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Anion cage compound with fluorescent property and synthesis method thereof

A cage compound and anion technology, applied in the field of anion cage compound and its synthesis, can solve the problems of host-guest properties and application limitations

Active Publication Date: 2021-09-07
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is extremely limited in the study of the host-guest properties and applications of these assemblies

Method used

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  • Anion cage compound with fluorescent property and synthesis method thereof
  • Anion cage compound with fluorescent property and synthesis method thereof
  • Anion cage compound with fluorescent property and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of compound a:

[0046] Silicon tetrachloride (10mL, 0.09mol) was added dropwise into 40mL dry ethanol solution containing 4-nitroacetophenone. A large number of precipitates were generated immediately, and the mixed solution was refluxed for 10 h. Then cooled to room temperature, the reaction solution was added to 50mL NH 4 Cl aqueous solution, stirred for 10 min. The crude product of compound a was obtained by suction filtration and drying, which was directly used for the preparation of compound b.

Embodiment 2

[0048] Preparation of compound b:

[0049] The crude compound a was directly added to 100 mL of ethanol, and Pd / C 10% (0.4 g, cat.) was added. 80% N was added dropwise to the reaction system under reflux 2 h 4 ·H 2 O (20 mL). After reflux for 10 h, diatomaceous earth was added to remove Pd / C by suction filtration, the filtrate was cooled, and a yellow solid was obtained by suction filtration, which was recrystallized from ethanol and dried in vacuo to obtain compound b as a white solid (2.5 g, 7 mmol, 71%). 1 H NMR (400MHz, DMSO-d 6 ,ppm):δ7.48(s,2H,H3),7.46(s,1H,H1),6.67(d,J=7.6Hz,2H,H2),5.23(s,2H,Ha).ESI-MS :m / z 352.1803[M+H]+

Embodiment 3

[0051] Preparation of compound c:

[0052] Add dropwise 20 mL of b (0.35 g, 1 mmol) dissolved in 15 mL of THF solution dissolved in o-nitroisocyanic acid (0.59 g, 3.6 mmol), reflux for 6 h, cool, filter with suction, wash with toluene and diethyl ether, Compound c was obtained as a yellow solid (0.78 g, 0.93 mmol, 93%). 1 H NMR (400MHz, DMSO-d 6 , ppm): δ10.03(s,1H,Hb),9.67(s,1H,Ha),8.35(d,J=8.8Hz, 1H,H7),8.13(d,J=8.0Hz,1H,H4 ),7.86(s,1H,H1),7.83(s,2H,H3),7.73(t,J=7.4Hz,1H,H5),7.65(d,J=7.6Hz,2H,H2), 7.23( t,J=7.0Hz,1H,H6). 13 C NMR (100MHz, DMSO-d 6 , ppm): 151.81 (CO), 141.07 (C), 138.99 (C), 137.67 (C), 135.06 (C), 134.91 (C), 134.25 (CH), 127.58 (CH), 125.47 (CH), 122.89 (CH),122.59(CH), 122.33(CH),118.86(CH).IR(KBr,ν / cm -1 ):3319(NH),1652(CO), 1585,1498,1435,1340,1276(NO2),1190,1144,829,781,740,648. ESI-MS: m / z 844.2489,[M+H] + ,866.2298,[M+Na]+.

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Abstract

The invention discloses an anion cage compound with a fluorescent property and a preparation method thereof, which aim to construct a series of tetrahedral cage structures based on phosphate anion coordination in order to overcome the defect that currently reported supramolecular cage structures constructed by anion coordination lack more direct detection signals. And a series of fluorescent materials responding to halogenated alkane and Freon gas molecules are obtained by utilizing the cage-shaped structures to identify a series of halogenated alkane and Freon molecules. A ligand is reasonably designed, and the ligand and phosphate anions are self-assembled to form an anion tetrahedral cage with a fluorescent property. The tetrahedral cage can capture and respond to a series of halogenated alkane and Freon molecules harmful to the environment, and is of great significance to environmental protection, especially air protection.

Description

technical field [0001] The invention relates to the field of synthesis of ionic compounds, in particular to an anionic cage compound with fluorescent properties and a synthesis method thereof. Background technique [0002] Confined spaces with multifaceted structures have been attracting the attention of chemists due to their wide applications in recognition and separation of guest molecules, stabilization of reaction intermediates and unstable molecules, drug transport, biorecognition, and catalysis. Many researchers have been persistently constructing structures with limited space, such as zeolite-like complexes, metal complexes, and non-covalent organic framework structures, and using isolated cage structures to study the chemical properties of host and guest. [0003] Extensive achievements have been made in the construction of cage structures based on cations or covalent structures, but few reports have been reported on the assembly of supramolecular systems based on an...

Claims

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Application Information

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IPC IPC(8): C07C273/18C07C275/28C07F1/06C09K11/06G01N21/64
CPCC07C273/1827C07C273/1863C07C273/189C07C275/28C07F1/005C09K11/06G01N21/643C07B2200/13C09K2211/181C09K2211/1007C09K2211/1014
Inventor 杨栋吴彪杨晓娟赵捷
Owner NORTHWEST UNIV
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