CN116082378A - Near infrared seven-membered boron fluoride compound and application thereof - Google Patents

Near infrared seven-membered boron fluoride compound and application thereof Download PDF

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CN116082378A
CN116082378A CN202310026628.8A CN202310026628A CN116082378A CN 116082378 A CN116082378 A CN 116082378A CN 202310026628 A CN202310026628 A CN 202310026628A CN 116082378 A CN116082378 A CN 116082378A
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晏佳莹
王璇
石福茸
张诺诺
王龙
李德江
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China Three Gorges University CTGU
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Abstract

The invention discloses a near infrared seven-element boron fluoride compound and application thereof, wherein the compound is prepared by taking a derivative of seven-element boron fluoride dipyrrole and a para derivative of benzaldehyde as raw materials through piperidine and acetic acid catalytic condensation, and has the advantages of simple synthesis method, convenient separation and purification and higher yield. The viscosity probe can be used for monitoring the viscosity change in a solution, and can also be used as a practical viscosity probe for quantitatively detecting the viscosity values of different areas in cells, so as to detect the microenvironment in the cells, and provide important information for early diagnosis and treatment of some diseases.

Description

Near infrared seven-membered boron fluoride compound and application thereof
Technical Field
The invention relates to a seven-element fluorine boron compound and application thereof, in particular to a near infrared seven-element fluorine boron compound and application thereof, wherein the compound has a certain response to viscosity, and fluorescence is weaker at low viscosity and enhanced along with the increase of viscosity.
Background
Intracellular viscosity controls all diffusion processes including mass transfer, signal transduction, biomolecular interactions, diffusion of metabolites and electron transfer. Viscosity plays a critical role in the production of ATP by mitochondria, and abnormal viscosity may reflect a dysfunctional state, such as abnormal mitochondrial viscosity associated with neurodegenerative diseases, diabetes and cellular malignancies. However, the complex internal environment of an organism results in real-time detection of the viscosity of a living being, which is a challenge. The prior art has the defects of difficult detection, slow detection reaction and the like on the viscosity of living bodies, so that the development of a viscosity probe easy to detect is very important.
The near infrared dye can be applied to imaging of different layers from cells to tissues, and can also be used for visual imaging of the micro-environment viscosity in the zebra fish body. Meanwhile, the near infrared dye can be applied to a liver cirrhosis model, and biological imaging is carried out on liver cirrhosis tissues of mice by inducing the liver cirrhosis of the mice. Experiments have observed that normal liver tissue samples show a weak fluorescence signal, whereas NIR fluorescence signals in liver cirrhosis tissue are significantly enhanced. The above results indicate that the near infrared dye can be successfully applied to viscosity imaging of liver cirrhosis tissues, so that liver cirrhosis liver tissues can be distinguished from normal liver tissues.
The probe provided by the invention is a near infrared seven-element boron fluoride compound responding to viscosity, and the fluorescence of the probe is weak, but the fluorescence is gradually enhanced along with the increase of the viscosity.
Disclosure of Invention
The invention mainly aims to provide a near infrared seven-element fluorine boron compound and application thereof. The technical scheme of the invention is as follows:
a near infrared seven-membered boron fluoride compound and application thereof, wherein the chemical structural formula of the compound is as follows:
Figure BDA0004045323520000021
wherein, the substituent R is any one selected from diphenylamino and cyano. Preferably, the dye has a chemical structural formula:
Figure BDA0004045323520000022
any one of the following.
The synthesis method for synthesizing the near infrared seven-membered boron fluoride compound comprises the following synthesis paths:
Figure BDA0004045323520000031
the method comprises the following steps:
(1) Adding a compound 1 and toluene into a reaction bottle at room temperature, stirring and dissolving, adding para-position derivative of benzaldehyde, piperidine and acetic acid, and heating and refluxing to obtain a reaction solution;
(2) And (3) performing rotary evaporation on the reaction liquid in the step (1), and separating by silica gel column chromatography to obtain a product I.
The compound 1 is a derivative of a seven-membered fluoroborodipyrrole compound, and is condensed with a para-position derivative of benzaldehyde to obtain a compound I; the feeding mole ratio of the compound 1 to the para-position derivative of benzaldehyde is 1:1-10.
