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Imidazole magnetic ionic liquid containing perylene bisimide structure, and preparation method and application of imidazole magnetic ionic liquid

A magnetic ionic liquid, perylene imide technology, applied in the application of biological imaging, imidazole magnetic ionic liquid, magnetic ionic liquid synthesis containing perylene imide structure, the application field of in vivo nuclear magnetic resonance imaging, can solve the problem Problems such as difficult compound application and poor solubility of PDI achieve good biocompatibility, high atom utilization and simple method

Active Publication Date: 2020-11-06
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor solubility of PDI also makes it difficult to apply this type of compound (M. Sunet al., Nanoscale, 2016, 8, 5302-5312.)

Method used

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  • Imidazole magnetic ionic liquid containing perylene bisimide structure, and preparation method and application of imidazole magnetic ionic liquid
  • Imidazole magnetic ionic liquid containing perylene bisimide structure, and preparation method and application of imidazole magnetic ionic liquid
  • Imidazole magnetic ionic liquid containing perylene bisimide structure, and preparation method and application of imidazole magnetic ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthesis of intermediate product a, its chemical structure is as follows:

[0061]

[0062] Weigh 3,4,9,10-perylenetetracarboxylic dianhydride (5mmol, 1.9616g), 6-amino-1-hexanol (20mmol, 2.3438g) and imidazole (20g), place in an oil bath and keep the reaction at React at 150°C for 36h. After the reaction was completed, the product was washed with excess acetone several times, and after vacuum drying for 24 h, a purple-black solid product was obtained. Yield: 98%. figure 1 is the NMR spectrum of a ( 1 H-NMR, 400Hz, CDCl 3 ).

[0063] 1 H NMR (400MHz, CDCl 3 )δ: 8.84–8.75 (multiplet, hydrogen Ar-H on the benzene ring), 4.42 (triplet), 3.87 (triplet), hydrogen-CH of the methylene group connected to the hydroxyl group 2 -OH, 4.29 (triplet, hydrogen N-CH of methylene connected to nitrogen element 2 -), 1.89-1.77 (multiple peaks, the hydrogen N-CH on the methylene separated from the nitrogen element by a methylene 2 -CH 2 -), 1.76–1.68 (multiple peaks, hydr...

Embodiment 2

[0065] The synthesis of intermediate product b, its chemical structure is shown below:

[0066]

[0067] The intermediate product a (4mmol, 2.3627g) was weighed and added to 40mL of toluene, and an aqueous solution of hydrogen bromide of 8 times the number of moles was added to the suspension. The reaction was heated to reflux and maintained at reflux for 36h, and the reaction temperature was 120 degrees Celsius. After the reaction was completed, the reaction was cooled to room temperature, and the product was washed with acetone for several precipitations. After vacuum drying for 24 h, the product was obtained as a purple-red solid. Yield: 94%. figure 2 is the NMR spectrum of b ( 1 H-NMR, 400Hz, CDCl 3 ).

[0068] 1 H NMR (400MHz, CDCl 3 )δ: 8.81 (quartet, hydrogen Ar-H on the benzene ring), 4.28 (triplet, hydrogen-CH of methylene connected to bromine element 2 -Br), 3.43 (triplet, hydrogen N-CH of methylene connected to nitrogen element 2 -), 1.97 – 1.86 (multip...

Embodiment 3

[0070] The synthesis of intermediate product c, its chemical structure is shown below:

[0071]

[0072] Intermediate product b (2mmol, 1.4329g) was weighed and added to a 25mL round bottom flask, 1-methylimidazole (40mmol, 3.2mL) was added to the flask and 5mL of acetone was added. Place in a water bath and keep the reaction at 90°C for 24 hours. After the reaction was completed, the solvent was removed under reduced pressure by a rotary evaporator, and the crude product was precipitated with diethyl ether several times. After vacuum drying for 24 h, the product was obtained as a purple solid. Yield: 100%. image 3 is the NMR spectrum of c ( 1 H-NMR, 400Hz, DMSO-d 6 ).

[0073] 1 H NMR (400MHz, DMSO-d 6 )δ: 9.21 (singlet, hydrogen N-CH-N on the imidazole ring), 8.45-7.89 (multiplet, hydrogen Ar-H on the benzene ring), 7.82 (singlet, hydrogen N on the imidazole ring -CH-CH-N), 7.74 (singlet, hydrogen N-CH-CH-N on the imidazole ring), 4.21 (triplet, and imidazole rin...

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Abstract

The invention discloses imidazole magnetic ionic liquid containing a perylene bisimide structure, and a preparation method and application of the imidazole magnetic ionic liquid. According to the preparation method, a perylene bisimide derivative containing the perylene bisimide structure is obtained through multi-step chemical reactions and then undergoes a complexation reaction with metal inorganic salt so as to obtain the imidazole magnetic ionic liquid containing the perylene bisimide structure. The imidazole magnetic ionic liquid can be absorbed by living cells and realizes effective cellfluorescence imaging at an extremely low concentration. In addition, the imidazole magnetic ionic liquid can form a certain aggregation structure in water due to a pi-pi accumulation effect, so the imidazole magnetic ionic liquid can be selectively enriched at a tumor site of a living animal and shows a nuclear magnetic resonance imaging effect. According to a technical scheme, the invention provides a novel, feasible and efficient synthesis method for the magnetic ionic liquid; the method is mild in reaction conditions, simple in process and high in atom utilization rate; and the magnetic ionic liquid is good in biocompatibility and low in biotoxicity and has huge application prospects in the aspects of fluorescent probes and nuclear magnetic imaging.

Description

technical field [0001] The invention belongs to the technical field of ionic liquids, more specifically, relates to a method for synthesizing a magnetic ionic liquid containing a peryleneimide structure, and its application in biological imaging; more specifically, relates to a method containing a peryleneimide An imine-structured imidazole-based magnetic ionic liquid, and its application in the field of cell imaging and in vivo nuclear magnetic resonance imaging. Background technique [0002] Due to their high selectivity, high sensitivity and excellent photoelectric properties, fluorescent materials have been widely used in various fields, such as analytical chemistry, organic pigments, and biological sciences (L.Hou et al., Analytical Chemistry, 2018, 90, 7122-7126.). Among them, a very important application is as a fluorescent staining agent for cells (H. Kobayashi et al., Chemical Reviews, 2009, 110, 2620-2640.). So far, most fluorescent molecules require relatively h...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06H01F1/44G01N21/64
CPCC07D471/06C09K11/06H01F1/44G01N21/6428C09K2211/1029C09K2211/1044
Inventor 任丽霞于晓亮袁晓燕
Owner TIANJIN UNIV
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