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WO2009098001A1 - Composés organométalliques à base de triptycène - Google Patents

Composés organométalliques à base de triptycène Download PDF

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Publication number
WO2009098001A1
WO2009098001A1 PCT/EP2009/000601 EP2009000601W WO2009098001A1 WO 2009098001 A1 WO2009098001 A1 WO 2009098001A1 EP 2009000601 W EP2009000601 W EP 2009000601W WO 2009098001 A1 WO2009098001 A1 WO 2009098001A1
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WO
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Prior art keywords
tdc
ligand
mof
compound according
triptycene
Prior art date
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Ceased
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PCT/EP2009/000601
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German (de)
English (en)
Inventor
Stefan BAHNMÜLLER
Gerhard Langstein
Julia Hitzbleck
Bernhard Rieger
Anna Katharina Ott
Sergei Vagin
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Covestro Deutschland AG
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Bayer MaterialScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/49—Polycyclic acids containing rings other than six-membered aromatic rings

Definitions

  • the invention relates to crystalline organometallic skeleton compounds which are based on an organic ligand having a triptycene skeleton and preferably form two-dimensional layer systems, and a process for their preparation.
  • Crystalline organometallic framework compounds are known in the art and can be selectively prepared by a variety of synthetic routes.
  • Current research activities are focused on the isolation of porous metal organic frameworks (MOFs), the reversible storage and separation of gases and volatiles, as well as for applications in catalysis.
  • MOFs porous metal organic frameworks
  • Organometallic frameworks themselves have been known since the 1960's as a promising class of inorganic-organic hybrid materials.
  • the molecular architectures which can be adjusted in a targeted manner, and which also allow a rational design of two- and three-dimensional lattice structures with variable cavities, complement the group of porous inorganic materials.
  • MOFs metal-organic frameworks
  • organometallic coordination polymers organometallic coordination polymers
  • MOF-5 forms a simple and temperature-stable cubic framework consisting of (Zn 4 O) zinc carboxylate coordination units
  • IR-MOFs isoreticular metal-organic frameworks
  • 2D and SD framework compounds that are based on M 3 , M 2, or M 3 O metal (oxide) units linked by at least bidentate organic bridging ligands
  • Compounds are preferably di-, tri- or tetracarboxylic acids which can be derived in the simplest case of terephthalic acid.
  • Annulated aromatic systems with carboxylic acid functions are preferably used to achieve larger pores for gas storage.
  • the prior art bridging ligands and resulting organometallic frameworks are listed, for example, in WO 2007/090864 A1. These compounds extend the group of microporous materials and have produced a steadily increasing number of MOF structures in recent years.
  • Triptycene derivative-based metal-organic framework compounds have hitherto been described only as transition metal complexes with chromium tricarbonyl or silver perchlorate and triptycene and have a coordinative bond to the aromatic system of the ligand to form porous networks (S. Toyota, H. Okuhara, M. Oki, Organometallics 16 Muniquata, Wu, K. Sugimoto, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, N. Maeno, M. Fujita, Inorganic Chemistry 38 (1999), 5674- (1997), 4012-4015; 5680).
  • Two-dimensional porous networks of CuI and triptycenylquinoxalines have a high thermal stability and are suitable for the reversible absorption of solvent molecules or organic compounds from aqueous solution (J.H. Chong, MJ MacLachlan, Inorganic Chemistry 45 (2006), 1442-1444).
  • Organometallic framework compounds with 1,4-dicarboxylic acid bicyclo [2.2.2] octane as the coordinating ligand which is a simplified structure of the triptycene skeleton, has been described by Li and coworkers (Li, J., Lee, T. Lee, DH Olson, W. Bi, T. Emge, J. Li, Abstracts, 39th Middle Atlantic ACS Regional Meeting, Collegeville, PA, United States, May 16-18 (2007), MARM-008).
  • the suitability of triptycene-1, 4-dicarboxylic acid compounds for the preparation of organometallic framework compounds and other structures with a comparable backbone are not known in the prior art.
  • Organometallic framework compounds which have an ionic bond to a triptycene ligand have not been described to date.
  • the object of the invention is to provide novel organometallic framework compounds for applications such as reversible storage of gases and liquids, in catalysis and materials with new functional properties.
  • a particular object of the invention is the preparation of novel organometallic frameworks with two-dimensional rigid layers based on Triptycenderivaten. Variable slice spacings can be adjusted by a suitable choice of spacer ligands.
  • the invention relates to organometallic framework compounds based on at least one metal cation and at least one bridging bidentate ligand and additionally a further mono- or bidentate spacer ligand, characterized in that the bidentate bridging ligand is formed on a triptycene skeleton of the formula (I)
  • R 1 to R 2 are independently hydrogen, Ci - to Cn alkyl, Ci - Cn alkoxy, Ce to C 2 - cycloalkyl, C 6 - to C 2 - aryl, or halogen, preferably hydrogen and / or in which each two adjacent radicals R 2 and R 3 , R 6 and R 7 and Ri 0 and R n independently of one another in each case together form part of a monocyclic or cyclic condensed ring system which is aromatic or non-aromatic and optionally one or more Heteroatoms from the series: contains oxygen, sulfur, nitrogen and phosphorus,