The feeding sequence of the step (1) is that the para-position derivative of the compound 1, toluene and benzaldehyde, piperidine, acetic acid, piperidine and acetic acid all play the role of activating reactants and are added finally. The feeding ratio of the compound 1 to the piperidine is 1:1-10; the feeding ratio of the compound 1 to the acetic acid is 1:1-10.
The heating temperature of the step (1) is 30-150 ℃ and the heating time is 2-18 hours. The reaction temperature and time are variable according to the para-substituent of benzaldehyde. When the temperature is raised to above 120 ℃, the yield is reduced; the reaction is difficult to proceed at lower temperatures, e.g., below 60 ℃, resulting in increased reaction times.
The invention has the following beneficial effects:
(1) Some D-a-D structured fluorophores, such as I-2, maintain a moderate dihedral angle between the benzothiadiazole core and the triphenylamine, but the greater steric hindrance of the donor group inhibits intramolecular rotation, thus also limiting sensitivity to viscosity. Taking an N, N-dimethylformamide-glycerin system as an example, the compound has a certain response to the viscosity, the fluorescence of the compound is weak, but the fluorescence gradually increases with the increase of the viscosity, and the maximum fluorescence to the viscosity is enhanced by 6.1 times.
(2) The synthesis reaction condition of the invention is easy to control, the product is simple to purify, and the invention has universal applicability.
(3) The synthesis method has simple synthesis steps and mild reaction conditions.
Drawings
FIG. 1 is a hydrogen spectrum of the compound I-1 obtained in example 1.
FIG. 2 is a hydrogen spectrum of the compound I-2 obtained in example 8.
FIG. 3 is a graph showing fluorescence spectra of the compound I-1 obtained in example 1 in DMF-glycerol mixtures of different proportions.
FIG. 4 shows the fluorescence intensity log I of the compound I-1 obtained in example 1 705nm Linear relationship to log η.
FIG. 5 is a graph showing fluorescence spectra of the compound I-2 obtained in example 8 in DMF-glycerol mixtures of different proportions.
FIG. 6 shows the fluorescence intensity log I of the compound I-2 obtained in example 8 733nm Linear relationship to log η.
Detailed Description
The present invention will be further illustrated by the following examples, but the scope of the invention is not limited to the examples.
Example 1
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 90 ℃ for 8 hours for complete reaction, the reactant is distilled off soon, and black solid I-1 (173.3 mg) is obtained after column chromatography purification, and the yield is 26.5%.
Figure BDA0004045323520000041
Example 2
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (262 mg,2 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 90 ℃ for 8 hours for complete reaction, the reactant is distilled off soon, and the black solid I-1 (312.0 mg) is obtained after column chromatography purification, and the yield is 47.7%. When the amount of 4-cyanobenzaldehyde was increased 1-fold relative to example 1, the yield was increased by 21.2%.
Figure BDA0004045323520000051
Example 3
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.18 mL,2 mmol) and acetic acid (0.12 mL,2 mmol) are sequentially added, the mixture is heated and stirred at 90 ℃ for 8 hours for complete reaction, the reactant is distilled off soon, and black solid I-1 (179.2 mg) is obtained after column chromatography purification, and the yield is 27.4%. When the amounts of piperidine and acetic acid were increased 1-fold relative to example 1, the yields were not significantly changed.
Figure BDA0004045323520000052
Example 4
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 120 ℃ for 6 hours for complete reaction, the reactant is distilled off soon, and black solid I-1 (408.1 mg) is obtained after column chromatography purification, and the yield is 62.4%. When the reaction temperature was increased by 30℃relative to example 1, the reaction time was reduced by 2 hours, and the yield was increased by 35.9%.
Figure BDA0004045323520000061
Example 5
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 140 ℃ for 6 hours for complete reaction, the reactant is distilled off soon, and black solid I-1 (102.7 mg) is obtained after column chromatography purification, and the yield is 15.7%. When the reaction temperature was increased by 50℃relative to example 1, the reaction time was reduced by 2 hours, and the yield was reduced by 10.8%.
