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Preparation method of near-infrared II region fluorescent small molecules

A near-infrared, small-molecule technology, applied in the field of chemical sensing technology and fluorescence imaging, can solve the problems of cumbersome probe synthesis steps, high requirements for testing instruments, and low fluorescence quantum yield, so as to shorten product preparation time and save Energy consumption and raw material consumption, the effect of high fluorescence quantum yield

Active Publication Date: 2021-10-01
NANJING NUOYUAN MEDICAL DEVICES CO LTD
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Problems solved by technology

[0004] Generally, organic near-infrared second-region fluorescent small molecules are mainly divided into three categories. The first type is a near-infrared second-region fluorescent small molecule with a benzobisthiadiazole structure as the main body. This probe has a high fluorescence quantum yield, but the probe The synthesis steps are cumbersome, and the synthesis requires the use of highly toxic tin reagents
The second type is a near-infrared second-region fluorescent small molecule with polymethyl as the main body. It is mainly an extension of the near-infrared first-region cyanine dye probe and replaces the electron-donating group. lower decomposition, and the quantum yield is lower
The third category is to study cyanine dyes, which have fluorescence tailing at 1000-1200nm, and the fluorescence quantum yield is extremely low, which requires high requirements for testing instruments

Method used

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  • Preparation method of near-infrared II region fluorescent small molecules
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  • Preparation method of near-infrared II region fluorescent small molecules

Examples

Experimental program
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Embodiment 1

[0050] A method for preparing fluorescent small molecules in the second near-infrared region, such as figure 1 shown, including the following steps:

[0051] A, the synthesis of intermediate-M1

[0052] Add 200g of N,N-dimethylformamide, 10g (59.1mmol) of 1,8-naphtholactam, and 0.14g of anhydrous lithium hydroxide in a stirred reactor, and heat up to 125°C under stirring. , replace the air in the reaction system with nitrogen, add 20 g (92.5 mmol) of 1,4-dibromobutane dropwise under the protection of nitrogen, and keep the temperature for 30 to 100 minutes. Then, add 1.2 g of p-toluenesulfonic acid as a stabilizer and continue stirring for 15 After ~60 minutes, rectify under reduced pressure, add ethanol to the bottom liquid of the separation tank, crystallize, filter and dry to obtain 16.2 g (98.50%) of intermediate-M1 in total, and the yield is 92.07%.

[0053] B, the synthesis of naphthalimide salt F1

[0054] Add intermediate M1 (12g, 40mmol) into anhydrous tetrahydrofura...

Embodiment 2

[0067] A method for preparing fluorescent small molecules in the second near-infrared region, comprising the following steps:

[0068] A, the synthesis of intermediate-M1

[0069] Add 200g of N,N-dimethylformamide, 10.2g (59.1mmol) of 1,8-naphtholactam, and 0.14g of anhydrous lithium hydroxide successively into a stirred reactor, heat up to 150 ℃, replace the air in the reaction system with nitrogen, add 20.2g (92.5mmol) of 1,4-dibromobutane dropwise under the protection of nitrogen, keep the temperature for 30-100 minutes, then add 1.2g of stabilizer p-toluenesulfonic acid, continue Stir for 15-60 minutes, rectify under reduced pressure, add ethanol to the bottom liquid of the separation tank, crystallize, filter and dry to obtain 16.08 g (98.32%) of the intermediate product M1 in total, and the yield is 91.32%.

[0070] All the other steps are carried out according to Example 1.

Embodiment 3

[0072] A method for preparing fluorescent small molecules in the second near-infrared region, comprising the following steps:

[0073] A, the synthesis of intermediate-M1

[0074] Add 200g of N,N-dimethylformamide, 10.2g (59.1mmol) of 1,8-naphtholactam, and 0.14g of anhydrous lithium hydroxide to a stirred reactor in sequence, heat up to 138 ℃, replace the air in the reaction system with nitrogen, add 20.2g (92.5mmol) of 1,4-dibromobutane dropwise under the protection of nitrogen, keep the temperature for 30-100 minutes, then add 1.2g of stabilizer p-toluenesulfonic acid, continue Stir for 15-60 minutes, rectify under reduced pressure, add ethanol to the bottom liquid of the separation tank, crystallize, filter and dry to obtain 16.35 g (98.39%) of the intermediate product M1 in total, and the yield is 92.71%.

[0075] All the other steps are carried out according to Example 1.

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Abstract

The invention discloses a preparation method of near-infrared II region fluorescent small molecules, which is used for constructing and preparing fluorescent probe small molecules with a novel structure by using an organic total synthesis method, and belongs to the fields of chemical sensing technology and fluorescence imaging. The near-infrared II region fluorescent small molecules have the advantages of simple synthesis method, easiness in modification, stable structure, high fluorescence quantum yield and the like compared with a fluorescent probe with a benzobithiadiazole structure which is mostly researched at present.

Description

technical field [0001] The invention provides a method for preparing fluorescent small molecules in the second near-infrared region, and relates to the fields of chemical sensing technology and fluorescence imaging. [0002] technical background [0003] Fluorescence microscopy imaging technology is one of the most widely used technologies in current optical imaging technology, and near-infrared fluorescence in vivo imaging technology, which is also fluorescence imaging, is also attracting more and more attention in the field of biomedicine. Traditional fluorescence imaging is mainly concentrated in the near-infrared region (NIR-I), the fluorescence emission wavelength range is 650-950nm, the wavelength is relatively short (<1000nm), and the photon penetration depth is poor, which has become the main obstacle for the application of in vivo biomedical fluorescence imaging . Compared with visible light and NIR-I light, the wavelength is in the range of 1000-1700nm, that is,...

Claims

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Application Information

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IPC IPC(8): C07D495/04C09K11/06
CPCC07D495/04C09K11/06C09K2211/1029C09K2211/1096C09K2211/1007C09B23/0075C09B23/10
Inventor 蔡惠明王毅庆
Owner NANJING NUOYUAN MEDICAL DEVICES CO LTD
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