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Ultramolecular gel based on functional column [5] arene and application thereof to recognition of ferric ion and L-Cys

A functional, supramolecular technology, applied in chemical instruments and methods, analytical materials, material excitation analysis, etc., to achieve the effect of simplifying the detection process

Inactive Publication Date: 2018-05-25
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, there are still great challenges in the study of bis-naphthalimide-functionalized supramolecular organogels based on pillar[5]arenes
In addition, there are relatively few reports on supramolecular columnar arene gels driven by π-π stacking.

Method used

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  • Ultramolecular gel based on functional column [5] arene and application thereof to recognition of ferric ion and L-Cys
  • Ultramolecular gel based on functional column [5] arene and application thereof to recognition of ferric ion and L-Cys
  • Ultramolecular gel based on functional column [5] arene and application thereof to recognition of ferric ion and L-Cys

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, the synthesis of supramolecular organogelatin factor MP5

[0045] (1) Synthesis of intermediate (ZM): Add hydroquinone (2.2022 g, 20.0 mmol), anhydrous potassium carbonate (16.56 g, 120 mmol), potassium iodide (6.64 g, 40 mmol) into a 500 mL round bottom flask, respectively , 1,6-dibromohexane (39.035 g, 160 mmol) and 400 mL of acetone, heated under nitrogen (65 °C) and stirred under reflux for three days. After the reaction was completed, suction filtered, mixed with silica gel, spin-dried, and purified by column chromatography (petroleum ether: ethyl acetate = 50:1), and the obtained white product was ZM. Yield: 80%, melting point: 97-102°C. 1 H NMR (600 MHz, Chloroform- d ) δ / ppm: 6.81 (s, 4H), 3.90(t, 4H), 3.42 (t,4H), 1.89 (m, 4H), 1.77 (m, 4H), 1.49 (m, 8H). 13 C NMR (CDCl 3 , 151 MHz), δ / ppm: 153.14, 115.39, 68.35, 33.79, 32.68, 29.19, 27.92, 25.29. ESI-MS m / z: [ZM+H] + Calcd for C 18 h 29 Br 2 o 2 , 437.05; Found 437.01.

[0046] (2) S...

Embodiment 2

[0050] Example 2. Preparation of supramolecular organogel (MP5-G)

[0051] Weigh MP5 (0.01g, 7.16×10 -6 mol) into 0.2 mL cyclohexanol, fully dissolved under heating to obtain a transparent solution; when cooled to room temperature, the solution formed a stable condensed yellow gel.

Embodiment 3

[0052] Example 3, organogel (MP5-FeG) recognition experiment Fe 3+

[0053] Take 18 parts of a small amount (about 0.01g) of organogel MP5-FeG on the white drip plate, and add Mg to these organogels respectively 2+ , Ca 2+ , Cr 3+ , Fe 3+ ,Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Ag + , Cd 2+ , Hg 2+ , Pb 2+ , Ba 2+ , Al 3+ , La 3+ and Eu 3+ aqueous solution (1moL / L). The fluorescent color change of the gel was then observed under UV light. The color of the organogel changes from yellow to black, indicating that the addition of Fe 3+ solution, the color of the organogel does not change, indicating that the aqueous solution of other ions has been added.

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Abstract

The invention discloses an ultramolecular gelator MP5 based on naphthalimide functional column 5 arene. The gelator can form organic ultramolecular gel MP5-G with yellow aggregation induced fluorescence in a cyclohexanol solution under the action of pi-pi; the organic ultramolecular gel can be used for detecting Fe<3+> with high selectivity and super sensitivity: when ions such as Fe<3+>, Hg<2+>,Ag<+>, Ca<2+>, Cu<2+>, Co<2+>, Ni<2+>, Cd<2+>, Pb<2+>, Zn<2+>, Cr<3+> and Mg<2+> are added into the MP5-G, fluorescence is quenched only by the Fe<3+>, and stable metal gel MP5-FeG is formed. When L-Cys is added into the fluorescence-quenched metal gel, the L-Cys and the Fe<3+> are complexed to recover the pi-pi action again among the MP5-G, so that aggregation induced fluorescence appears again,and continuous reversible ultrasensitive detection of the Fe<3+> and the L-Cys is realized.

Description

technical field [0001] The present invention relates to a supramolecular organogel based on functionalized column [5] aromatic hydrocarbons, in particular to a functionalized column [5] aromatic hydrocarbon supramolecular gel based on dinaphthalimide; the present invention also relates to Supramolecular organogels involved in the single selective fluorescence recognition of Fe 3+ The invention relates to the application of cysteine ​​L-Cys recognition and continuity, and belongs to the field of organogel. Background technique [0002] Organogel is a supramolecular (soft) material formed by self-assembly of low-molecular-weight organic compounds (gelling factors) in organic solvents through weak intermolecular interactions such as hydrogen bonds, van der Waals forces, and π-π stacking interactions. This material has the unique advantages of solid materials and liquid materials at the same time: the gel molecules maintain their own chemical properties and can carry out some r...

Claims

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Application Information

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IPC IPC(8): C08G83/00C09K11/06G01N21/64
CPCC08G83/008C09K11/06C09K2211/1416C09K2211/1466G01N21/6428
Inventor 张有明李永福林奇仲开鹏陈晓鹏朱伟魏太保姚虹
Owner NORTHWEST NORMAL UNIVERSITY
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