Preparation method and application for amphiphilic naphthoyl diimide gelator

A naphthalene bisimide gel and amphiphilic technology, which is applied in the field of supramolecular chemistry, can solve the problems of naphthalene bisimide synthesis and separation, separation and purification difficulties, harsh reaction conditions, etc., and achieve a simple and efficient synthesis method , easy separation and purification, and mild reaction conditions

Active Publication Date: 2018-02-09
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 naphthalimide groups can form gels in organic solvents, but the synthesis and separation of asymmetric naphthalimides are difficult
At present, the synthesis of asymmetric naphthalene bisimide derivatives has disadvantages such as harsh reaction conditions, many by-products, and difficult separation and purification.

Method used

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  • Preparation method and application for amphiphilic naphthoyl diimide gelator
  • Preparation method and application for amphiphilic naphthoyl diimide gelator
  • Preparation method and application for amphiphilic naphthoyl diimide gelator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The structural formula of a kind of amphiphilic naphthalene diimide gel factor is:

[0034]

[0035] The above-mentioned amphiphilic naphthalene diimide gel factor is synthesized by the following route:

[0036]

[0037] Specifically comprise the following steps in the above-mentioned synthetic method:

[0038] (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 24h). 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, 2mol.L -1 ), heated to reflux, and detected by TLC until the reaction was complete (about 2h). Stop the reaction, remove CH by rotary evapo...

Embodiment 2

[0061] In this embodiment, the amphiphilic naphthalene diimide gel factor and its preparation method are the same as in Example 1. The compound NDI-1 that will be obtained in this embodiment is the amphiphilic naphthalene diimide gel factor Gel was prepared by gelation with solvent toluene by the following method.

[0062] The gelling factor (3.3 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: figure 2 As shown, the test results of the gelation performance of the gelling factor on the solvent toluene are shown in Attached Table 1.

Embodiment 3

[0064] In this embodiment, the amphiphilic naphthalene diimide gel factor and its preparation method are the same as in Example 1. The compound NDI-1 that will be obtained in this embodiment is the amphiphilic naphthalene diimide gel factor Gel was prepared by gelation with solvent xylene by the following method.

[0065] The gelling factor (3.3 mg) and xylene (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 xylene is as follows: image 3 As shown, the test results of the gelation performance of the gel factor on the solvent xylene are shown in Attached Table 1.

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Abstract

The invention belongs to the technical field of supramolecular chemistry, and specifically relates to a preparation method and an application for an amphiphilic naphthoyl diimide gelator. The amphiphilic naphthoyl diimide gelator provided by the invention has a molecular formula of C89H138N4O21, and can enable benzene, toluene, xylene, dimethyl sulfoxide (DMSO) or a tetrahydrofuran solution with awater content of 30% (H2O-THF with a concentration of 30%) to generate gelation at a low concentration (3.3 mg.mL<-1> to 9.5 mg.mL<-1> through a heating-cooling method. Meanwhile, the molecular gel formed by gelation can realize reversible conversion between a solution state and a gel state through the external action of heating-cooling. The gelator provided by the invention has the advantages ofsimple synthesis, easily modified structure, thermal reversibility, large polarity range of a gelated solvent, etc., and has potential application values in fields like catalysis, sensor technologies, drug delivery and chiral separation.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and in particular relates to a preparation method and application of a gel factor capable of gelling an organic solvent or a mixture system of an organic solvent and water at a low concentration. 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 chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06B01J13/00
CPCB01J13/0065C07D471/06
Inventor 裴强丁爱祥
Owner XINYANG NORMAL UNIVERSITY
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