L-glutamine organogel containing 1-cyanotoluylene and preparation method thereof

A cyanostilbene, glutamine technology, applied in the field of supramolecular chemistry, can solve problems such as limited application

Inactive Publication Date: 2011-11-16
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This shortcoming limits the further application of these gels

Method used

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  • L-glutamine organogel containing 1-cyanotoluylene and preparation method thereof
  • L-glutamine organogel containing 1-cyanotoluylene and preparation method thereof
  • L-glutamine organogel containing 1-cyanotoluylene and preparation method thereof

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Embodiment 1

[0029]

[0030] N 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 - Preparation of (4-(1-cyano-2-styryl)phenyl)glutaramide (1):

[0031] Compound 2 (1g, 1.4mmol, synthesized according to literature, "Xue PC, Lu R, Yang XC, et al., Chem. Eur. J., 2009, 15, 9824; Xue PC, Lu R, Zhao L, et al. al., Langmuir, 2010, 26, 6669 ".") and benzaldehyde (0.2g, 1.9mmol) were placed in 50mL of ethanol, heated to reflux at 80°C for 30min, and then added 20 microliters of tetrabutylammonium hydroxide Ethanol solution (concentration is 2mol / L), reflux overnight. Suction filtration, the solid was washed several times with water and ethanol, and then recrystallized twice with ethanol. Vacuum dried to obtain 1.0 g light yellow solid, namely N 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 -(4-(1-cyano-2-styryl)phenyl)glutaramide. Yield: 89%, melting point >200°C.

[0032] H NMR spectrum (500MHz, CDCl 3, TMS): δ=9.14(s, 1H, NH), 7.87(d, J=9.0Hz, 2H), 7.73(d, J=10.5Hz, 2H), 7.61(d,...

Embodiment 2

[0034] Accurately weigh 1 mg of N prepared in Example 1 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 -(4-(1-cyano-2-styryl)phenyl)glutaramide, placed in a glass bottle with a diameter of 1cm and a volume of 10mL with a screw cap, take 1mL of o-dichlorobenzene with a pipette Put it into the bottle, close the screw cap, heat to 120 degrees Celsius to dissolve all the solids, then cool to room temperature naturally, and then stand for 10 minutes to get N with a concentration of 1 mg / mL. 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 - Clear gel system composed of (4-(1-cyano-2-styryl)phenyl)glutaramide and o-dichlorobenzene.

Embodiment 3

[0036] Accurately weigh 1 mg of N prepared in Example 1 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 -(4-(1-cyano-2-styryl)phenyl)glutaramide, placed in a glass bottle with a diameter of 1cm and a volume of 10mL with a screw cap, pipette 0.9mL of dimethyl Put sulfoxide into the bottle, heat to 150 degrees Celsius to dissolve all the solids, add 0.1mL of water to the above solution with a pipette, cover the screw cap, heat to 100 degrees Celsius to redissolve the solids, and then cool naturally to room temperature , and leave it for another 10 minutes to get N with a concentration of 1 mg / m L 1 -((1,3-Di(dodecylcarbamoyl)propylcarbamoyl))-N 5 -(4-(1-cyano-2-styryl)phenyl)glutaramide and DMSO / H 2 A translucent gel system composed of O (volume ratio = 9:1).

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Abstract

The invention belongs to the technical field of super molecular chemistry, and particularly relates to L-glutamine organogel containing 1-cyanotoluylene and a preparation method thereof. The organogel is a mixed system consisting of an organogel agent and a solvent. In the system, the organogel agent is L-glutamine organogel containing 1-cyanotoluylene, and the concentration of gel is 1-5 milligrams / milliliter. The organogel is obtained by dissolving a small molecular organogel agent in an organic solvent or a mixture of an organic solvent and water under a heating condition and cooling to room temperature. The organogel can be used for gelating 12 types of solvents such as toluene, chlorobenzol, dichlorobenzene, methylene dichloride, methanol, a mixture of DMSO (Dimethylsulfoxide) or DMF (Dimethyl Formamide) and water, and the like, and the system represents an aggregation induction fluorescence enhancement phenomenon in the gelating process. Due to the aggregation induction fluorescence enhancement property, the application of the L-glutamine organogel to a temperature-sensitive fluorescent switch becomes possible.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and in particular relates to a 1-cyano-distyryl-containing L-glutamine organogel and a preparation method thereof. Background technique [0002] Molecular self-assembly is a synthetic method for building nanostructures that spontaneously combines molecules into structurally defined aggregates through non-covalent interactions. The key to such a self-assembly process is not a simple superposition of a large number of weak intermolecular forces, but an overall complex synergy. Organogels constructed from small-molecule organogels (LMOGs) have attracted more and more attention in recent years. These thermally reversible soft materials are generally composed of a very small amount of LMOG and a large number of organic solvent molecules, and the rheological behavior of the organogel is similar to that of a solid. People can easily obtain organogels with different structures through ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/44C07C255/30C09K3/00
Inventor 薛鹏冲卢然徐德芳贾俊辉
Owner JILIN UNIV
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