  • R 20 and R 21 independently of one another are a radical -YR 22 , wherein Y is a Ci - is 2 to C arylene group and R 22 is a radical from the series comprising -OH, -COOH, -NH 2, -COSH and -CSSH, preferably - to C 6 -alkylene radical or a C 6 - COOH stands.
  • organometallic framework compounds described here can be prepared by analogous methods known in principle from the prior art, such as solvothermal synthesis, by use of microwave radiation or by diffusion-controlled synthesis at room temperature from the compounds of formula (1), metal salts and spacer ligands. in the
  • starting materials are used: a metal compound, an organic bridging coordinating ligand (I) and a spacer ligand (IT), which are combined in a solvent and described in more detail below.
  • I organic bridging coordinating ligand
  • IT spacer ligand
  • a triptycender derivative with modifications to the bridgehead of the bicyclo [2.2.2] octane skeleton is particularly advantageously used, since this produces organometallic framework compounds with a threefold ligand, which are part of this invention.
  • organometallic framework compounds with a threefold ligand which are part of this invention.
  • two-dimensional layer structures with ⁇ (metal) 2 (ligand) 4 ⁇ coordination units and no interpenetrating networks are preferably formed.
  • the solvent molecules or spacer ligands which dative link these triptycene coordination polymer layers can be easily exchanged, thus making the metal centers readily accessible for catalytic processes.
  • the metal compound to be used for the preparation of the novel organometallic skeleton compounds is in particular a metal salt of a metal which is selected from a
  • Metal salt is preferably a halide, nitrate, sulfate, carboxylate, hydroxide, oxide or alkoxide, and optionally also used as the corresponding hydrate. As particularly preferred
  • Metals for the metal cation are selected from zinc, cadmium, copper, iron, chromium, cobalt, nickel, palladium, platinum, ruthenium, rhenium, yttrium, lanthanum, terbium and boron or aluminum. Particularly preferred are zinc, cadmium, cobalt and copper, which in the new
  • Framework compound present as divalent cations.
  • the organic coordinating ligand (I) is based on a triptycene skeleton and is characterized by two functional coordination units R 22 .
  • the synthesis of the triptycene skeleton is carried out, for example, by a process which is similar to the prior art (US Pat. No. 6,962,758 B2).
  • Various substitution patterns of the backbone can be achieved by using corresponding anthracene and Anthranilkladerivaten according to methods known in the art (FR 1,520,625).
  • R 22 is preferably a functional group which can form a coordinative bond to the metal cation, particularly preferably -OH, COOH, -NH 2 , -COSH, -CSSH, most preferably -COOH.
  • the functional group R 22 can either be attached directly to the triptycene skeleton or via a Q- to C 6 -
  • Alkylene or a C 6 - to Ci 2 -Arylenoli be connected to the triptycene skeleton.
  • the triptycene skeleton may be substituted as described above with residues of Ri to Ri 2 , wherein Ri to Ri 2 are the same or different and are preferably selected from the series
  • radicals Ri to Ri 2 can also be part of a mono- or polycyclic system which is optionally aromatic and in particular also heteroatoms, for example oxygen,
  • Sulfur, nitrogen, and phosphorus may contain. Particularly preferred are the adjacent residues form R a part of a ring system as described above 2 and R 3, R 6 and R 7, and Rio and Rn, in particular an aromatic ring system. Examples of possible
  • spacer ligands (II) provides structurally stable organometallic frameworks in the form of two-dimensional ⁇ (metal) 2 (ligand (I)) 4 ⁇ layers, which are separated by the spacer ligands (H).
  • the spacer ligand may be monodentate and be selected in particular from the series of alkylformamides (dimethylformamide, diethylformamide,
  • Dibutylformamide as well as dimethylsulfoxide, N-methylpyrrolidone, or bidentate and in particular be selected from the series of substituted phenazines, pyrazines, 4,4-bipyridines and para-phenylenevinylenes, in particular 1,4-diazabicyclo [2,2 , 2] octane, 4,4-bipyridine, 4,4-
  • Methanol, ethanol, alkylformamide (dimethylformamide, diethylformamide), acetonitrile, chlorobenzene, dimethyl sulfoxide, N-methylpyrrolidone or a mixture of two or more of these solvents is preferably used as a suitable solvent for the preparation of the novel organometallic framework compounds.
  • the organometallic framework compounds formed in the above-described processes can be separated by removal of the solvent.
  • the guest molecules (water or solvent) contained in the cavities of the organometallic skeleton compounds can be removed at elevated temperature and preferably reduced pressure, thereby giving compounds of precisely defined composition.
  • the preparation of the organometallic framework compounds according to the invention is generally carried out as follows:
  • a metal salt and one or more of the abovementioned ligands (I) and spacer ligands (II) are selected in a solvent from the series: methanol, ethanol, alkylformamide (dimethylformamide, diethylformamide), acetonitrile, chlorobenzene, dimethylsulfoxide, N-methylpyrrolidone, preferably dimethylformamide or diethylformamide, or a mixture of two or more of these solvents, and then dissolved at a temperature of 20 0 C to 160 0 C, preferably at a temperature of 80 0 C to 120 0 C for a period of 9 to 120 hours of crystallization subjected and then isolated.
  • Another method of synthesis is the use of microwave radiation.
