-BPy prepared in example 3 E 、XOF-TPT E 、XOF-TPPA E (FT-IR) infrared spectrogram of (C), as can be seen from the figure: compared with BPy, XOF-BPy E Is 18cm -1 This is mainly due to the increase in force constant caused by the decrease in charge density of the pyridine ring during coordination with iodine (I). 1040cm -1 The broad peak at this point is due to the asymmetric stretching mode of BF 4-. Compared with free TPPA, XOF-TPPA E The IR spectrum of (C) shows a significant blue shift of the c=n peak. XOF-TPT E Is shown by the infrared spectrum of (A), compared with free TPT, xOF-TPT E The tensile vibration peak of c=n on C has significantly shifted blue, indicating that TPT was successful with I + Coordination to form the target product.
Application example 1
Preparation of a recyclable organopalladium-metal heterogeneous catalyst Pd@XOF-TPT: palladium acetate was loaded on to XOF-TPT prepared in example 3 E In the above, a recyclable Pd@XOF-TPT is prepared E A catalyst.
Pd (OAc) 2 Dissolving in dichloromethane, and adding XOF-TPT E . The mixture was kept stirring at room temperature for 24 hours. The solid obtained by centrifugation was separated by CH 2 Cl 2 Repeatedly washing in CH 2 Cl 2 Soaking for 12 hours. After filtration, vacuum drying at 60℃for 12 hours, pd@XOF-TPT is obtained E Pale yellow powder.
Catalytic reaction evaluation: the Heck coupling reaction is taken as a model reaction, and Pd@XOF-TPT is used under the optimal condition E The reaction of the catalyst in dioxane was continued for 3 days. According to the experimental results, the product methyl cinnamate was provided in 98% yield.
Range study: under the optimum reaction conditions, a range of different aryl halides and substituted olefins was investigated. The results show that most aryl olefins and olefins can be efficiently converted to coupled products in yields as high as 98%.
Optimization of reaction conditions: iodobenzene (20.00 mg,1.00 mmol), methyl acrylate (10.30 mg,1.20 mmol), triethylamine (20.30 mg,2.00 mmolppd@xof-TPT) E To an anhydrous solvent (toluene/dioxane/N, N-dimethylformamide/N, N-dimethylacetamide 4 mL) was added (7.50 mg,2 mol%). The reaction mixture was stirred at 100 ℃ under reflux under an argon atmosphere. After the reaction was completed (monitored by TLC), the mixture was filtered and the solid was washed with dichloromethane. The filtrate was then evaporated under reduced pressure. The crude product was then dissolved in ethyl acetate and filtered to remove excess TBAB. After filtration, the solvent was evaporated under reduced pressure. The mixture was purified by column chromatography.
Application example 2
Aryl halide (1.00 mmol), olefin (1.20 mmol), triethylamine (TEA) (2.00 mmolppd@XOF-TPT) E (7.50 mg,2 mol%) was added to dioxane (4 mL). The reaction mixture was heated to 100deg.CReflux stirring under argon atmosphere. After the reaction was completed (monitored by TLC), the mixture was filtered and the solid was washed with dichloromethane. The filtrate was then evaporated under reduced pressure. The crude product was then dissolved in ethyl acetate and filtered to remove excess TBAB. After filtration, the solvent was evaporated under reduced pressure. The mixture was purified by column chromatography.
Recyclability assessment: pd@XOF-TPT E Can be removed and recovered from the reaction medium by simple filtration. After multiple recovery experiments, pd@XOF-TPT E Still maintaining high stability and catalytic activity. As shown in FIG. 8, the catalytic efficiency of the supported catalyst prepared in this application example after multiple recovery can be seen from the graph that Pd@XOF-TPT of the invention E The catalyst still has higher recovery rate after being recovered for a plurality of times.
While the invention has been described with respect to the preferred embodiments, it will be understood that the invention is not limited thereto, but is capable of modification and variation without departing from the spirit of the invention, as will be apparent to those skilled in the art.

Claims (8)

1. The preparation method of the two-dimensional supermolecule halogen bond organic frameworks XOFs is characterized by comprising the following steps of: completely reacting the ligand with the iodine reagent in a solvent environment at a certain temperature, removing the solvent, washing the precipitate, and drying to obtain the product;
the ligand is a ligand containing multidentate pyridine.
2. The method for preparing the two-dimensional supermolecule halogen bond organic frameworks XOFs according to claim 1, which is characterized by comprising the following steps:
the ligand is at least one of the following structures:
3. the method for preparing the two-dimensional supermolecule halogen bond organic frameworks XOFs according to claim 1, which is characterized by comprising the following steps: the solvent is at least one of methanol, ethanol, dichloromethane, chloroform and tetrahydrofuran.
4. The method for preparing the two-dimensional supermolecule halogen bond organic frameworks XOFs according to claim 1, which is characterized by comprising the following steps: the molar ratio of the ligand to the iodine reagent is 1-4.
5. The method for preparing the two-dimensional supermolecule halogen bond organic frameworks XOFs according to claim 1, which is characterized by comprising the following steps: the temperature of the reaction is from room temperature to 100 ℃.
6. The method for preparing the two-dimensional supermolecule halogen bond organic frameworks XOFs according to claim 1, which is characterized by comprising the following steps: the reaction time is 1-36h.
7. A two-dimensional supramolecular halo-bond organic frameworks XOFs prepared by the method for preparing the two-dimensional supramolecular halo-bond organic frameworks XOFs according to any one of claims 1-6, characterized in that the structure is any one of the following formulas:
8. use of two-dimensional supramolecular halo-bonded organic frameworks XOFs according to claim 7, characterized in that: for use as a catalyst support.
CN202311783696.5A 2023-12-21 2023-12-21 Two-dimensional supermolecule halogen bond organic framework XOFs, preparation method and application thereof Pending CN117843978A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118063789A (en) * 2024-04-24 2024-05-24 山东理工大学 Porous double condensed ring ligand coordination polymer material, preparation method thereof and application of porous double condensed ring ligand coordination polymer material in separation of toluene/methylcyclohexane

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118063789A (en) * 2024-04-24 2024-05-24 山东理工大学 Porous double condensed ring ligand coordination polymer material, preparation method thereof and application of porous double condensed ring ligand coordination polymer material in separation of toluene/methylcyclohexane

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