Near-infrared dye and preparation method thereof

A technology of red light and dyes, which is applied in the field of near-red dyes and their preparation, and can solve the problems of limited application

Active Publication Date: 2016-05-25
德州虹桥染料化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Yet, also have drawback for most BODIPY compounds, the ultraviolet absorption of many compounds is less than 600nm, limits its application (Hoyer, P.; Staudt, T.; Engelhardt, J.; Hell, S.W.QuantumDotBlueingandBlinkingEnablesFluorescenceNanoscopy.NanoLett. ,2011,11,245-250), therefore, it is a challenge to develop new fluorescent dyes with absorption wavelength greater than 600nm

Method used

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  • Near-infrared dye and preparation method thereof
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  • Near-infrared dye and preparation method thereof

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Experimental program
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Embodiment 11

[0019] Embodiment 1.1 (preferred embodiment)

[0020] Compound 1,7-Dimethyl-3,5-(bis(4-methoxyphenyl-2-enyl))-8-(2-(1,2,3-trihydroisoquinoline)) -4-boron-3a,4a-dipyrrole (abbreviated as BODIPY-DPD)

[0021] BODIPY-C (1.03mmol) and 1,2,3,4-tetrahydroisoquinoline (1.545mmol) were mixed at a molar ratio of 1:1.5, then 25mL of tetrahydrofuran was added, followed by K 2 CO 3 (1.236mmol), KI (34.2mg, 0.206mmol) and hexadecylcrown ether (0.1mg); they were mixed and heated to 65°C in a water bath for 6 hours, the reaction solution was concentrated and dissolved in 10mL of dichloromethane and filtered, and the solution was set up The water trap was refluxed, followed by adding 4-methoxybenzaldehyde (2.575 mmol), adding 20 mL of toluene, followed by adding 4-methylbenzenesulfonic acid and piperidine, 4-methylbenzenesulfonic acid (0.206 mmol) and piperidine The ratio of (0.515mmol) to BODIPY-C is 0.2:1 and 0.5:1 respectively. After mixing, heat to 120°C and react for 8 hours. Saturat...

Embodiment 12

[0022] Embodiment 1.2 (preferred embodiment)

[0023] BODIPY-C (1.03mmol) and ethyl 5-hydroxyisophthalate (1.545mmol) were mixed at a molar ratio of 1:1.5, then 25mL of tetrahydrofuran was added, followed by K 2 CO 3 (1.236mmol) KI (0.206mmol) hexadecyl crown ether (0.1mg); where mixed and heated to 65°C in a water bath for 6 hours. Concentrate the reaction solution and dissolve it with 10ml of dichloromethane, then filter the solution to set up a water trap to reflux, then add 4-methoxybenzaldehyde (351.2mg, 2.575mmol), add 20mL of toluene, then add 4-methylbenzenesulfonic acid and piperazine The ratios of pyridine, 4-methylbenzenesulfonic acid (0.206mmol) and piperidine (0.515mmol) to BODIPY-C are 0.2:1 and 0.5:1 respectively. After mixing, heat to 140°C and react for 8 hours. After the reaction , concentrated the reaction liquid, added 20mL of dichloromethane, extracted and washed with 3×30mL saturated brine, extracted the aqueous phase with 3×20mL of dichloromethane, com...

Embodiment 21

[0026] BODIPY-C (1.03mmol) and 1,2,3,4-tetrahydroisoquinoline (0.515mmol) were mixed at a molar ratio of 2:1, then 25mL of tetrahydrofuran was added, followed by K 2 CO 3 (1.236mmol) KI (34.2mg, 0.206mmol) hexadecylcrown ether (0.1mg); the mixture was heated to 65°C in a water bath for 6 hours, the reaction solution was concentrated and dissolved in 10mL of dichloromethane and then filtered, and the solution was set up to divide the water Then add 4-methoxybenzaldehyde (2.575mmol), add 20mL toluene, then add 4-methylbenzenesulfonic acid and piperidine, 4-methylbenzenesulfonic acid (0.206mmol) and piperidine (0.515 The ratio of mmol) to BODIPY-C is 0.2:1 and 0.5:1 respectively. After mixing, heat to 120°C and react for 8 hours. After the reaction, concentrate the reaction solution, add 20mL of dichloromethane, and use 3×30mL saturated brine After extraction and washing, the aqueous phase was extracted with 3×20 mL of dichloromethane, the organic phases were combined, dried ove...

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Abstract

The invention relates to two novel difluoro boron dipyrromethene compounds which can be used as near-infrared fluorescent dyes and a preparation method thereof and belongs to the techcnial field of fluorescent probes. 8-(4-(chloromethyl) phenyl)-4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole (labeled as BODIPY-C), 1,2,3,4-tetrahydro naphthalene, 5-hydroxyl isophthalate and p-anisaldehyde are used as raw materials to synthesize the two novel difluoro boron dipyrromethene (BODIPY) derivatives. The two compounds are compounds for near-infrared absorption and near-infrared fluorescence emission and can be expected to be used as fluorescent probes for imaging in cells or organisms, and background interference is reduced.

Description

technical field [0001] The invention relates to two new difluoroboron-dipyrromethene compounds and a preparation method thereof, which can be used as near-infrared fluorescent dyes and belong to the technical field of fluorescent probes. Specifically, these two compounds have better absorption and absorption properties in the near-infrared region. Near-infrared emission can be used as a new type of near-infrared dual-function imaging agent. Background technique [0002] Difluoroborondipyrrole (BODIPY) compounds have relatively strong ultraviolet absorption and high fluorescence quantum yield, and can change its ultraviolet absorption and fluorescence properties by chemical modification on the structure. In addition, compared with traditional near-infrared Compared with organic dyes (such as rhodamine B), this type of compound has high photostability and is not prone to photolysis, so it is widely used in the labeling of proteins and DNA [Metzker, M.L.; .; Yee, M.-C.; Fas, S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10C09K11/06A61K49/00G01N21/33G01N21/64
CPCA61K49/0021C09B23/0091C09B23/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096G01N21/33G01N21/64
Inventor 陈秋云兰亚泉
Owner 德州虹桥染料化工有限公司
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