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Near-infrared photo-thermal dye based on aza-fluoro borane, preparation and application

A near-infrared light, heterofluoroborane technology, applied in the direction of azo dyes, luminescent materials, organic dyes, etc., to achieve the effect of weakening damage, good photothermal performance, and deep tissue penetration depth

Inactive Publication Date: 2017-12-22
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Azafluoroborane dyes are generally used in the fields of biomarkers, imaging, photodynamic therapy, etc. So far, few people have reported the use of effective theoretical guidance to design and synthesize azafluoroborane dyes with good photothermal effects

Method used

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  • Near-infrared photo-thermal dye based on aza-fluoro borane, preparation and application
  • Near-infrared photo-thermal dye based on aza-fluoro borane, preparation and application
  • Near-infrared photo-thermal dye based on aza-fluoro borane, preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of Azafluoroborane Photothermal Dye C

[0036]

[0037] Synthesis of Compound 2

[0038] Take a clean two-necked bottle, add magneton, 1.49g of p-dimethylaminobenzaldehyde (about 10mmol), 2.8g of 1 (about 10mmol) and 40ml of ethanol solution. After stirring until all the solids were dissolved, slowly add 23ml of sodium hydride solution (containing 2.0g of sodium hydroxide). The reaction was stirred at room temperature for 24 h, and a yellow solid was precipitated during the reaction. After the reaction, 1M hydrochloric acid solution was used to adjust the reaction solution to neutrality, and a solid was obtained by suction filtration, and washed three times with deionized water. 2.1 g of a pale yellow solid were dried in vacuo.

[0039] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) = 8.01 (d, J = 8.0Hz, 2H), 7.78 (d, J = 16.0Hz, 1H), 7.53 (d, J = 8.0Hz, 2H), 7.35 (d, J = 16.0 Hz,1H),6.98(d,J=8.0Hz,2H),6.69(d,J=8.0Hz,2H),4.21(t,2H),3.89(t,2H),3.77-3.65...

Embodiment 2

[0049] Example 2: Synthesis of Azafluoroborane Photothermal Dye D

[0050]

[0051] Synthesis of compound 1

[0052] Take a clean two-necked bottle, add magneton, 1.36g of p-hydroxyacetophenone (about 10mmol), 9.66g of bromooctane (about 50mmol), 6.91g of potassium carbonate and 40ml of anhydrous N,N-dimethyl formamide solution. Under magnetic stirring, react at 80°C for 24h. After the reaction was completed, water / dichloromethane was extracted several times, and the organic phases were combined. After separation by chromatography column, 2.46 g of light yellow liquid was obtained (the yield was about 99%).

[0053] Synthesis of Compound 2

[0054] Take a clean two-necked bottle, add magneton, 1.24g of 1 (about 5mmol), 0.75g of p-dimethylaminobenzaldehyde (about 5mmol) and 20ml of ethanol solution. Stir until all the solids are dissolved, then slowly add 5ml of sodium hydride solution (containing 1.00g of sodium hydroxide). The reaction was stirred at room temperature...

Embodiment 3

[0067] Embodiment 3: the test of the molecular weight of C

[0068] Take a small amount of sample C, mix it with the matrix, then apply the sample, and measure it with MALDI-TOF / TOF, as shown in Figure 1, which preliminarily proves the correctness of the C molecule.

[0069] [m / e] (M, MALDI-TOF) theoretical value: 907.85, experimental value: 907.46

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Abstract

The invention discloses a near-infrared photo-thermal dye based on aza-fluoro borane, preparation and application. The photo-thermal dye comprises an electron-donating group containing lone pair electrons and a basic aza-fluoro borane skeleton. The near-infrared photo-thermal dye based on aza-fluoro borane is prepared through steps as follows: (1), ketene synthesis: ketene is prepared from aldehyde ketone by an addition-elimination reaction under the alkaline condition; (2), an addition reaction of ketene and nitromethane; (3), a cyclization reaction; (4), a coordination reaction: a product obtained in the step (3) coordinates with boron difluoride, and a target product is obtained. The photo-thermal dye can be applied to the technical fields of photodynamic therapy and photo-thermal therapy under the guidance of photo-thermal imaging and photo-acoustic imaging, bio-marker and detection and the like.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. In particular, it relates to a photothermal dye with near-infrared absorption based on azafluoroborane, a preparation method thereof and its application in the fields of fluorescence imaging, photothermal imaging, photoacoustic imaging, photothermal therapy and the like. Background technique [0002] Tumors threaten human health. Traditional tumor treatment methods, such as surgery, chemotherapy, and radiotherapy, have some problems and are often accompanied by side effects. As a non-invasive tumor treatment method, photothermal therapy can precisely treat tumor sites in real time. Greatly improved the effect of tumor treatment. The choice of photothermal materials plays a decisive role in the effect of photothermal therapy. Therefore, how to choose an ideal photothermal material has attracted widespread attention. [0003] In recent years, some main luminophores, suc...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00A61K49/22A61K49/00A61K41/00A61P35/00
CPCC07F5/022A61K41/0052A61K49/0021A61K49/22C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1085
Inventor 赵强黄维徐云剑刘淑娟赵梦龙冯腾
Owner NANJING UNIV OF POSTS & TELECOMM
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