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Organic gel material and preparation method thereof

A technology of organogel and xerogel, which is applied in the field of multiple stimuli responsiveness, preparation of organogel, and synthesis of small molecule gelling factor 4-phenyl)-pyrenecarboylhydrazone, which can solve synthesis difficulties and functional Complicated material structure and other issues, to achieve the effect of convenient purification, easy recycling, and non-toxic recycling

Inactive Publication Date: 2017-05-10
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Another technical problem to be solved by the present invention is to provide a method for preparing an organogel material with the advantages of simple structure, short preparation route, and convenient product purification in view of the complex structure and difficult synthesis of existing functional materials.

Method used

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  • Organic gel material and preparation method thereof
  • Organic gel material and preparation method thereof
  • Organic gel material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Synthesis of Gelation Factor and Preparation of Organic Gel Material

[0026] The synthetic steps of gel factor: Weigh 2.0g (0.0051mol) of 3,4,-octyloxybenzoic hydrazide and 1.179g (0.0051mol) of 1-pyrene formaldehyde, put it into a 250mL Erlenmeyer flask, Add 100 mL of absolute ethanol as a solvent, heat to reflux for 6 hours, cool to room temperature after the reaction, filter and dry to obtain a yellow solid. The crude product was recrystallized twice from absolute ethanol. 2.7 g of pure sample 4-(3,4-(octyloxy)phenyl)-pyrenecarboylhydrazone was obtained, with a yield of 87.6%.

[0027] The reaction formula is as follows:

[0028]

[0029] Molecular structure characterization data of materials: 1 H NMR(300MHz,DMSO-d6),(ppm,from TMS):11.94(s,1H),9.645(s,1H),8.753(s,4H),8.20-8.16(d,1H),7.655-7.58 (m,4H),7.30(s,2H),4.10-3.96(m,6H),1.782-1.70(m,6H),1.485(s,6H),1.281(s,24H),0.87(s,9H ).FT-IR(KBr,pellet,cm -1 ): 3433,3170,3065,3034,2926,2857,1675,1637,16...

Embodiment 2

[0031] Example 2 Photoresponse of organogels

[0032] The gelling factor of the present invention exhibits aggregation-induced fluorescence enhancement during the gelation process, such as figure 1 .

[0033] Photoresponse of the organogel: The organogel was irradiated with visible light, and the organogel transformed into a clear tan solution after a certain period of time. The organogel with a concentration of 5.91mg / mL needs to undergo a gel-sol transition after 195min of light; and with the increase of the light time, the fluorescence intensity is obviously weakened, and after the gel-sol transition occurs, the solution basically does not emit light (see figure 2 and image 3 ).

Embodiment 3

[0034] Example 3 Preparation method of xerogel and force response of xerogel

[0035] The organogel obtained in Example 1 was put into a freeze dryer and dried for 40 hours to remove the dimethyl sulfoxide solvent to obtain a xerogel.

[0036] Such as Figure 4 , the color change of the mechanofluorochromic material (xerogel) before and after grinding seen under a 365nm ultraviolet lamp. The xerogel emits blue fluorescence, and when the xerogel is manually and fully rubbed with the rod of a mortar, the fluorescence of the solid changes from blue to green. However, the ground sample was heated at 130°C for 30 minutes and then observed under a UV lamp, and it was found that it returned to the original blue color.

[0037] Depend on Figure 5The fluorescence spectrum shows that the emission peak of the dry gel without external grinding is around 457nm, corresponding to blue fluorescence; the emission peak of the solid after grinding with a mortar is red-shifted to 514nm, corre...

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Abstract

The invention discloses an organic gel material and a preparation method thereof and belongs to the technical field of supramolecular self-assembly. Organic gel is obtained by dissolving a small-molecular compound 4-(3,4-(octaneoxy)phenyl)-pyrene carbonylhydrazone in a dimethyl sulfoxide solvent under the heating condition and then performing cooling to reach room temperature. The prepared organic gel has gathered and induced fluorescence enhancement properties and visible-light response. In addition, xerogel prepared based on the organic gel has a force-sensitive fluorescence phenomenon. The organic gel has the gathered and induced fluorescence enhancement properties and visible light and external force response and has the potential application prospect on the aspects of fluorescence switches, external force detection, sensors and the like.

Description

technical field [0001] The invention belongs to the technical field of supramolecular self-assembly, in particular to the synthesis of small molecule gelling factor 4-(3,4-(octyloxy)phenyl)-pyrenecarboylhydrazone, the preparation method of organogel and multiple stimulus responsiveness. Background technique [0002] Organogels are self-assembled three-dimensional network structures with highly self-organizing properties through intermolecular hydrogen bonds, π-π stacking, hydrophobic interactions, and van der Waals interactions. Stimuli-responsive organogels have the characteristics of showing different physical and chemical properties in response to external physical or chemical stimuli, and have potential application prospects in the fields of template chemistry, sensors, molecular recognition, and drug sustained release. [0003] Because the photochemical reaction is very fast, external light can cause a rapid response in the molecular self-assembly process, and the wave...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C07C249/16C07C251/86B01J13/00
CPCB01J13/0065C07C249/16C09K9/02C09K2211/1007C09K2211/1011C07C251/86
Inventor 白炳莲韦学玉柴青李敏
Owner JILIN UNIV
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