Figure BDA0004045323520000062
Example 6
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 60 ℃ for 12 hours for complete reaction, the reactant is distilled off soon, and the black solid I-1 (123.6 mg) is obtained after column chromatography purification, and the yield is 18.9%. When the reaction temperature was reduced by 30℃relative to example 1, the reaction time was increased by 4 hours, and the yield was reduced by 7.6%.
Figure BDA0004045323520000071
Example 7
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 60.00mL of toluene is taken and mixed for dissolution, 4-cyanobenzaldehyde (131 mg,1 mmol), piperidine (0.09 mL,1 mmol) and acetic acid (0.06 mL,1 mmol) are sequentially added, the mixture is heated and stirred at 90 ℃ for 8 hours for complete reaction, the reactant is distilled off soon, and the black solid I-1 (149.8 mg) is obtained after column chromatography purification, and the yield is 22.9%. When the volume of toluene was doubled with respect to example 1, the yield was reduced by 3.6%.
Figure BDA0004045323520000072
Example 8
Seven-membered boron dipyrrole compound (541 mg,1 mmol) of compound 1 is weighed, 30mL of toluene is taken and mixed for dissolution, 4-diphenylaminobenzaldehyde (279 mg,1 mmol) and piperidine (0.09 mL,1 mmol) are sequentially added, acetic acid (0.06 mL,1 mmol) is heated and stirred at 90 ℃ for 8 hours for complete reaction, the reactant is distilled off soon, and the purple solid I-2 (244.4 mg) is obtained after column chromatography purification, and the yield is 30.7%.
Figure BDA0004045323520000081
Example 9 response of Compounds I-1, I-2 to viscosity
Compound I-1 (6.54 mg,0.01 mmol) was weighed and 1mL of DMF was taken and dissolved to prepare a mother liquor of 0.01mol/L, and then 10 μl of each mother liquor was taken and dissolved into a mixture of 3mL of DMF and glycerol of different viscosities, respectively, to prepare a solution to be measured of 33.3 μl/L, wherein (DMF: glycerol=10:0, for example 3mL of DMF, viscosity was 0.77mpa·s), (DMF: glycerol=9:1, for example 2.7mL of DMF and 0.3mL of a compound of glycerol, viscosity was 1.5mpa·s), (DMF: glycerol=8:2, for example 2.4mL of DMF and 0.6mL of glycerol, viscosity was 2.41mpa·s), (DMF: glycerol=7:3, for example 2.1mL of a compound of DMF and 0.9mL of glycerol, viscosity was 4.22mpa·s), (DMF: glycerol=6:4, for example 1.8mL of a compound of DMF and 1.2mL of glycerol, viscosity was 7.36mpa·s), (DMF: glycerol=9:1.7:1, for example 2.7mL of DMF = 2, and (1.7 mL of DMF = 2:2, for example 2.6 mL of DMF) was measured as a fluorescent compound of glycerol, viscosity was measured of 1.4 mL of DMF and viscosity was 1.7 mL of DMF and 0.6mL of glycerol was 1mL of DMF was 1:3 mL, respectively, and viscosity was 1.4 mL of DMF = 2:2, and 0.6mL of glycerol was measured as a fluorescent compound of 2mL of DMF was 1 705nm Linear relationship with log η, resulting in fig. 4.I-1 itself is weak in fluorescence, but as viscosity increases, fluorescence occursThe light gradually increases. The viscosity coefficient was 2.6 and the maximum fluorescence enhancement to viscosity was 9.7 times.
Weighing compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of DME to prepare 0.01mol/L mother solution, dissolving 10 mu L of mother solution into 3mL of a mixture of DME and glycerol with different viscosities respectively to prepare 33.3 mu mol/L solution to be tested, wherein (DME: glycerol=10:0), (DME: glycerol=9:1), (DME: glycerol=8:2), (DME: glycerol=7:3), (DME: glycerol=6:4) (DME: glycerol=5:5), (DME: glycerol=4:6), (DME: glycerol=3:7) and (DME: glycerol=2:8), and respectively detecting fluorescence spectra of the mother solutions, wherein fluorescence gradually increases with the increase of the viscosity. The viscosity can be detected in the range of 0.1-260 mPas.