  • reaction components are dissolved in one or more of the solvents described above and for up to 10 minutes, preferred are reaction times of 1 to 3 minutes, at 70 0 C to 120 0 C, preferably 80 0 C to 100 0 C, in a microwave Radiation power of 100 to 200 watts and a frequency of 2.45 GHz reacted.
  • organometallic framework compounds can also be carried out at room temperature with diffusion-controlled addition of the spacer ligands (II) or reaction accelerators (for example base). In this case, the linker and the metal salt are dissolved and the reaction is started by diffusion of a third component into the reaction mixture.
  • Organometallic framework compounds of the invention Possible applications of the organometallic framework compounds of the invention are the reversible storage and separation of gases and other volatile substances such as odors, as a stationary phase in chromatographic separation processes and as sensors, especially as redox and catalyst materials in the heterogeneous catalytic conversion of gas mixtures or substances in Solutions.
  • Organometallic framework compounds show the advantage over other porous materials such as zeolites of the more flexible, rational construction of the networks and the simple targeted modification of the resulting pore and layer structures. The uses mentioned are a further subject of the invention.
  • organometallic framework compounds of the invention described herein provide a stable structure within the ⁇ (metal) 2 (ligand (I)) 4 ⁇ layers and readily available coordination sites at the metal center between the layers through reversible exchange of spacer ligands (JJ).
  • JJ spacer ligands
  • Two-dimensional layer systems such as TDC-MOF-X in which the third dimension layers are bridged by a spacer ligand such as bipyridine exhibit reversible uptake of low molecular weight (polar) substances.
  • the scaffold structure can change by widening the distance between the two-dimensional layers without destroying the organometallic framework compound.
  • H 2 -TDC 9,10-Triptycenedicarboxylic acid
  • H 2 -TDC 9,10-Triptycenedicarboxylic acid
  • TDC-MOF-I no weight loss from 30 to 270 0 C,> 500 ° C (TDC).
  • Figure 1 shows the structure of a TDC-MOF-I assembly in a schematic representation.
  • TDC-MOF-3 Calculated for [Zn 2 (C 22 H 12 O 4 ) 2 (DMF) 2 (DMF)]: C 61.76; H 4.40; N 4.08%. Found: C 61.57; H 4.57; N 4.19% TGA (TDC-MOF-3): Weight loss: 140-175 0 C (-6.6%, DMF);. 240-500 0 C (-17.0%, ⁇ 2xDMF), 520-630 0 C (-32.9%)
  • Figure 2 shows the layer structure of TDC MOF-3 in a schematic representation
  • TDC-MOF-4 Calculated for [Zn2 (C22H12O4) 2 (BiPy)]: C 67.03; H 3.33; N 2.90%. Found: C 66.64; H 3.48; N 2.97%.
  • Figure 3 shows the framework structure of the TDC-MOF-4 in a schematic representation.
  • MOF-5) Calculated for [Zn 2 (C 22 H 12 O 4 ) 2 (BiPyTz)]: C 64.20; H 3.08; N 8.02%. Found: C 63.81;
  • Single-crystal X-ray diffraction analyzes (CU K Q or M ⁇ ⁇ at 100-150 K) and powder X-ray analyzes (Cu K ⁇ at RT) show that all TDC MOFs are built from 2-D layers of typical paddle wheel Zn 2 clusters (see Figures 1 and 2) ). Due to the interactions of triptycene units within a layer, the layers are particularly strongly stabilized and joined together by a spacer linker. Bidentate spacer linkers connect the layers relatively tightly together by the axial coordination of the zinc clusters, while monodentate axial ligands hold the layers together only with pure van der Waals interactions. Therefore, the layer spacing can be modulated, for example, by the guest exchange or the guest removal.
  • TDC MOFs The dense arrangement of triptycene units in a 2-D layer does not allow framework interpenetration in TDC MOFs.
  • the crystal structure data of TDC MOFs are summarized in Table 1. Table 1. Crystal structure data of triptycendicarboxylic acid MOFs
  • TDC-MOF-I and -3 occupy a very low permanent porosity confirmed by adsorption of argon.
  • the chloroform-washed and vacuum-dried TDC-MOF-4 samples show the argon type I adsorption isotherms as an adsorbate, typical of solids with open micropores.
  • FIG. 4 PXRD spectrum of TDC-MOF-7 unloaded (batch 5), evacuated (batch 5), and resolvated (batch 5).
  • a sample (5-50 mg) of a TDC-MOF-4 prepared by the methods described above was vacuum dried at 100 ° C. for 48 h. Subsequently, the sample was exposed to a saturated vapor atmosphere of a volatile compound such as water, amines, diacetyl or isoamyl acetate. In the case of water and amines, decomposition of the MOF is observed. In the case of diacetyl, the previously beige MOF assumes both the color of the diacetyl and the characteristic odor. When loading the MOFs with isoamyl acetate is the clearly perceive characteristic odor. Analytical data compare: Figures 5-7.
  • Figure 5 represents the XRPD spectra of the TDC MOF-4; Herein, the numbers 1 to 5: 1 - TDC MOF-4, 2 - after emptying, 3, - after offset with DEF and 4.5 - after evaporation with diacetyl or isoamyl acetate.
  • Figure 6 shows IR spectra of the absorption of diacetyl in TDC-MOF-4: dashed line - empty TDC-MOF-4, solid line - TDC-MOF-4 after absorption of diacetyl.
  • FIG. 7 IR spectra of the absorption of isoamyl acetate in TDC-MOF-4: dashed line - empty TDC-MOF-4, solid line - TDC-MOF-4 after absorption of isoamyl acetate.
  • Figure 5 PXRD spectrum of MOF-4 line 2 (unloaded), 5 (loaded with isoamyl acetate), 4 (loaded with diacetyl).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne des composés organométalliques à base de dérivés de triptycène, notamment de 9,10-dicarboxylate de triptycène, ainsi qu'un procédé permettant de les produire.
PCT/EP2009/000601 2008-02-05 2009-01-30 Composés organométalliques à base de triptycène Ceased WO2009098001A1 (fr)

