Photoinduced crystallization isoquinoline salt compound, preparation method and application thereof, and preparation method of nanocrystal

An isoquinoline salt and light-induced technology, applied in the direction of organic chemistry methods, chemical instruments and methods, selection of crystallization auxiliary conditions, etc., can solve the problems of time-consuming and complicated operation, and achieve easy control of size and good biocompatibility The effect of high-efficiency and high-efficiency active oxygen generation ability

Inactive Publication Date: 2020-12-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few simple methods for producing very small crystals with uniform size and good water dispersibility, and the operation is complicated and time-consuming (Adv. Mater., 2017, 29, 1604100)
Therefore, it is very challenging to develop new methods for facile and rapid formation of nanocrystals.

Method used

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  • Photoinduced crystallization isoquinoline salt compound, preparation method and application thereof, and preparation method of nanocrystal
  • Photoinduced crystallization isoquinoline salt compound, preparation method and application thereof, and preparation method of nanocrystal
  • Photoinduced crystallization isoquinoline salt compound, preparation method and application thereof, and preparation method of nanocrystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of the isoquinolinate compound (TIOdB) of light-induced crystallization:

[0046]

[0047] The synthetic route is as follows:

[0048]

[0049] (1) 4,4'-dimethoxy-benzophenone (2.42g, 10mmol), carbon tetrabromide (6.63g, 20mmol) and triphenylphosphine (10.5g, 40mmol) mixture was evacuated and filled with N 2 Three times, and then add 500mL of anhydrous toluene to react at 140°C for 4 days. After cooling to room temperature, the mixture was filtered, washed with dichloromethane, and the filtrate was collected and washed with water. The organic layer was separated and washed with Mg 2 SO 4 Dry and remove solvent by rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether as eluent to afford product 2 as off-white solid in 45% yield.

[0050] (2) Put 1,1-bis(4-methoxyphenyl)-2,2-dibromoethylene (0.67g, 2mmol) into a two-necked flask (250 ml), 4-formylphenylboronic acid (0.31 g, 2.5mmol), Pd(PPh 3 ) ...

Embodiment 2

[0053] The preparation of the isoquinolinate compound (TIOB) of light-induced crystallization:

[0054]

[0055] The synthetic route is as follows:

[0056]

[0057] (1) 4,4'-dimethoxy-benzophenone (2.42g, 10mmol), carbon tetrabromide (6.63g, 20mmol) and triphenylphosphine (10.5g, 40mmol) mixture was evacuated and filled with N 2 Three times, and then add 500mL of anhydrous toluene to react at 140°C for 4 days. After cooling to room temperature, the mixture was filtered, washed with dichloromethane, and the filtrate was collected and washed with water. The organic layer was separated and washed with Mg 2 SO 4 Dry and remove solvent by rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether as eluent to afford product 2 as off-white solid in 45% yield.

[0058] (2) Put 1,1-bis(4-methoxyphenyl)-2,2-dibromoethylene (0.67g, 2mmol) into a two-necked flask (250 ml), 4-formylphenylboronic acid (0.31 g, 2.5mmol), Pd(PPh 3 ) 4...

Embodiment 3

[0061] Preparation of Isoquinolinate Compounds (TABO) Induced by Light Crystallization

[0062]

[0063] The synthetic route is as follows:

[0064]

[0065] (1) The mixture of benzophenone (10mmol), carbon tetrabromide (20mmol) and triphenylphosphine (40mmol) was evacuated and filled with N 2 Three times, and then add 500mL of anhydrous toluene to react at 140°C for 4 days. After cooling to room temperature, the mixture was filtered, washed with dichloromethane, and the filtrate was collected and washed with water. The organic layer was separated and washed with Mg 2 SO 4 Dry and remove solvent by rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether as eluent to afford product 2 as off-white solid in 75% yield.

[0066] (2) Put the product (2mmol) obtained in the previous step into a two-necked flask (250 milliliters), 4-formylphenylboronic acid (2.5mmol), Pd(PPh 3 ) 4 (0.1 mmol), K 2 CO 3(6 mmol) in toluene (60 ...

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Abstract

The invention belongs to the technical field of photoresponse materials, and discloses a photoinduced crystallization isoquinoline salt compound, a preparation method and application thereof, and a preparation method of nanocrystals, and the preparation method of the nanocrystals is a new method for efficient and rapid in-situ preparation of the nanocrystals based on the photoinduced crystallization isoquinoline salt compound. The photo-induced crystallization isoquinoline salt compound has a structure shown as a formula I or a formula II or a formula III or a formula IV, and the structure isdifferent in that isoquinoline salt ionization degrees are different; the photoinduced crystallization isoquinoline salt compound disclosed by the invention realizes photoactivation through a new photophysical mechanism, and the material has the characteristics of AIE, photoactivation and photoinduced crystallization at the same time. The photoactive material disclosed by the invention has the characteristics of illumination intensity dependence, good biocompatibility and mitochondrial targeting, and has a wide application prospect in the fields of photosynthesis illumination intensity optimization and biological imaging and treatment.

Description

technical field [0001] The invention belongs to the technical field of photoresponsive materials, and in particular relates to a light-induced crystallization isoquinolinium salt compound, a preparation method and application thereof, and a preparation method of nanocrystals. Background technique [0002] Light is an important energy source that is non-toxic and harmless, and plays an indispensable role in the development of human civilization. For example, photosynthesis is the uptake of carbon dioxide (CO 2 ) and water (H 2 O) The process of producing organic matter and releasing oxygen, maintaining ecological balance. If there is no light, this balance will be broken, and the survival of human beings will be greatly threatened. Developing more new materials by harnessing light, such as power generation, storage and conversion, has been attracting the attention of many researchers because it can greatly improve our lives. Among them, materials with photoresponsive prop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/04C09K11/06B82Y20/00B82Y40/00B01D9/02
CPCC07D217/04C09K11/06B82Y20/00B82Y40/00B01D9/005C09K2211/1029C07B2200/13B01D2009/0086Y02B20/00
Inventor 唐本忠王志明陈孔麒
Owner SOUTH CHINA UNIV OF TECH
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