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Photoluminescent room-temperature ionic liquid preparation method

A room temperature ionic liquid and photoluminescence technology, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of lack of preparation methods, high thermal stability, high melting point, etc., and achieve simple, feasible and thermally stable preparation methods The effect of high resistance and low melting point

Active Publication Date: 2015-09-23
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the shortcomings of existing photoluminescence room temperature ionic liquids such as high melting point and lack of simple and feasible preparation methods, the present invention provides a preparation method of a photoluminescence room temperature ionic liquid. The method is simple to operate, and the prepared ionic liquid is in solution It exhibits good photoluminescence behavior in both state and solvent-free conditions, and has high thermal stability, low melting point, adjustable viscosity and solubility

Method used

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  • Photoluminescent room-temperature ionic liquid preparation method
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  • Photoluminescent room-temperature ionic liquid preparation method

Examples

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Embodiment 1

[0046] 1. Add 20 milliliters of thionyl chloride to a round-bottomed flask containing 2.0 grams of 2-naphthoic acid, stir at room temperature for 6 hours, remove thionyl chloride under reduced pressure, add 10 milliliters of dichloromethane, add N-(3- Aminopropyl) imidazole dichloromethane solution (1.4 milliliters dissolved in 15 milliliters of dichloromethane) and 1 mole per liter of sodium hydroxide aqueous solution (10 milliliters), stirred at room temperature for 12 hours, separated to remove the aqueous phase, and collected dichloromethane Methane phase, dichloromethane was removed under reduced pressure, 50 ml of cold water was added, extracted three times with chloroform (20 ml each time), the chloroform phase was combined, dried over anhydrous magnesium sulfate, suction filtered, chloroform was removed under reduced pressure, and CH 3 OH / CH 2 Cl 2 (V CH3OH =15%, containing 0.1% ammonia water) mixed solvent was used as eluent to carry out silica gel column chromatogr...

Embodiment 2

[0051] On the basis of Example 1, the 2-butyl-1-octanol in step 2. is replaced with 2-hexyl-1-decanol, the reaction time in step 3. is adjusted to 4 days, and other conditions are unchanged, to obtain 1-(3-(2-naphthoyl)propyl)-3-(2-hexyldecyl)-1H-imidazole-3-bromide salt, the yield is 38%, its 1H NMR and electrospray mass spectrometry results are shown in figure 2 and Image 6 , and the thermogravimetric analysis results are shown in Figure 9 b, The results of differential scanning calorimetry are shown in Figure 10 b, Rheological measurements are shown in Figure 12-Figure 14 , the photoluminescence behavior in ethanol solution (0.1mol / L) is shown in Figure 17 , the photoluminescence behaviors under solvent-free conditions and on various solid substrates are shown in Figure 18 b and Figure 19 .

Embodiment 3

[0053] On the basis of Example 1, the 2-butyl-1-octanol in step ② is replaced with 2-octyl-1-dodecanol, the reaction time in step ③ is adjusted to 5 days, and other conditions remain unchanged , to get 1-(3-(2-naphthoyl)propyl)-3-(2-octyldodecyl)-1H-imidazole-3-bromide salt, the yield was 37%, and its 1H NMR and electrospray mass spectrometry results are shown in image 3 and Figure 7 , and the thermogravimetric analysis results are shown in Figure 9 c, The results of differential scanning calorimetry are shown in Figure 10 c, The rheological measurement results are shown in Figure 12-Figure 14 , the fluid properties at room temperature are shown in Figure 11 , the photoluminescence behavior under solvent-free conditions is shown in Figure 18 c, d, e.

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Abstract

The invention relates to a photoluminescent room-temperature ionic liquid preparation method. The photoluminescent room-temperature ionic liquid preparation method includes that under an action of thionyl chloride, carboxyl-functionalized naphthaline (pyrene) is converted into naphthyl (pyrenyl) carbonyl chloride, using the naphthyl (pyrenyl) carbonyl chloride to interact with amino imidazole (pyridine) to generate intermediate naphthoyl (pyrene acid) aminoimidazole (pyridylamine); in the presence of triphenylphosphine and carbon tetrabromide, branched alkyl alcohol is converted into branched alkyl halohydrocarbon, and the intermediate naphthoyl (pyrene acid) aminoimidazole (pyridylamine) and the branched alkyl halohydrocarbon are subjected to quaterisation reaction to generate naphthaline-ring-contained (pyrene-ring-contained) photoluminescent room-temperature ionic liquid. The generate naphthaline-ring-contained (pyrene-ring-contained) photoluminescent room-temperature ionic liquid is novel in structure, high in heat stability, low in melting point and adjustable in viscosity and solubility, has photoluminescent characteristics in a solution or in a solvent-free condition and is applicable to the field of fluorescent labels, photoelectric devices and the like.

Description

technical field [0001] The invention belongs to the field of new materials, in particular to a preparation method of a photoluminescent room temperature ionic liquid. Background technique [0002] Organic materials with photoluminescent properties have been widely concerned and practically used in human production and life, although a series of new photoluminescent materials such as rare earth complexes, metal nanoclusters and various quantum dots have emerged in recent years. , organic molecules based on π-conjugated structures still occupy an irreplaceable position in photoluminescent materials. Generally, such organic molecules have good photoluminescence behavior only in solution state, while under solvent-free conditions, the luminescence is quenched due to the strong π-π interaction between π-conjugated groups. , thus greatly limiting their practical applications. The development of new organic molecules with good photoluminescent behavior under solvent-free conditio...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D233/61C07D213/04
Inventor 郝京诚李洪光朱洪霞陈孟军周升菊
Owner SHANDONG UNIV
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