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JP2011093894A (ja) * 2009-09-30 2011-05-12 Kuraray Co Ltd 金属錯体及びそれからなる分離材
WO2011105521A1 (fr) * 2010-02-24 2011-09-01 株式会社クラレ Complexe métallique, et adsorbant, matériau d'occlusion et matériau séparateur obtenus à partir de ce complexe
CN110628037A (zh) * 2019-09-12 2019-12-31 重庆师范大学 黄色荧光的混配体锰超分子聚合物及其制备方法与应用
WO2020230756A1 (fr) 2019-05-13 2020-11-19 学校法人立教学院 Corps structural organométallique
CN115850161A (zh) * 2022-11-26 2023-03-28 郑州大学 基于三蝶烯配位自组装四面体超分子笼、制备方法及应用
CN119591816A (zh) * 2024-12-06 2025-03-11 华侨大学 一种三蝶烯改性β-酮烯胺共价有机框架、其制备方法及其用途

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011093894A (ja) * 2009-09-30 2011-05-12 Kuraray Co Ltd 金属錯体及びそれからなる分離材
WO2011105521A1 (fr) * 2010-02-24 2011-09-01 株式会社クラレ Complexe métallique, et adsorbant, matériau d'occlusion et matériau séparateur obtenus à partir de ce complexe
CN102762536A (zh) * 2010-02-24 2012-10-31 可乐丽股份有限公司 金属络合物以及由其制成的吸附材料、吸留材料和分离材料
JPWO2011105521A1 (ja) * 2010-02-24 2013-06-20 株式会社クラレ 金属錯体、並びにそれからなる吸着材、吸蔵材及び分離材
US8741030B2 (en) 2010-02-24 2014-06-03 Kuraray Co., Ltd. Metal complex, and adsorbent, occlusion material and separator material made from same
WO2020230756A1 (fr) 2019-05-13 2020-11-19 学校法人立教学院 Corps structural organométallique
JP7555914B2 (ja) 2019-05-13 2024-09-25 学校法人立教学院 金属有機構造体
CN110628037A (zh) * 2019-09-12 2019-12-31 重庆师范大学 黄色荧光的混配体锰超分子聚合物及其制备方法与应用
CN110628037B (zh) * 2019-09-12 2021-10-26 重庆师范大学 黄色荧光的混配体锰超分子聚合物及其制备方法与应用
CN115850161A (zh) * 2022-11-26 2023-03-28 郑州大学 基于三蝶烯配位自组装四面体超分子笼、制备方法及应用
CN119591816A (zh) * 2024-12-06 2025-03-11 华侨大学 一种三蝶烯改性β-酮烯胺共价有机框架、其制备方法及其用途

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