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A kind of gemini structure supramolecular gel factor and its preparation method

A supramolecular gel and gemini-type technology, applied in the direction of organic chemistry, can solve the problems of high cost, unfavorable wide application, and insufficient variety of gel materials, etc., and achieve low critical gel transition temperature and low critical gel concentration , Chiral induction promotes the regular arrangement of the system

Active Publication Date: 2019-05-07
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0003] Chinese patent 201510948648.6 discloses a supramolecular gel that can detect anions and cations with high selectivity and multiple targets, which can detect Pb 2+ , Hg 2+ However, the synthesis process of the gelling factor is relatively complicated and the cost is high, which has great limitations.
[0004] Chinese patent CN201410339683.3 discloses a supramolecular nanogel constructed by the coordination of histidine-modified natural polysaccharides and metalloporphyrins. The gel system has pH sensitivity in tumor cells and good biocompatibility and Biodegradable, but the gel is composed of binary components and has a complex structure
On the one hand, this makes the types of gel materials not rich enough, which is not conducive to their wide application; on the other hand, it leads to insufficient understanding of the regularity of gels, making it difficult to further develop smart gel materials with excellent mechanical properties and multifunctionality, which limits their application. Application range

Method used

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  • A kind of gemini structure supramolecular gel factor and its preparation method
  • A kind of gemini structure supramolecular gel factor and its preparation method
  • A kind of gemini structure supramolecular gel factor and its preparation method

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Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: (R 1 for m=8, R 3 for R 2 for )

[0033] 0.1mol L-alanine, 0.05mol Na 2 CO 3 Put the two raw materials into a three-necked flask, add 200.0mL of distilled water, stir at room temperature to dissolve, slowly add dropwise methanol solution containing 0.1mol pyridine-4-carbaldehyde, methanol 50mL, stir at room temperature for 5h, cool to -4°C, slowly add 0.4mmol NaBH 4 , stirred and reacted for 12 hours, adjusted the pH to 5-6, raised to room temperature and continued to stir for 3 hours, rotary evaporated to dryness, heated and dissolved with a large amount of absolute ethanol at 50°C and filtered, and the filtrate was rotary evaporated to obtain N-(4-pyridine methyl)-L-alanine.

[0034] FT-IR: (cm -1 ): 3375(NH), 3225(OH), 3019(CH), 1720(C=O), 1650(C=N).

[0035] 1 H-NMR (500MHz, DMSO): δ8.597~8.606 (d, J=4.5Hz, 2H, C 5 h 4 N), 8.529~8.541 (d, J=6Hz, 2H, C 5 h 4 N), 4.295~4.300 (d, J=2.5Hz, 2H, -CH 2 -),3.735~3.778(q,1H,CH),1.525~1.539(d,...

Embodiment 2

[0040] Embodiment 2: (R 1 for m=12,R 3 for R 2 for )

[0041] 0.1mol L-valine, 0.05mol Na 2 CO3 Put the two raw materials into a three-necked flask, add 200mL of distilled water, stir at room temperature to dissolve, slowly add dropwise methanol solution containing 0.1mol benzaldehyde, methanol 50mL, stir at room temperature for 5h, cool to -4°C, slowly add 0.4mmol NaBH 4 , stirred and reacted for 12 hours, adjusted the pH to 5-6, raised to room temperature and continued to stir for 2 hours, rotary evaporated to anhydrous, added ethanol, heated to dissolve and filtered, and the filtrate was rotary evaporated to obtain N-(benzyl)-L-valine.

[0042] FT-IR (cm -1 ):3575(NH), 3400(O-H), 1650(-C=N-), 1600(-C=C-).

[0043] 1 H-NMR(500MHz,DMSO):δ7.2746~7.3243(q,4H,C 6 h 4 ), 7.2011~7.2284 (d, J=13.6Hz1H, C 6 h 4 ),3.456~3.728(dd,2H,-CH 2 -), 2.768~2.780(d, J=6Hz, 1H, CH), 1.766~1.940(m, 1H, -CH(CH 3 ) 2 ), 0.910~0.933 (d, J=11.5Hz, 6H, -CH 3 ).

[0044] Dissolve ...

Embodiment 3

[0048] Embodiment 3: (R 1 for m=12,R 3 for R 2 for )

[0049] 0.1mol L-valine, 0.05mol Na 2 CO 3 Put the two raw materials into a three-necked flask, add 200mL of distilled water, stir at room temperature to dissolve, slowly add dropwise methanol solution containing 0.1mol pyridine-4-carbaldehyde, 50mL of methanol, stir at room temperature for 5h, cool to -4°C, and slowly add 0.4mol NaBH 4 , stirred and reacted for 12 hours, adjusted the pH to 5-6, raised to room temperature and continued to stir for 5 hours, rotary evaporated to anhydrous, added ethanol, heated to dissolve and filtered, and the filtrate was rotary evaporated to obtain N-(4-pyridylmethyl)-L-valine .

[0050] FT-IR (cm -1 ;): 3385(NH), 3255(OH), 3069(CH), 2987(CH), 1690(C=O), 1667(C=C), 1430(C=N).

[0051] 1 H-NMR (500MHz, DMSO): δ8.492~8.504 (d, J=6Hz, 2H, C 5 h 4 N), 7.362~7.372 (d, J=5Hz, 2H, C 5 h 4 N),3.582~3.903(dd,2H,-CH 2 -),2.828~2.839(d,J=5.5,1H,-CH),1.879~1.944(m,1H,-CH(CH 3 ) 2 ...

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Abstract

The invention discloses supramolecular gelator of a gemini type structure and a preparation method of the supramolecular gelator. The preparation method of the supramolecular gelator comprises the following steps that 1, chiral amino acid and aromatic formaldehyde generate an imine reaction and are subjected to reaction to obtain a chiral amino acid arene derivative; 2, the chiral amino acid arene derivative obtained in the step1 and aliphatic long-chain diamine are subjected to amide condensation to obtain the supramolecular gelator of the gemini type structure. The gelator can be prepared into supramolecular gel with multiple metal ions, has the significant responsiveness to outside stimuli such as mechanical stress, pH and temperature and can be applied to the fields of sensors, slow releasing, adsorption and the like.

Description

technical field [0001] The invention belongs to the technical field of intelligent responsive gel soft material development, and in particular relates to a gemini-structure supramolecular gel factor and a preparation method thereof. Background technique [0002] Supramolecular gel is a semi-solid, semi-liquid soft matter material formed based on the self-assembly of low-molecular-weight gelling agent molecules to form nanostructures while solidifying solvent molecules. On the basis of maintaining the inherent physical and chemical properties of solid materials and liquid materials, this kind of materials also has many special functions such as stimuli response and self-healing. Different from polymer gels, the gelling factors constituting supramolecular systems have accurate molecular weights, are easy to design and modify, and have richer assembly architectures. With the continuous deepening of research on supramolecular chemistry, people can connect various smart groups i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/38C07C237/10C07D403/14
CPCC07C237/10C07D213/38C07D403/14
Inventor 杜飞杨勇张肖阳肖婷婷费林王小凤
Owner NANJING UNIV OF SCI & TECH
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