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Nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and preparation method and application thereof

A technology of bispyrazole methylphenoxymethylimidazole and methylphenoxymethyl is applied in the field of preparation of nitrogen heterocyclic carbene silver complexes, can solve rare problems and the like, and achieve strong fluorescence emission and efficient catalytic activity. Effect

Active Publication Date: 2014-11-19
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The introduction of bispyrazolemethane into nitrogen heterocyclic carbene, the design and synthesis of pyrazolidine functionalized nitrogen heterocyclic carbene and its complexes are still relatively rare

Method used

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  • Nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and preparation method and application thereof
  • Nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and preparation method and application thereof
  • Nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Synthesis of 1-[2-bis(pyrazol-1-yl)methylphenoxymethyl]imidazole

[0015] In a 100mL round bottom flask, add 20mL of ethanol, 2.4g (10mmol) of 2-hydroxyphenylbis(pyrazol-1-yl)methane, 1.53g (10mmol) of 1-chloromethylimidazole hydrochloride and hydroxide Potassium 1.12g (20mmol), then heated and stirred under reflux for 24 hours. Cool to room temperature, filter, and wash the solid with ethanol (3×10 mL), which is the inorganic salt potassium chloride. The filtrate was removed from the solvent, and 20 mL of water was added, extracted with dichloromethane (3×30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The solvent was removed to obtain 1.79 g of a light yellow solid product with a yield of 56%. 1 H NMR (400MHz, CDCl 3 ): δ5.97(s, 2H), 6.32(t, 2H), 6.89(s, 1H), 7.73(s, 1H), 7.94(s, 1H), 6.87(d, 1H), 7.04(t, 1H), 7.32(d, 1H), 7.39-7.45(m, 1H), 7.12(s, 1H), 7.56(d, 2H), 7.66(d, 2H).

[0016] Synthesis of Chloro-N-[2-bis(py...

Embodiment 2

[0022] Synthesis of N-[2-bis(pyrazol-1-yl)methyl]phenoxymethyl-N'-benzyl imidazolium tetrafluoroborate

[0023] In a 100mL round bottom flask, 0.45g (1.0mmol) of chloro N-[2-bis(pyrazol-1-yl)methyl]phenoxymethyl-N'-benzyl imidazolium salt (L1) was dissolved in 10 mL of water, and then 0.14 g (1.3 mmol) of ammonium tetrafluoroborate in 10 mL of aqueous solution was added dropwise to the above reaction mixture, and stirring was continued at room temperature for 3 hours after the addition was complete. It was extracted with dichloromethane (3×10 mL), and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain 0.45 g of a white hygroscopic solid product with a yield of 90%. 1 H NMR (400MHz, CDCl 3 ): δ5.24(s, 2H), 6.00(s, 2H), 6.23(t, 2H), 6.84(d, 1H), 7.15(d, 1H), 6.70-7.07(m, 3H), 7.31- 7.37 (m, 6H), 7.96 (s, 1H), 7.42 (d, 2H), 7.51 (d, 2H), 8.97 (s, 1H).

[0024] S...

Embodiment 3

[0027] The ligand (L1) prepared in Example 1 and the corresponding nitrogen-heterocyclic carbene silver complex (1) were measured for solid fluorescence at room temperature, and the fluorescence emission spectrum intensity of the complex (1) was stronger than that of the corresponding ligand. Significant changes in fluorescence. The excitation wavelength of the ligand (L1) is 295nm and the excitation wavelength of the corresponding complex (1) is 360nm. The solid-state fluorescence diagram is shown in the appendix of the manual. figure 2 .

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Abstract

The invention relates to a nitrogen heterocyclic carbene silver complex based on bispyrazole methyl phenoxy methylimidazole and a preparation method and application thereof. The preparation method of the nitrogen heterocyclic carbene silver complex is as follows: at room temperature in dark conditions, a bispyrazole methyl phenoxy methyl substituted imidazolium salt and silver oxide in the molar ratio of 1 to 0.7 are dissolved in an organic solvent for reaction for 24 hours, then filtered and concentrated to prepare the nitrogen heterocyclic carbene silver complex. The nitrogen heterocyclic carbene silver complex has strong capability of emission fluorescence and catalyzing of coupled reaction of acetylene, amine and aldehyde three components, and can be mainly used in fluorescent materials and organic catalysis technology field.

Description

Technical field: [0001] The invention belongs to the technical field of organic synthesis and organometallic chemistry, and relates to the synthesis and application of nitrogen heterocyclic carbene silver complexes, more specifically chloro 1-[2-bis(pyrazol-1-yl)methylphenoxy Methyl]imidazolium salt and 1-[2-bis(pyrazol-1-yl)methylphenoxymethyl]imidazolium hexafluorophosphate and tetrafluoroborate as precursors of azacyclic carbene silver complexes Preparation method and application. Background technique: [0002] Due to its successful application in coordination chemistry and homogeneous catalysis, azacyclic carbene and its transition metal complexes have become one of the research hotspots in recent years. Among these nitrogen-heterocyclic carbene metal complexes, nitrogen-heterocyclic carbene-silver complexes have received widespread attention. They exhibit structural diversity, are widely used as carbene transfer reagents, and possess potential biological activity as w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/10C09K11/06B01J31/22C07D403/14
Inventor 唐良富李强杨军
Owner NANKAI UNIV
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