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Near-infrared chlorinated aza-boron fluoride dye, and preparation method and application of dye

A technology of heterofluoroborane and nitrogen chloride is applied in the field of organic optoelectronic materials to achieve the effects of weakening the influence of detection signals, simple preparation, separation and purification processes, and abundant raw material sources.

Inactive Publication Date: 2018-09-07
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Azafluoroborane dyes are generally used in biomarkers, imaging, photodynamic therapy and other fields. So far, there are few reports on how to balance their photothermal and photodynamic effects to achieve the best energy utilization efficiency. Therefore, it is necessary to Design and synthesize near-infrared dyes with good photothermal and photodynamic synergistic effects to solve the shortcomings of existing technologies

Method used

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  • Near-infrared chlorinated aza-boron fluoride dye, and preparation method and application of dye
  • Near-infrared chlorinated aza-boron fluoride dye, and preparation method and application of dye
  • Near-infrared chlorinated aza-boron fluoride dye, and preparation method and application of dye

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of chlorine atom substituted azafluoroborane, the concrete synthetic route is as follows:

[0033]

[0034] Synthesis of Compound 1

[0035] Take a clean two-necked bottle, add magnetron, 3.40g of p-hydroxyacetophenone (about 25mmol), 24.14g of bromooctane (about 125mmol), 17.25g of potassium carbonate and 20mL of anhydrous N,N-dimethyl formamide solution. Under magnetic stirring, the reaction was carried out at 80°C for 24 hours. After the reaction, the mixture was extracted with water / dichloromethane for several times, and the organic phases were combined. Chromatographic column separation gave a colorless liquid (99% yield).

[0036] Synthesis of Compound 2

[0037] Take a clean two-necked bottle, add magnetron, 3.05g of p-hydroxybenzaldehyde (about 25mmol), 24.14g of bromooctane (about 125mmol), 17.25g of potassium carbonate and 20mL of anhydrous N,N-dimethylformamide solution. Under magnetic stirring, the reaction was carried ou...

Embodiment 2

[0052] Example 2: Measurement of the molecular weight of compound 7

[0053] Take a small amount of compound 6, mix it with the matrix, and then spot the sample and measure it with MALDI-TOF. The results are as follows figure 1 , which preliminarily proved the correctness of compound 7 molecule.

[0054] [m / e](M, MALDI-TOF) theoretical value: 1077.59, experimental value: 1078.12.

Embodiment 3

[0055] Example 3: NMR test of compound 7

[0056] Dissolve 0.5 mg of compound 7 in 0.5 mL of deuterated chloroform, and through nuclear magnetic test, the results are as follows figure 2 , which further proved the correctness of compound 7 molecule.

[0057] 1 H NMR (400MHz, CDCl 3 )d(ppm): δ7.97–7.90(m,4H),7.81–7.75(m,4H),7.01–6.93(m,8H),4.05–3.99(m,8H),1.87–1.76(m, 8H), 1.53–1.42 (m, 8H), 1.40–1.25 (m, 32H), 0.92–0.88 (m, 12H).

[0058] 13 C NMR (100MHz, CDCl 3 )d(ppm): δ161.32, 160.39, 155.60, 143.21, 138.92, 132.35, 122.83, 120.96, 114.16, 68.11, 31.85, 29.55, 29.10, 26.08, 22.69.

[0059] 19 F NMR (376.5MHz, CDCl 3 ):d(ppm):δ-131.51(q,2F).MALDI-TOF-MS(m / z):calcdfor C 64 H 84 BCl 2 F 2 N 3 O 4 , 1079.10; found, 1077.47.

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Abstract

The invention discloses a near-infrared chlorinated aza-boron fluoride dye. In a preparation process of the dye, a chlorine substituted basic aza-boron fluoride framework is finally prepared by a multi-step reaction such as a synthesis-addition reaction-cyclic reaction-coordination substitution reaction of ketene. The dye has stronger absorption and emission in a near-infrared wavelength area; a photo-thermal property and chemical stability are improved; and the dye can be used for the fields of photodynamic treatment and photo-thermal treatment under guidance of photo-thermal imaging and photoacoustic imaging, bio-labeling and detection, a time gate imaging technology and the like.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials. Specifically, it relates to an azafluoroborane-based photothermal dye with near-infrared absorption, a preparation method thereof, and its application in the fields of fluorescence imaging, photothermal imaging, photoacoustic imaging, photothermal therapy, and photodynamic therapy. Background technique [0002] Tumor has always been a lethal disease that is difficult to overcome, and the current treatment methods for tumors still remain in traditional surgery, chemotherapy or radiotherapy; these treatment methods are often accompanied by toxic side effects, and the treatment effect is not good. Exploring new treatment methods with less toxic and side effects, or adding some auxiliary means on the basis of existing treatment methods, thereby improving curative effect and reducing toxic and side effects, is an urgent problem to be solved in current tumor treatment. [0003...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B57/00A61K41/00A61K49/00A61K49/22A61P35/00
CPCA61K41/0052A61K41/0057A61K49/0021A61K49/22A61P35/00C07F5/022C09B57/00
Inventor 刘淑娟赵强吴立才赵梦龙黄维杨天赦徐云剑
Owner NANJING UNIV OF POSTS & TELECOMM
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