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Method for preparing beta, beta'-binary (4-pyridyl) divinylbenzene

A divinylbenzene and pyridyl technology, applied in the beta field, can solve the problems of harsh reaction conditions, many reaction steps, and long reaction time, and achieve the effects of short reaction time, simple device and simple operation.

Inactive Publication Date: 2009-08-26
SUZHOU UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The reaction has many steps, the reaction conditions are harsh, and it needs to be carried out under a strict anhydrous and oxygen-free atmosphere, and the reagents used are expensive
[0005] (2) The article Absorption Spectra.II.Some AldehydeCondensation Products of Methyl Pyridines published by Blout ER et al. discloses a preparation method of a rigid long-chain linear bipyridine compound, (see: Blout ER, Eager VW, J.Am.Chem .Soc 1945,67,1315-1319), using terephthalaldehyde and p-picoline to reflux for 15 hours in the presence of acetic anhydride. And there is a risk of explosion if the acetic anhydride is improperly handled
[0006] (3) The article Synthesis of novel liner exo-bidentatebispyridine ligands and their complexes with silver(I)tetrafluoroborate published by Vatsadze SZ et al. discloses a preparation method of a rigid long-chain linear bispyridine compound, (see: Vatsadze SZ, Nuriev VN , Chernikov AV, Zyk NV, Russian Chemical Bulletin 2002,51,1804), do reactant with p-dibromobenzene and 4-vinylpyridine, take the triphenylphosphine compound of palladium chloride as catalyst, react more than 12 hours, and low yield

Method used

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  • Method for preparing beta, beta'-binary (4-pyridyl) divinylbenzene
  • Method for preparing beta, beta'-binary (4-pyridyl) divinylbenzene
  • Method for preparing beta, beta'-binary (4-pyridyl) divinylbenzene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] First, the palladium catalyst was prepared according to techniques known to those skilled in the art. Palladium chloride and excess hydrazine hydrate were mixed and stirred for about 2 hours, filtered, and the obtained gray solid was vacuum-dried and sealed for storage.

[0027] 3.30 g (10 mmol) of p-diiodobenzene was dissolved in 15 mL of N, N'-dimethylformamide, and 30 mg of palladium catalyst, 2.61 g (25 mmol) of 4-vinylpyridine and 2.53 g of triethylamine were added thereto. g (25mmol), stirring at a temperature of about 100°C, during the reaction process, point the plate to estimate the reaction conversion rate, and the reaction is complete in 6 hours. For the reaction process, see figure 1 .

[0028] After the reaction was terminated, the above-mentioned reaction bottle was vacuumed to remove the reaction solvent N,N'-dimethylformamide to obtain a brownish-yellow solid. The tan solid was washed with water and dried, and then subjected to silica gel column chromat...

Embodiment 2

[0030] Take zinc nitrate hexahydrate (0.15g, 0.5mmol), p-iodobenzoic acid (0.25g, 1mmol) and β, β'-bis(4-pyridyl) divinylbenzene (0.14g, 0.5mmol) into the capacity In a 15mL reactor, add 10mL of water and seal it. The reactor was reacted at a constant temperature of 150-160°C for 3 days, and slowly cooled to room temperature to obtain yellow crystal 2(C 34 h 24 I 2 N 2 o 4 Zn). Excited by light with a wavelength of 304nm for 2, a strong emission peak will appear at 490nm.

[0031] Through Example 2, it can be seen that: β, β'-bis(4-pyridyl) divinylbenzene is used as a metal complex, a cluster compound and a coordination compound with good optical, magnetic, catalytic, adsorption and other properties to be synthesized with metal ions. Rigid linear ligands for polymers.

[0032] Because the coordination polymers formed by the commonly used analogues 4,4'-bipyridine and 1,2-bis(4-pyridyl)ethylene have these functions, and β,β'-bis(4-pyridyl)bis Vinylbenzene has a greater ...

Embodiment 3

[0034] Product 1 was characterized by infrared, hydrogen spectrum, elemental analysis, etc. Compound 2 was characterized by infrared and X-ray single crystal diffraction, and the fluorescence properties of 1 and 2 were studied. The specific results are as follows.

[0035] Product 1:

[0036] IR: v(KBr) / cm -13446m, 3027w, 1592s, 1547m, 1508w, 1420s, 1325w, 1281w, 1217w, 972s, 868w, 832s, 803w, 591s, 557s.

[0037] 1 H NMR (400MHz, d 6 -DMSO, 298K, TMS): δ=8.58 (s, 4H, Py-H), 7.72 (s, 4H, Ph-H), 7.63 (s, 4H, Py-H), 7.58 (s, 2H, CH =CH), 7.34(d, 2H, CH=CH);

[0038] Elemental analysis (C 20 h 16 N 2 ): theoretical value (%): C, 84.48; H, 5.67; N, 9.85;

[0039] Found value (%): C, 84.76; H, 5.59; N, 9.87.

[0040] Compound 2:

[0041] IR: v(KBr) / cm -1 3434m, 3032w, 1613s, 1558s, 1508w, 1432w, 1390m, 1356s, 1201w, 1028m, 969m, 837s, 763s, 618m, 556s, 473m.

[0042] Crystallographic parameters of compound 2 in table 1

[0043]

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Abstract

The invention discloses a method for preparing beta, beta'-binary (4-pyridyl) divinylbenzene, comprising the steps: phenyl-diiodide, 4-vinylpyridine and triethylamine are taken as raw material, and N, N'-dimethyl formamide is taken as solvent, and Heck reaction is carried out under the action of palladium catalyst at the temperature of 90-110 DEG C, so that the crude products of the beta, beta'-binary (4-pyridyl) divinylbenzene can be obtained; after the reaction is completely finished, the products are purified, and pure beta, beta'-binary (4-pyridyl) divinylbenzene can be obtained. The preparation method is simple and easy to do, and has mild reaction condition and extremely high production rate. The beta, beta'-binary (4-pyridyl) divinylbenzene can be taken as ligand of synthetic metal composition, cluster compound and coordination polymer material.

Description

technical field [0001] The present invention relates to a kind of preparation method of rigid long-chain linear bispyridine compound, and the present invention specifically relates to the preparation method of β, β'-di(4-pyridyl) divinylbenzene. Background technique [0002] Rigid bipyridine compounds have good fluorescent properties due to their many conjugated groups, and because they are not easy to bend in spatial arrangement, they are the preferred ligands for the synthesis of porous coordination polymer materials with adsorption properties in recent years. The priority of the properties of the fluorescent material is closely related to the content of the conjugated group of the ligand. The pore size of the porous coordination polymer material depends largely on the length of the ligand molecule. Ligands mainly focus on 4,4'-bipyridine and 1,2-bis(4-pyridyl)ethene, while ligands with more conjugated groups and longer molecules are rarely studied. Therefore, synthesizin...

Claims

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Application Information

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IPC IPC(8): C07D213/127B01J23/44
Inventor 郎建平刘东李红喜陈阳刘雷雷
Owner SUZHOU UNIV
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