Weighing compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of DMSO to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of DMSO and glycerol with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (DMSO: glycerol=10:0), (DMSO: glycerol=9:1), (DMSO: glycerol=8:2), (DMSO: glycerol=7:3), (DMSO: glycerol=6:4) (DMSO: glycerol=5:5), (DMSO: glycerol=4:6) and (DMSO: glycerol=3:7), respectively detecting fluorescence spectra of the mother solution, and fluorescence gradually increases with the increase of viscosity. The viscosity range detectable is 0.1-241 mPa.s.
Weighing a compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of ethylene glycol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of ethylene glycol and glycerin with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (ethylene glycol: glycerin=10:0), (ethylene glycol: glycerin=9:1), (ethylene glycol: glycerin=8:2), (ethylene glycol: glycerin=7:3), (ethylene glycol: glycerin=6:4), (ethylene glycol: glycerin=5:5) and (ethylene glycol: glycerin=4:6), respectively detecting fluorescence spectra of the two solutions, and gradually increasing the fluorescence with increasing viscosity. The viscosity range detectable is 0.1-182 mPa.s.
Weighing a compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of ethanol to prepare a mother solution of 0.01mol/L, then respectively dissolving 10 mu L of mother solution into 3mL of a mixture of ethanol and glycerol with different viscosities to prepare a solution to be tested of 33.3 mu mol/L, wherein (ethanol: glycerol=10:0), (ethanol: glycerol=9:1), (ethanol: glycerol=8:2), (ethanol: glycerol=7:3), (ethanol: glycerol=6:4), (ethanol: glycerol=5:5) and (ethanol: glycerol=4:6), respectively detecting fluorescence spectra of the compounds, and gradually increasing fluorescence with the increase of viscosity. The viscosity can be detected in the range of 0.1 to 180 mPas.
Weighing a compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of n-butanol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of n-butanol and glycerin with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (n-butanol: glycerin=10:0), (n-butanol: glycerin=9:1), (n-butanol: glycerin=8:2), (n-butanol: glycerin=7:3), (n-butanol: glycerin=6:4), (n-butanol: glycerin=5:5) and (n-butanol: glycerin=4:6), respectively detecting fluorescence spectra of the n-butanol and glycerin, and gradually increasing fluorescence with increasing viscosity. The viscosity can be detected in the range of 0.1 to 187 mPas.
Weighing a compound I-1 (6.54 mg,0.01 mmol), dissolving 1mL of isopropanol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of a mixture of isopropanol with different viscosities and glycerol to prepare 33.3 mu mol/L solution to be tested, wherein (isopropanol: glycerol=10:0), (isopropanol: glycerol=9:1), (isopropanol: glycerol=8:2), (isopropanol: glycerol=7:3), (isopropanol: glycerol=6:4), (isopropanol: glycerol=5:5) and (isopropanol: glycerol=4:6), respectively detecting fluorescence spectra of the mother solution, and fluorescence gradually increases with increasing viscosity. The viscosity can be detected in the range of 0.1 to 190 mPas.
Compound I-1 (6.54 mg,0.01 mmol) was weighed, 1ml of lpbs was dissolved to prepare a mother solution of 0.01mol/L, then 10 μl of each mother solution was dissolved in 3ml of a mixture of PBS and glycerol of different viscosities, respectively, to prepare a solution to be measured of 33.3 μmol/L, wherein (PBS: glycerol=10:0), (PBS: glycerol=9:1), (PBS: glycerol=8:2), (PBS: glycerol=7:3), (PBS: glycerol=6:4) and (PBS: glycerol=5:5), respectively, their fluorescence spectra were detected, and the fluorescence gradually increased with increasing viscosity. The viscosity can be detected in the range of 0.1 to 150 mPas.
