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Functional ionic liquid and preparation method thereof

An ionic liquid, functionalized technology, applied in chemical instruments and methods, preparation of sulfonic acid amides, organic chemistry, etc., can solve the problems of difficult coordination of metal ions and no lone pair electrons.

Inactive Publication Date: 2011-09-14
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a novel functionalized ionic liquid in view of the current ionic liquids that do not contain lone pairs of electrons and are not easy to coordinate with metal ions. Phenanthroline, functionalizing ionic liquids to donate lone pairs of electrons

Method used

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  • Functional ionic liquid and preparation method thereof
  • Functional ionic liquid and preparation method thereof
  • Functional ionic liquid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] ①. Dissolve 30g of phenanthroline in 150mL of concentrated sulfuric acid (65%-68%) and add 80mL of fuming nitric acid (86%-97.5%) dropwise under stirring at 168°C. Slowly pour the mixture into more than 2Kg of crushed ice to cool it below zero, then add NaOH to adjust the pH to about 7, filter and wash with water to obtain 5-nitro-1,10-phenanthroline, which is recorded as Phen-NO 2 (32.7782g).

[0038] ②, 1g Phen-NO 2 Dissolve in 10mL ethanol and add 200mg of activated carbon (5%Pd / C) loaded with 5% palladium metal powder by mass percentage, then mix 1.5mL hydrazine with 10mL ethanol, drop this at room temperature, then mix the solution at 70 Reflux under stirring at ℃ for 6-8 hours, filter and concentrate the filtrate to half of its original volume, then add 500mL of water and let stand until all 5-amino-1,10-phenanthroline is precipitated, filter and then purify in chloroform to obtain a yellow-green color The solid is put into a vacuum drying oven for drying and re...

Embodiment 2

[0049] The methylimidazole in step ④ was replaced with butylimidazole (commercially available), the ionic liquid was denoted as Phen-bmim (X=Cl, n=3, molecular weight=395.68), and the remaining conditions were the same as in Example 1.

[0050] The NMR of the tested ionic liquid is as follows:

[0051] 1 H NMR (DMSO): δ11.291(s, 1H), δ9.383(s, 1H), δ9.166(m, 1H), δ9.070(m, 1H), δ8.927(d, 1H) , δ8.487(m, 1H), δ8.203(s, 1H) δ7.915(s, 1H), δ7.876(m, 2H), δ7.771(m, 1H), δ5.585(s , 2H), δ4.291 (t, 2H), δ1.825 (t, 2H), δ1.310 (m, 2H), δ0.932 (s, 3H).

[0052] The physical and chemical parameters of the material tested are as follows:

[0053] Excitation spectrum (detection wavelength: 612nm): 200-480nm

[0054] Figure 4 , 5, and 6 are the excitation, emission, and lifetime spectrograms in Example 2, respectively; the data of this rare earth / ionic liquid luminescent material are shown. The characteristic peak of europium can be well seen in the emission diagram, indicating tha...

Embodiment 3

[0056] Dissolve 10mmoL imidazole in 8mL tetrahydrofuran, 15mmoL sodium hydride in 4mL tetrahydrofuran, add the imidazole solution dropwise into the tetrahydrofuran solution of sodium hydride, a large number of bubbles are generated, stir at room temperature for 1 hour after the dropwise addition, add 0.3mmoL tetrabutylammonium iodide The system was evacuated and filled with nitrogen, and 10mmoL of bromoheptane dissolved in 6mL of tetrahydrofuran was added to the system and stirred at room temperature for 18 hours, then filtered with suction, and the filtrate was rotary evaporated, extracted with ether and water, and heptanimidazole was obtained.

[0057] The methylimidazole in step ④ in Example 1 was replaced by heptanimidazole, and the ionic liquid was denoted as Phen-ILC7 (X=Cl, n=6, molecular weight=437.77), and the rest of the conditions were the same as in Example 1.

[0058] The NMR of the tested ionic liquid is as follows:

[0059] 1 H NMR (CDCl 3 ): δ11.537(s, 1H), δ...

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Abstract

The invention relates to a functional ionic liquid and a preparation method thereof. The structural formula of the ionic liquid is disclosed in the specification, wherein X<-> is Cl<-> (chloride ion), [BF4]<-> (tetrafluoroborate ion), [PF6]<-> (hexafluorophosphate ion) or [Tf2N]<-> (bistrifluoromethanesulfonimide ion), and n=0-15. After being introduced to the cation alkyl side chain of the ionicliquid, a phenanthroline group can coordinate with some metallic ions to form metallic coordination compounds, and can absorb energy and transfer the absorbed energy to the metallic ions so as to coordinate with rare earth ions, thereby being used for preparing a rare earth compound / ionic liquid material. The prepared material has the advantages of colorful emitted light, high color purity, long fluorescence lifetime and high quantum efficiency, and is applicable to the fields of display, new light sources, X-ray intensifying screens and the like.

Description

Technical field: [0001] The invention belongs to the field of ionic liquids, and relates to heterocyclic compounds that can be used as ionic liquids, in particular to a functionalized ionic liquid and a preparation method thereof. Background technique [0002] Ionic liquids generally consist of salts of organic cations. Organic cations are generally bulky and asymmetric, such as: N-methyl-N-alkylpyridinium, N-alkylpyridinium, 1-alkyl-3-alkylimidazolium and tetraalkylammonium ions. Ionic liquids are considered to be the most promising solvents in green chemistry and cleaning processes because of their non-volatility, wide liquid range, high electrical conductivity, high thermal stability, and adjustable properties. [0003] There are many kinds of ionic liquids, but most of the functionalized ionic liquids currently synthesized do not contain lone pairs of electrons and are not easy to coordinate with metal ions. [0004] O-phenanthroline has a good planar structure and a s...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07C311/03C07C303/40C09K11/06
Inventor 王弋戈刘欢欢李焕荣
Owner HEBEI UNIV OF TECH
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