Preparation of supermolecule gel factor based on three-column [5] aromatic hydrocarbon and organic gel thereof and application

A technology of supramolecular gel and organogel, applied in the field of organogel and recognition of Hg2+ in fluorescence, supramolecular gel factor and its synthesis, can solve the problem that the stimulus response properties have not been widely studied

Inactive Publication Date: 2018-10-16
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although supramolecular organogels based on pillar[5]arenes have been reported, supramolecular organogels based on tri-pillar[5]arenes and their stimuli-responsive properties have not been extensively investigated.

Method used

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  • Preparation of supermolecule gel factor based on three-column [5] aromatic hydrocarbon and organic gel thereof and application
  • Preparation of supermolecule gel factor based on three-column [5] aromatic hydrocarbon and organic gel thereof and application
  • Preparation of supermolecule gel factor based on three-column [5] aromatic hydrocarbon and organic gel thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, the synthesis of gelling factor JP5

[0034] (1) Synthesis of compound A: 12.4 g p-methoxyphenol (100 mmol), 13.8 g potassium carbonate (100 mmol), 3.3 g potassium iodide (20 mmol), 12.2 g ethyl chloroacetate (100 mmol) were placed in a 500 mL In the round bottom flask, add 400mL of acetone as a solvent, reflux at 60°C for 24h, add an appropriate amount of silica gel after the reaction stops and spin the solvent dry, and use column chromatography (petroleum ether: ethyl acetate = 50:1 ) to obtain a pale yellow liquid ((20.16g, 96%). 1 HNMR (600MHz, CDCl 3 ), δ 6.82 (q, J =9 Hz, 4H, ArH), 4.53 (s, 2H, OCH 2 CO), 4.22 (q, J =7.2 Hz, 2H, OCH 2 ), 3.73 (s, 3H, OCH 3 ), 1.26 (t, J =7.2Hz, 3H, CH 3 ).

[0035] (2) Synthesis of compound PA: 2.76 g of 1,4-dimethoxybenzene (20 mmol), 1.05 g of compound A (5 mmol), and 0.75 g of paraformaldehyde (25 mmol) were placed in a 150 mL round bottom flask, Add 100mL of 1,2-dichloroethane as a solvent, add 2.7 mL o...

Embodiment 2

[0040] Embodiment 2, the preparation of organogel JP5G

[0041] Weigh 0.00125g of gelling factor (JP5) into a 1ml gel bottle, add 25 μL cyclohexanol to the gel bottle, heat to fully dissolve the gelling factor, let stand and cool to room temperature, and form a stable blue Supramolecular organogel JP5G with aggregation-induced fluorescence. The organogel JP5G has a melting temperature of 58-60°C.

Embodiment 3

[0042] Embodiment 3, organogel JP5G is used for identifying Hg 2+

[0043] Use a capillary to take a series of small pieces of gel JP5G and place them on the drip plate, and add aqueous solutions of different cations (C=1mol / L, Hg 2+ , Ca 2+ , Mg 2+ , Ni 2+ , Cr 3+ , Cd 2+ , Pb 2+ , Ag + , Zn 2+ , Ba 2+ , La 3+ , Eu 3+ , Tb 3 + ), so that the liquid surface is just submerged in the gel, and placed under a fluorescent lamp with a wavelength of 365nm to observe the change of its fluorescent color. It was found that only Hg 2+ The addition of cations can quench the blue fluorescence of JP5G, while the addition of other cations has no obvious effect on the fluorescence intensity of JP5G.

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Abstract

The invention discloses preparation of a supermolecule gel factor based on three-column [5] aromatic hydrocarbon. The supermolecule gel factor is a complex organic gel factor which is synthesized fromamide modified column [5] aromatic hydrocarbon and trimesoyl chloride through a nucleophilic substitution reaction and is based on column aromatic hydrocarbon. According to the gel factor, blue organic gel with aggregation state induction florescence can be formed in cyclohexanol through C-H...pi,pi...pi accumulation and Van der Waals' force. In the organic gel, water solutions of Hg<2+>, Ca<2+>,Mg<2+>, Ni<2+>, Cr<3+>, Cd<2+>, Pb<2+>, Ag<+>, Zn<2+>, Ba<2+>, La<3+>, La<3+>, Eu<3+> and Tb<3+> are respectively added, only addition of Hg<2+> can quench blue florescence of the organic gel, and addition of other cationic ions does not remarkably influence fluorescence intensity of the organic gel, so that specific fluorescence detection on Hg<2+> can be achieved, and a detection limit is 1.02*10<-8>M.

Description

technical field [0001] The present invention relates to a supramolecular gelling factor based on three pillars [5] arene and its synthesis; the present invention also relates to an organogel based on the gelling factor and also recognizes Hg in fluorescence 2+ The application of the invention belongs to the field of compound synthesis and the technical field of cation detection. Background technique [0002] Pillar arenes are a kind of cyclic oligomers formed by linking hydroquinone or hydroquinone ether at the para-position of the benzene ring through the methylene group. Since Ogoshi named this macrocyclic molecule with special properties in 2008, pillararene has experienced rapid development from preliminary synthesis, structure exploration, further functionalization, exploration of host-guest complexation properties, and self-assembly research. Its position in supramolecular host-guest chemistry is increasingly prominent. Due to their excellent properties, pillararenes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/38C07C241/04C09K11/06G01N21/64
CPCC07C243/38C07C2603/92C09K11/06C09K2211/1011G01N21/6428G01N2021/6432
Inventor 林奇江晓梅张有明姚虹魏太保
Owner NORTHWEST NORMAL UNIVERSITY
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