Weighing and combining1mL of DMF was taken for 1-2 (7.96 mg,0.01 mmol) to prepare a mother liquor of 0.01mol/L, and 10. Mu.L of each mother liquor was then respectively dissolved in 3mL of a mixture of DMF and glycerol of different viscosities to prepare a solution to be measured of 33.3. Mu.mol/L (DMF: glycerol = 10:0, e.g., 3mL of DMF, with a viscosity of 0.77 mPa-s), (DMF: glycerol = 9:1, e.g., a compound of 2.7mL of DMF with 0.3mL of glycerol, a viscosity of 1.5 mPa-s), (DMF: glycerol = 8:2, e.g., a compound of 2.4mL of DMF with 0.6mL of glycerol, a viscosity of 2.41 mPa-s), (DMF: glycerol = 7:3, e.g., a compound of 2.1mL of DMF with 0.9mL of glycerol, a viscosity of 4.22 mPa-s), (DMF: glycerol = 6:4, e.g., a compound of 1.8mL of DMF with 1.2mL of glycerol, a viscosity of 7.36 mPa-s) (DMF: glycerol = 5:5, e.g., a compound of 1.5mL of DMF with 1.5mL of glycerol, a viscosity of 14.2 mPa-s), (DMF: glycerol = 4:6, e.g., a compound of 1.2mL of DMF with 1.8mL of glycerol, a viscosity of 19.9 mPa-s), (DMF: glycerol = 6:4, a viscosity of 7:4, e.g., a compound of 0.8 mL of glycerol, a fluorescent intensity of 7.36 mPa-s), (DMF = 6:7:7, e.5 mL of glycerol, a fluorescent intensity of the compound of 1.g., a compound of 7.5 mPa-s, and a fluorescent intensity of the compound of 7.7.36 mPa-s, a fluorescent compound of 7.5 mL of the compound of the glycerol, and a fluorescent compound of the glycerol, measured as shown in the fluorescent compound, respectively, and measured as shown in the fluorescent compound of the fluorescent compound, respectively, 733nm linear relationship with log η, resulting in fig. 6.I-2 itself is less fluorescent, but as the viscosity increases, the fluorescence gradually increases. The viscosity coefficient was 3.46 and the maximum fluorescence enhancement to viscosity was 6.1 times.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of DME to prepare 0.01mol/L mother solution, dissolving 10 mu L of mother solution into 3mL of a mixture of DME and glycerol with different viscosities respectively, and preparing 33.3 mu mol/L of solution to be tested, wherein (DME: glycerol=10:0), (DME: glycerol=9:1), (DME: glycerol=8:2), (DME: glycerol=7:3), (DME: glycerol=6:4) (DME: glycerol=5:5), (DME: glycerol=4:6) and (DME: glycerol=3:7), respectively detecting fluorescence spectra of the compounds, and gradually increasing fluorescence with increasing viscosity. The viscosity can be detected in the range of 0.1 to 250 mPas.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of DMSO to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of DMSO and glycerol with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (DMSO: glycerol=10:0), (DMSO: glycerol=9:1), (DMSO: glycerol=8:2), (DMSO: glycerol=7:3), (DMSO: glycerol=6:4) (DMSO: glycerol=5:5), (DMSO: glycerol=4:6) and (DMSO: glycerol=3:7), respectively detecting fluorescence spectra of the mother solution, and fluorescence gradually increases with the increase of viscosity. The viscosity range detectable is 0.1-241 mPa.s.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of ethylene glycol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of ethylene glycol and glycerin with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (ethylene glycol: glycerin=10:0), (ethylene glycol: glycerin=9:1), (ethylene glycol: glycerin=8:2), (ethylene glycol: glycerin=7:3), (ethylene glycol: glycerin=6:4), (ethylene glycol: glycerin=5:5) and (ethylene glycol: glycerin=4:6), respectively detecting fluorescence spectra of the two solutions, and gradually increasing the fluorescence with increasing viscosity. The viscosity range detectable is 0.1-182 mPa.s.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of ethanol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of ethanol and glycerol with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (ethanol: glycerol=10:0), (ethanol: glycerol=9:1), (ethanol: glycerol=8:2), (ethanol: glycerol=7:3), (ethanol: glycerol=6:4), (ethanol: glycerol=5:5) and (ethanol: glycerol=4:6), respectively detecting fluorescence spectra of the compound, and gradually increasing fluorescence with the increase of viscosity. The viscosity can be detected in the range of 0.1 to 180 mPas.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of n-butanol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of n-butanol and glycerin with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (n-butanol: glycerin=10:0), (n-butanol: glycerin=9:1), (n-butanol: glycerin=8:2), (n-butanol: glycerin=7:3), (n-butanol: glycerin=6:4), (n-butanol: glycerin=5:5) and (n-butanol: glycerin=4:6), respectively detecting fluorescence spectra of the n-butanol and glycerin with increasing viscosity. The viscosity can be detected in the range of 0.1 to 187 mPas.
