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Pillararene and pillararene-like compounds with aggregation-induced luminescent effect, preparation method and application thereof

A technology of aggregation-induced luminescence and column aromatics, which is applied to non-active ingredients in medical preparations, hydrocarbons, hydrocarbons, etc. It can solve problems such as not many reports, and achieve improved quantum yield and excellent aggregation induction. effect of glow effect

Active Publication Date: 2022-02-08
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The modification of pillar arenes is usually achieved by using their phenolic hydroxyl groups, but there are few reports on the modification of methylene groups

Method used

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  • Pillararene and pillararene-like compounds with aggregation-induced luminescent effect, preparation method and application thereof
  • Pillararene and pillararene-like compounds with aggregation-induced luminescent effect, preparation method and application thereof
  • Pillararene and pillararene-like compounds with aggregation-induced luminescent effect, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Synthesis of monocyclic quaternary ammonium salt cationic water-soluble pillararene with aggregation-induced luminescent effect, the synthetic route is as follows:

[0079]

[0080] (1) Synthesis of 1,4-bis(2-bromoethoxy)benzene: Add hydroquinone dihydroxy ether and triphenylphosphine to acetonitrile (or acetone) at a molar ratio of 1:3, at 0°C , add carbon tetrabromide in batches (the molar ratio of hydroquinone dihydroxy ether to carbon tetrabromide is 1:3), continue to stir at room temperature for 24h, add deionized water to quench, filter, wash, and column chromatography Separated to obtain a white powdery solid which is 1,4-bis(2-bromoethoxy)benzene. The reaction can also be quenched by adding deionized water, suction filtered and washed with a mixed solution of methanol and water to obtain 1,4-bis(2-bromoethoxy)benzene. Hydrogen spectra such as figure 1 as shown, 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 6.86 (s, 4H), 4.25 (t, J = 6.2Hz, 4H), 3.62 (t, J = 6.2Hz, 4...

Embodiment 2

[0088] Synthesis of monocyclic pillar aromatics with aggregation-induced luminescent effect, the synthetic route is as follows:

[0089]

[0090] (1) Synthesis of compound A: Add 1,4-dimethoxybenzene and paraformaldehyde to dichloromethane (or trichloromethane) at a molar ratio of 1:3, and add catalyst trifluorination at 0°C Boron ether, the molar ratio of boron trifluoride ether to 1,4-dimethoxybenzene is 1:1, react at room temperature for 4 hours, add deionized water to quench, extract by separation, dry, and purify by column chromatography to obtain White powdery solid dimethoxypillar[5]arene (compound A).

[0091] (2) Synthesis of compound B: in N 2 Under protection, compound A and boron tribromide were added to chloroform at a molar ratio of 1:3, and reacted at room temperature for 3 days. It was quenched with water, washed, and dried in vacuo to give dihydroxycylind[5]arene (compound B) as a white solid.

[0092] (3) Synthesis of compound C: in N 2 Under protectio...

Embodiment 3

[0098] Synthesis of monocyclic pillar aromatics with aggregation-induced luminescent effect, the synthetic route is as follows:

[0099]

[0100] Synthesis of compound 5a: Add compound 3a, zinc powder and compound 3b to tetrahydrofuran at a molar ratio of 1:40:10, add titanium tetrachloride at 0°C, and the molar ratio of compound 3a to titanium tetrachloride is 1:20 Refluxed overnight, quenched, suction filtered, separated and extracted, dried, and purified by column chromatography to obtain a white solid (compound 5a).

[0101] The synthesis method of compound 3a is the same as that of Example 1, and the synthesis method of compound 3b is the same as that of Example 2.

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Abstract

The invention provides a pillar arene and pillar arene-like compound with an aggregation-induced luminescence effect, a preparation method and an application thereof. Pillar arenes and pillar arene-like compounds have the following general structural formula: or wherein, R 1 =OCH 2 CH 2 Br or H; R 2 =OCH 2 CH 2 Br or H. The preparation method is as follows: compound 1 is reacted with N-bromosuccinimide to obtain compound 2; then an oxidation reaction occurs to obtain compound 3, and then reacted with benzophenone to obtain columnarene and column-like compounds shown in formula (a) Aromatic compound 4; if compound 3 is reacted by itself to obtain compound 5 shown in formula (b). The pillar arenes and pillar arene-like compounds obtained in the present invention have excellent AIE effects, and contain multiple recognition sites and charge-rich cavities, and can realize precise regulation of fluorescence by using their own AIE effects and supramolecular assembly. There are a wide range of applications in fields such as delivery and diagnostic therapy.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, in particular to pillar arenes and pillar arene-like compounds having aggregation-induced luminescence effects and their preparation methods and applications. Background technique [0002] Pillararenes are a new class of macrocyclic molecules developed in recent years. Compared with traditional macrocyclic molecules, Pillararenes have the following characteristics and advantages: First, in terms of synthesis, the synthesis method and derivatization of Pillararenes The modification is simple; second, the modified pillar aromatics have good solubility in many different solvents, such as water, methanol, acetone, and methylene chloride, which provides a guarantee for the application of pillar aromatics in different fields; third , pillararenes have rigid and electron-rich cavities, which can recognize and bind a variety of guest molecules. In recent years, pillararene-based host-g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/56C07C15/20C07C1/207A61K47/06A61K47/22A61K47/69
CPCC07C15/56C07C15/20A61K47/6949A61K47/22A61K47/06C07C2603/92
Inventor 胡晓玉田雪琪牛蓬勃左旻瓒王开亚
Owner NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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