Pillar aromatic hydrocarbon and pillar aromatic hydrocarbo-like compound with aggregation-induced emission effect as well as preparation method and application thereof

A technology of aggregation-induced luminescence and column aromatics, which can be applied to non-active ingredients in medical preparations, hydrocarbons, hydrocarbons, etc. glow effect effect

Active Publication Date: 2020-12-15
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Abstract
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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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  • Pillar aromatic hydrocarbon and pillar aromatic hydrocarbo-like compound with aggregation-induced emission effect as well as preparation method and application thereof
  • Pillar aromatic hydrocarbon and pillar aromatic hydrocarbo-like compound with aggregation-induced emission effect as well as preparation method and application thereof
  • Pillar aromatic hydrocarbon and pillar aromatic hydrocarbo-like compound with aggregation-induced emission effect as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] The synthesis of monocyclic quaternary ammonium salt cationic water-soluble column aromatics with aggregation-induced luminescence effect, the synthetic route is as follows:

[0079]

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

Embodiment 2

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

[0089]

[0090] (1) Synthesis of compound A: 1,4-dimethoxybenzene and paraformaldehyde were added to dichloromethane (or chloroform) in a molar ratio of 1:3, and at 0 °C, a catalyst trifluoride was added. The molar ratio of boron ethyl ether, boron trifluoride ethyl ether and 1,4-dimethoxybenzene is 1:1. After 4 hours of reaction at room temperature, add deionized water to quench, extract by liquid separation, dry, and purify by column chromatography to obtain White powdery solid dimethoxy column[5]arene (compound A).

[0091] (2) Synthesis of compound B: in N 2 Under protection, compound A and boron tribromide were added to chloroform in a molar ratio of 1:3, and the reaction was carried out at room temperature for 3 days. Quenched with water, washed, and dried in vacuo to give a white solid dihydroxy column[5]arene (compound B).

[0092] (3...

Embodiment 3

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

[0099]

[0100] Synthesis of compound 5a: Compound 3a, zinc powder and compound 3b were added to tetrahydrofuran in a molar ratio of 1:40:10, and titanium tetrachloride was added at 0 °C, and the molar ratio of compound 3a to titanium tetrachloride was 1:20 It was refluxed overnight, quenched, filtered with suction, extracted by liquid separation, 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 aromatic hydrocarbon and pillar aromatic hydrocarbon-like compound with an aggregation-induced emission effect as well as a preparation method and application thereof.The pillar aromatic hydrocarbon and the pillar aromatic hydrocarbon-like compound have the following structural general formula, or in the structural general formula, R1 is equal to OCH2CH2Br or H; and R2 is equal to OCH2CH2Br or H. The preparation method comprises the following steps: reacting a compound 1 with N-bromo succinimide to obtain a compound 2; then carrying out oxidation reaction to obtain a compound 3, and reacting the compound 3 with benzophenone to obtain the pillar aromatic hydrocarbon and pillar aromatic hydrocarbon-like compound 4 shown in a formula (a); and if the compound 3reacts, obtaining a compound 5 shown as a formula (b). The obtained pillar aromatic hydrocarbon and pillar aromatic hydrocarbon-like compound has an excellent AIE effect, contains a plurality of recognition sites and an electricity-rich cavity, can realize accurate fluorescence regulation and control by utilizing the AIE effect and supramolecular assembly of the pillar aromatic hydrocarbon and pillar aromatic hydrocarbon-like compound, and has wide application in the fields of nano-drug delivery, diagnosis and treatment and the like.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, in particular, to a columnar aromatic hydrocarbon and a columnar aromatic compound having an aggregation-induced luminescence effect with an aggregation-induced luminescence effect, and a preparation method and application thereof. Background technique [0002] Compared with traditional macrocyclic molecules, pillararene has the following characteristics and advantages: First, in terms of synthesis, the synthesis method and derivatization of pillararene The modification is simple; second, the modified column aromatics have good solubility in many different solvents, such as water, methanol, acetone, and dichloromethane, which provides a guarantee for the application of column aromatics in different fields; third , pillar arenes possess rigid and electron-rich cavities that can recognize and bind a variety of guest molecules. In recent years, host-guest chemistry based on pillar...

Claims

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Application Information

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Patent Type & Authority Applications(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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