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Anthryl macrocyclic molecule as well as preparation method and application thereof

A macrocyclic molecule, anthracenyl technology, applied in the field of anthracenyl macrocyclic molecules and its preparation, can solve the problems of lack of fluorescence properties, weakened non-covalent weak interaction strength between molecules, limited driving force, etc.

Pending Publication Date: 2021-12-28
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Macrocyclic molecules are widely used in molecular recognition. Traditional macrocyclic host compounds such as cyclodextrins, calixarenes, cucurbiturils, and pillararenes can carry out molecular recognition in the aqueous phase due to the drive of hydrophobic effects, but due to the hydrophobic The driving force that the effect can provide is limited, and these traditional macrocyclic molecules are difficult to meet the recognition and application requirements in complex environments
With the development of organic synthesis technology, people have also developed some new macrocyclic molecules, but there are still the following problems: (1) The recognition strength of the object in water is usually not high, especially it is difficult to recognize the electroneutral molecule with high strength. Hydrophilic molecules and electrically neutral polar functional groups; (2) groups that usually lack fluorescent properties can only be bonded to guest molecules, and cannot be detected by optical methods; (3) due to The essence of intermolecular non-covalent bonds (such as hydrogen bonds) is electrostatic force, which is inversely proportional to the dielectric constant of the environment. Solvents with large dielectric constants (such as water) will weaken the weak interactions between intermolecular non-covalent bonds Therefore, it is difficult to use intermolecular non-covalent bonds to drive molecular recognition in solvents with large dielectric constants

Method used

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  • Anthryl macrocyclic molecule as well as preparation method and application thereof
  • Anthryl macrocyclic molecule as well as preparation method and application thereof
  • Anthryl macrocyclic molecule as well as preparation method and application thereof

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preparation example Construction

[0047] Another aspect of the present invention also provides the preparation method of the aforementioned anthracenyl macrocyclic molecule, which comprises the following steps:

[0048] Provide the rigid bridged bisanthracene shown in formula II-1, make it undergo acylation reaction, prepare the bisaldehyde group rigid bridged bisanthracene shown in formula III-1; the bisaldehyde shown in formula III-1 Rigid bridging bisanthracene undergoes an amination reaction to prepare a compound shown in formula IV-1;

[0049] Provide the rigid bridged bisanthracene shown in formula II-2, make it undergo acylation reaction, prepare the bisaldehyde group rigid bridged bisanthracene shown in formula III-2; the bisaldehyde shown in formula III-2 The base rigid bridging bisanthracene is through oxidation reaction, prepares the compound shown in formula IV-2;

[0050]

[0051] Carrying out cyclization reaction of compounds shown in IV-1 and IV-2 to prepare anthracenyl macrocyclic molecules...

Embodiment 1

[0077] (1) Preparation of bisaldehyde group rigid bridged bisanthracene compound A:

[0078]

[0079] Intermediate Compound S 0 Preparation: Dissolve 9-bromoanthracene (12g, 45mmol) in dry tetrahydrofuran (300mL), add n-butyl lithium in dry tetrahydrofuran (2.60M, 19.2mL, 50.6mmol ). After maintaining -80°C and stirring for two hours, zinc chloride (9.1 g, 66.7 mmol) was added. Maintain -80°C, stir for four hours, then warm up to room temperature, and stir for one day. 1,3-Dibromo-4,6-dimethoxybenzene (3.4g, 11.5mmol), bis(cyanobenzene)palladium dichloride (0.44g, 1.2mmol) and tri-tert-butylphosphine in n-hexyl Add alkane solution (10%wt, 5.6mL, 2.3mmol) into 50mL dry THF, and stir at room temperature for half an hour under nitrogen protection. The solution was transferred and injected into the reaction system which had been stirred at room temperature for one day, and then the temperature was raised to 85° C. and stirred for two days. Afterwards, the reaction was cool...

Embodiment 2

[0091] (1) Preparation of bisaldehyde group rigid bridged bisanthracene compound B:

[0092]

[0093] Synthetic intermediate product S 1 : Compound S 0 (2.4g, 5.0mmol) was dissolved in 50mL of dichloromethane, BBr was added at 0°C 3 (5.0 mL, 50.0 mmol). After stirring at 0°C for half an hour, the mixture was warmed up to room temperature and stirred for four hours. Pour the reaction solution into an ice-water bath, adjust the pH to 5-6 with NaOH solution, and extract with dichloromethane (50 mL×3) and ethyl acetate (50 mL×3). The organic phases were combined, and the organic solvent was removed under reduced pressure to obtain the solid product S 1 (2.9g, 90%).

[0094] The preparation of compound B: intermediate product S 1 (6.3g, 10.0mmol) was dissolved in 200mL of dichloromethane, and 1,1-dichloromethyl ether (3.6mL, 40.0mmol) was added. The temperature was lowered to 0°C, and TiCl was added dropwise under stirring 4 (4.0 mL, 40.0 mmol). Continue to maintain 0° C...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to an anthryl macrocyclic molecule as well as a preparation method and application thereof. The invention provides an anthryl macrocyclic molecule with a structure as shown in a formula I. The anthryl macrocyclic molecule has a deep cavity structure, a hydrogen bond bonding site is arranged in a cavity, and a hydrogen bond is shielded in a relatively non-polar deep cavity environment, so that on one hand, the strength of the hydrogen bond is slightly weakened; on the other hand, competition of water molecules to the hydrogen bonding site is avoided. Therefore, the anthryl macrocyclic molecule provided by the invention can be used for identifying the molecule to be detected by simultaneously utilizing the hydrophobic effect and the hydrogen bond, so that the bonding ability to the guest molecule is greatly improved. Besides, due to the introduction of anthryl which is a large conjugated system, macrocyclic molecules have certain light absorption capability, and a foundation is laid for realizing detection and sensing of chiral molecules through an optical method. Therefore, the macrocyclic molecule provided by the invention has a wide application prospect in the field of molecular recognition.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an anthracene-based macrocyclic molecule and its preparation method and application. Background technique [0002] Molecular recognition is the process of bonding between host molecules and guest molecules. Molecular recognition, especially water-phase molecular recognition, is very common in biological systems and is the basis of life phenomena. The study of molecular recognition in aqueous phase not only helps to understand the recognition process in life activities, but also provides a basis for the design and synthesis of artificial functional molecular recognition systems. [0003] Macrocyclic molecules are widely used in molecular recognition. Traditional macrocyclic host compounds such as cyclodextrins, calixarenes, cucurbiturils, and pillararenes can carry out molecular recognition in the aqueous phase due to the drive of hydrophobic effects, but due to the hyd...

Claims

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Application Information

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IPC IPC(8): C07D245/04G01N21/19
CPCC07D245/04G01N21/19C07B2200/09
Inventor 蒋伟庞新语周航
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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