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Preparation and application of a supramolecular organogel and its metallogel
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An organogel and supramolecular technology, applied in gel preparation, alkali metal compounds, alkali metal oxides/hydroxides, etc.
Inactive Publication Date: 2021-01-19
NORTHWEST NORMAL UNIVERSITY
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However, there are relatively few studies and literature reports on supramolecular organogels formed by the self-assembly of water-soluble pillar[5]arenes and 1,8-naphthalimide derivatives.
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Embodiment 1
[0065] Example 1. Preparation of supramolecular organogel (WP5-PN-G)
[0066] (1) Synthesis of intermediate (ZM): Add hydroquinone (2.2022 g, 20.0 mmol), anhydrouspotassiumcarbonate (16.56 g, 120 mmol), potassiumiodide (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, filter with suction, add silica gel to mix the sample, spin dry, and purify by column chromatography (petroleumether: ethyl acetate = 50:1), and the obtained white product is 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.
[0067] (2) Synthesis of dibr...
Embodiment 2
[0073] Example 2. Organic supramolecular gel (WP5-PN-G) recognizes Fe 3+ and Cu 2+
[0074] Take 18 parts of a small amount (about 0.01g) of organogel WPN-G on a 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+ , Na + , Cd 2+ , Hg 2+ , Pb 2+ , Ba 2+ , Al 3+ , La 3+ and Eu 3 + of aqueous solution. The fluorescent color change of the gel was then observed under UV light. If the color of the organogel changes from light yellow to black, it means that the addition of Fe 3+ and Cu 2+ solution, accompanied by the corresponding stable metal-organic gels WP5-PN-FeG and WP5-PN-CuG. If the color of the organogel (WP5-PN-G) does not change, it indicates the addition of an aqueous solution of other ions.
Embodiment 3
[0075] Embodiment 3, preparation of metal organogel WP5-PN-FeG
[0076] Take quaternized column[5]arene WP5 (0.014g, 60.11mmol), 1,8-naphthalimide derivative PN (0.006g, 58.00mmol), iron perchlorate hexahydrate (0.0028g, 30.06 mmol), heated together and dissolved in 20mlDMSO-H 2 O (volume ratio 1:1) binary solution, after cooling to room temperature, a stable metal-organic gel WP5-PN-FeG was formed. The organometallic gel has good stability, and the shape of the gel remains unchanged after being placed for several days, and the metal gel has no fluorescence.
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Abstract
The invention discloses a supramolecular organogel formed by self-assembly of quaternized pillar[5]arene (WP5) used as a host and 1,8-naphthalimide (PN) used as a guest. The organogel can form an organic supramolecular gel WP5-PN-G with light-yellow aggregation-state induced fluorescence in DMSO-H2O under exterior-wall pi-pi interaction. When Fe<3+> and Cu<2+> are added into WP5-PN-G, the fluorescence of WP5-PN-G is quenched, so WP5-PN-G can be used for highly-selectively identifying Fe<3+> and Cu<2+>; when F<-> and CN<-> are separately added into fluorescence-quenched metal gels WP5-PN-FeG and WP5-PN-CuG, since F<-> and CN<-> are respectively complexed with Fe<3+> and Cu<2+>, the exterior-wall pi-pi interaction of WP5-PN-G is restored again, so aggregation-state induced fluorescence reappears, so continuous reversible ultrasensitive detection of Fe<3+>, F<->, Cu<2+> and CN<->.
Description
technical field [0001] The present invention relates to a supramolecular organogel, in particular to a quaternized pillar[5]arene (WP5) as the main body and 1,8-naphthalimide (PN) as the guest self-assembled with Supramolecular organogel WP5-PN-G with aggregation induction effect and its preparation method; the present invention also relates to the preparation of supramolecular organometallic gel WP5-PN-FeG and WP5-PN-CuG based on the supramolecular organometallic gel; The invention also relates to the application of the supramolecular organic gel and metal gel in ion detection. 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 ge...
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