Preparation method and application of naphthalene diimide gelator with symmetric structure

A technology of naphthoyl bisimide gel and structural symmetry, which is applied in the field of supramolecular chemistry and can solve the difficulties in the synthesis and separation of naphthalene bisimide derivatives, harsh reaction conditions, and difficulties in separation and purification of naphthalene bisimide derivatives and other problems, to achieve the effect of simple and efficient synthesis method, easy separation and purification, and simple synthesis method

Inactive Publication Date: 2018-09-07
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Many organic compounds containing naphthoylbisimide groups can form gels in organic solvents, but the synthesis and separation of naphthoylbisimide derivatives are difficult
At present, the synthesis of naphthalimide derivatives has disadvantages such as harsh reaction conditions, many by-products, and difficulty in separation and purification.

Method used

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  • Preparation method and application of naphthalene diimide gelator with symmetric structure
  • Preparation method and application of naphthalene diimide gelator with symmetric structure
  • Preparation method and application of naphthalene diimide gelator with symmetric structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The structural formula of a kind of structurally symmetrical naphthalene diimide gel factor is:

[0032]

[0033] The above-mentioned structurally symmetrical naphthalene diimide gel factor is synthesized by the following route:

[0034]

[0035] Specifically comprise the following steps in the above-mentioned synthetic method:

[0036] (1) methyl gallate (3.68g, 20mmol) and anhydrous K 2 CO 3 (24.8g, 180mmol) was added to 100mL CH 3 To CN, the compound n-dodecane bromide (28.7 mL, 120 mmol) was added with stirring. Heating to reflux, TLC detection, until the reaction is complete (about 24 hours). Stop heating, cool naturally, and remove insoluble matter by suction filtration. Rotary evaporation to remove CH 3 CN, a yellow sticky substance was obtained. Add 150mL CH 3 OH to make it dissolve, while stirring, add NaOH aqueous solution (2.0g, 50mmol, 2molL -1 ), heated to reflux, and detected by TLC until the reaction was complete (about 2 hours). Stop the ...

Embodiment 2

[0051] In this embodiment, the structurally symmetrical naphthalene bisimide gel factor and its preparation method are the same as in Example 1. The compound NDI-1 obtained in this example is the structurally symmetrical naphthalene bisimide gel factor and the solvent benzene Gels were prepared by gelation by the following method.

[0052] The gelling factor (9.8 mg) and benzene (1.0 mL) were placed in a small screw bottle with a height of 5 cm and a diameter of 1.5 cm. Seal the screw bottle, use a water bath to heat the mixing system in the screw bottle until the compound is completely dissolved, then let it stand at room temperature, turn the screw bottle upside down after cooling, no liquid flow phenomenon, that is, a gel is formed. The SEM morphology of the xerogel formed by the gelling factor in benzene is as follows: figure 2 As shown, the test results of the gelation performance of the gelling factor on the solvent benzene are shown in Attached Table 1.

Embodiment 3

[0054] In this embodiment, the structurally symmetrical naphthalene diimide gel factor and its preparation method are the same as in Example 1. The compound NDI-1 obtained in this example is the structurally symmetrical naphthalene bisimide gel factor and the solvent toluene Gels were prepared by gelation by the following method.

[0055] The gelling factor (8.5 mg) and toluene (1.0 mL) were placed in a small screw bottle with a height of 5 cm and a diameter of 1.5 cm. Seal the screw bottle, use a water bath to heat the mixing system in the screw bottle until the compound is completely dissolved, then let it stand at room temperature, turn the screw bottle upside down after cooling, no liquid flow phenomenon, that is, a gel is formed. The SEM morphology of the xerogel formed by the gelling factor in toluene is as follows: image 3 As shown, the test results of the gelation performance of the gelling factor on the solvent toluene are shown in Attached Table 1.

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Abstract

The invention discloses a preparation method and application of a naphthalene diimide gelator with a symmetric structure. The naphthalene diimide gelator with the symmetric structure has a molecular formula: C104H168N4O12 and is capable of gelatinizing cyclohexane, benzene, methylbenzene and dimethylbenzene under low concentration (4.0mg mL<-1>-9.8mg mL<-1>) by using a heating-cooling method. In addition, molecular gel formed after gelatinization is reversible between a solution state and a gel state under an external action of heating-cooling or mechanical oscillation. The gelator provided bythe invention is simple in synthesis and easily-modified in structure, has the advantages such as thermal reversibility, oscillation stimulation responsiveness and the like and has a potential application value in the field such as catalysis, sensing technologies, drug delivery and chiral separation.

Description

technical field [0001] The invention relates to the technical field of supramolecular chemistry, in particular to a preparation method and application of a structurally symmetrical naphthalene bisimide gel factor. Background technique [0002] Some organic small molecular compounds can gel water or organic solvents at a lower concentration, and the formed gel is called organic small molecule gel, and this type of organic compound is called gel factor. Organic small molecule gel is a new type of soft coagulation system. Generally, the gel factor is heated and dissolved in a solvent, and then cooled to room temperature. The bond force interacts, spontaneously aggregates and assembles into a complex three-dimensional network structure, and the solvent molecules are bound in it by surface tension, thereby making it gel. Compared with ordinary polymer gels, organic small molecule gels are easy to chemically modify, have better stimuli responses, are safe, non-toxic, biodegradabl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06B01J13/00
CPCC07D471/06B01J13/0065
Inventor 裴强丁爱祥
Owner XINYANG NORMAL UNIVERSITY
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