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Near-infrared fluorescent molecule with double (multi) photon excitation and synthesis method of near-infrared fluorescent molecule

A compound, selected technology, applied in material excitation analysis, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of limited spatial resolution, poor soft tissue contrast, etc., achieve small scattering coefficient, strong penetrating ability, low The effect of autofluorescence

Pending Publication Date: 2021-10-26
CIXI INST OF BIOMEDICAL ENG NINGBO INST OF MATERIALS TECH & ENG CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented method allows for introducing certain atoms into organic chemical structures called naphthaquinones (a type of substance). These atomic groups make up different parts of these structure - they help absorb specific types of electromagnetic waves better than other ones like X rays. By doing this, researchers may use them to study how cells function properly when exposed to radiation from various sources such as xray tubes, gamma rays, radioactive particles, etc., potentially improving their effectiveness in medical applications.

Problems solved by technology

This patents discuss different types of technology for improving image quality during medical procedures or treatments like surgery. However, traditional methods may result in better visual results at specific areas where there was no clear difference between them. Fluorescein angiogram can provide detailed images that highlight blood vessels without making everything look grayish white compared to other diagnostic tools.

Method used

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  • Near-infrared fluorescent molecule with double (multi) photon excitation and synthesis method of near-infrared fluorescent molecule
  • Near-infrared fluorescent molecule with double (multi) photon excitation and synthesis method of near-infrared fluorescent molecule
  • Near-infrared fluorescent molecule with double (multi) photon excitation and synthesis method of near-infrared fluorescent molecule

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Experimental program
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Effect test

Embodiment 1

[0112] This embodiment synthesizes compound 1 according to the following route:

[0113]

[0114] (1) Synthesis of compound 5a

[0115] 4-(diphenylamino)phenylboronic acid, 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole, potassium carbonate, tetrakis(triphenylphosphine) Add dioxane and water to palladium in a molar ratio of 1:2.5:10:0.04, the volume ratio of dioxane and water is 4:1, under the protection of an inert gas, heat and reflux for 12h, and purify to obtain compound 5a, producing rate 56%.

[0116] (2) Synthesis of compound 6a

[0117] Compound 5a and iron powder were dissolved in acetic acid at a molar ratio of 1:12. The amount of acetic acid added was sufficient to dissolve the raw materials. The reaction was carried out at 100 degrees Celsius for 5 hours for purification to obtain compound 6a with a yield of 93%.

[0118] (3) Synthesis of compound 1

[0119] Dissolve compound 6a and selenium dioxide in dichloromethane at a molar ratio of 1:2.5, the amount ...

Embodiment 2

[0123] This embodiment synthesizes compound 31 according to the following route:

[0124]

[0125] (1) Synthesis of compound 1

[0126] Compound 6a and benzil were dissolved in acetic acid and chloroform at a molar ratio of 1:1.2, the solvent volume ratio was 1:1, and purified at 60°C for 8 hours to obtain compound 31 with a yield of 90%.

[0127] image 3 It is the emission spectrum of compound 31 under two-photon excitation. In the figure, curve 1 represents that the emission wavelength is about 500nm and 750nm when the excitation wavelength is 1000nm; curve 2 represents that the emission wavelength is about 750nm when the excitation wavelength is 1100nm; curve 3 represents that the emission wavelength is about 750nm when the excitation wavelength is 1200nm Its emission wavelength is about 750nm when curve 4 represents excitation wavelength is 1300nm; Its emission wavelength is approximately 750nm when curve 5 represents excitation wavelength is 1400nm; Its emission wav...

Embodiment 3

[0129] This embodiment synthesizes compound 45 according to the following route:

[0130]

[0131] (1) Synthesis of Compound 43

[0132] Add compound 41, compound 42, potassium carbonate, tetrakis(triphenylphosphine) palladium in a molar ratio of 1:5:20:0.08 to dioxane and water, and the volume ratio of dioxane to water is 8:1, Under the protection of nitrogen, it was heated to reflux for 24 h for purification to obtain compound 43.

[0133] (2) Synthesis of compound 44

[0134] Dissolve compound 43 and iron powder in acetic acid at a molar ratio of 1:12, the amount of acetic acid added can dissolve the raw materials, react at 100 degrees Celsius for 12 hours for purification, and compound 44 is obtained.

[0135] (3) Synthesis of compound 45

[0136] Dissolve compound 44 and selenium dioxide in dichloromethane at a molar ratio of 1:4, the amount of dichloromethane can dissolve the raw material, react at room temperature for 8 hours for purification, and obtain compound ...

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PUM

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Abstract

The invention discloses a compound, and a preparation method and application thereof. The compound has a chemical formula as shown in the specification. In the formula, R<1> is selected from one of S, Se and Te; R<2> is selected from one of Se, Te and a group with the formula shown in the specification; R<3> is selected from one of groups with the chemical formula shown in a formula (1); and R<4> is selected from one of a group with a chemical formula shown in a formula (2) and R<5>. The formula (1) is shown in the specification, m and n are independently selected from 0 or 1, and m and n are not 0 at the same time; the formula (2) is shown in the specification, and R<6> is selected from H or R<5>; and R<5> is Ph and phenyl. The compound is simple in preparation method, has a large absorption wavelength and a large fluorescence emission wavelength, can reach a near-infrared second region, and has a wide application prospect in the aspect of biological imaging. The invention provides a near-infrared fluorescent molecule with double (multi) photon excitation, and a synthesis method thereof.

Description

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Claims

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Application Information

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Owner CIXI INST OF BIOMEDICAL ENG NINGBO INST OF MATERIALS TECH & ENG CHINESE ACAD OF SCI
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