Weighing compound I-2 (7.96 mg,0.01 mmol), dissolving 1mL of isopropanol to prepare 0.01mol/L mother solution, then respectively dissolving 10 mu L of mother solution into 3mL of mixture of isopropanol and glycerol with different viscosities to prepare 33.3 mu mol/L solution to be tested, wherein (isopropanol: glycerol=10:0), (isopropanol: glycerol=9:1), (isopropanol: glycerol=8:2), (isopropanol: glycerol=7:3), (isopropanol: glycerol=6:4), (isopropanol: glycerol=5:5), (isopropanol: glycerol=4:6) and (isopropanol: glycerol=3:7), respectively detecting fluorescence spectra of the mother solutions, and gradually increasing fluorescence with the increase of viscosity. The viscosity range detectable is 0.1-205 mPas.
Compound I-2 (7.96 mg,0.01 mmol) was weighed, 1ml of lpbs was dissolved to prepare a mother solution of 0.01mol/L, then 10 μl of each mother solution was dissolved in 3ml of a mixture of PBS and glycerol of different viscosities, respectively, to prepare a solution to be measured of 33.3 μmol/L, wherein (PBS: glycerol=10:0), (PBS: glycerol=9:1), (PBS: glycerol=8:2), (PBS: glycerol=7:3), (PBS: glycerol=6:4) and (PBS: glycerol=5:5), respectively, their fluorescence spectra were detected, and the fluorescence gradually increased with increasing viscosity. The viscosity can be detected in the range of 0.1 to 150 mPas.
The foregoing embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the present invention, and the embodiments and features of the embodiments in the present application may be arbitrarily combined with each other without collision. The protection scope of the present invention is defined by the claims, and the protection scope includes equivalent alternatives to the technical features of the claims. I.e., equivalent replacement modifications within the scope of this invention are also within the scope of the invention.

Claims (9)

1. A near infrared seven-membered boron fluoride compound, which is characterized by having the chemical structural formula:
Figure FDA0004045323510000011
wherein the substituent R is selected from diphenylamino or cyano.
2. The method for synthesizing the near infrared seven-membered boron fluoride compound according to claim 1, characterized in that the method comprises the following synthetic routes:
(1) Adding a compound 1 and toluene into a reaction bottle at room temperature, stirring and dissolving, adding para-derivative of benzaldehyde, piperidine and acetic acid, and heating and refluxing for reaction to obtain a reaction solution;
(2) And (3) performing rotary evaporation on the reaction liquid in the step (1), and separating by silica gel column chromatography to obtain a product I.
3. The method according to claim 2, wherein in the step (1), the molar ratio of the compound 1 to the para-position derivative of benzaldehyde is 1:1-10.
4. The method according to claim 2, wherein the step (1) is carried out in the order of compound 1, toluene, para-derivative of benzaldehyde, piperidine, acetic acid; the feeding ratio of the compound 1 to the piperidine to the acetic acid is 1:1-10:1-10.
5. The method according to claim 2, wherein the para-derivative of benzaldehyde is 4-cyanobenzaldehyde or 4-diphenylaminobenzaldehyde.
6. The method according to claim 2, wherein the heating reflux temperature of step (1) is 30 to 150 ℃ and the reaction time is 2 to 18 hours.
7. Use of the near infrared seven-membered boron fluoride compound of claim 1 for detecting viscosity in an organic solution.
8. The use of claim 7, wherein the organic solution comprises one or more of glycerol, DMF, DME, DMSO, ethylene glycol, ethanol, n-butanol, isopropanol, PBS.
9. The use according to claim 7, wherein the viscosity detection range is 0.1-300 mpa.s.
CN202310026628.8A 2023-01-09 2023-01-09 Near infrared seven-membered boron fluoride compound and application thereof Pending CN116082378A (en)

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