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Near-infrared two-region fluorescent molecule containing benzobithiadiazole and preparation method thereof, fluorescent nano-particles and preparation method and application thereof

A benzobisthiadiazole and fluorescent nanoparticle technology, which is applied in the field of fluorescent materials, can solve the problems of low fluorescence stability, poor biocompatibility of organic fluorescent nanoparticles, and limitations in popularization and application, and achieves good fluorescence stability and convenience. Large-scale production, bright fluorescent effect

Active Publication Date: 2021-06-22
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] At present, the organic fluorescent molecules used in most organic fluorescent nanoparticles have low fluorescence stability due to the strong intermolecular interaction, which leads to the fluorescence quenching effect, and most of the organic fluorescent nanoparticles use artificially synthesized polymers (such as amphoteric polymers and triblock copolymer) as an encapsulation matrix, resulting in poor biocompatibility of organic fluorescent nanoparticles, which limits its popularization and application.

Method used

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  • Near-infrared two-region fluorescent molecule containing benzobithiadiazole and preparation method thereof, fluorescent nano-particles and preparation method and application thereof
  • Near-infrared two-region fluorescent molecule containing benzobithiadiazole and preparation method thereof, fluorescent nano-particles and preparation method and application thereof
  • Near-infrared two-region fluorescent molecule containing benzobithiadiazole and preparation method thereof, fluorescent nano-particles and preparation method and application thereof

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preparation example Construction

[0048] The invention provides a preparation method of the benzobisthiadiazole-containing near-infrared two-region fluorescent molecule, comprising the following steps:

[0049] (1) Under anhydrous and oxygen-free conditions, 4-bromotriphenylamine and phosphorus oxychloride were subjected to Vilsmeier-Haack reaction in N,N-dimethylformamide, and separated by chromatographic column to obtain formula III respectively compound and the compound shown in formula IV;

[0050]

[0051] (2) Under anhydrous and oxygen-free conditions, carry out a Witting reaction between the compound shown in formula III or the compound shown in formula IV and (triphenylphosphine) ethyl acetate in toluene to obtain the compound shown in formula V or formula VI the indicated compound;

[0052]

[0053] (3) Under anhydrous and oxygen-free conditions, the compound shown in the formula V or the compound shown in the formula VI and the biboronic acid pinacol ester under the action of tetrakis (triphen...

Embodiment 1

[0080] The preparation of the near-infrared two-region fluorescent molecule containing benzobisthiadiazole in formula I:

[0081] (1) Add 11.5g of 4-bromotriphenylamine into a three-necked flask equipped with a magnet. Vacuum three times, under stirring in an ice bath, add dry 80mL N,N-dimethylformamide with a constant pressure separatory funnel, then slowly drop in 30mL phosphorus oxychloride, stir at room temperature for 1 hour, then raise the temperature to Continue the reaction at 95°C for 12 hours. After the reaction, the resulting reaction solution was cooled to room temperature, 330 mL of ice water was added, and then neutralized to neutral with 2 mol / L NaOH solution. Collect the precipitate after suction filtration, dissolve the precipitate with dichloromethane, add anhydrous sodium sulfate to remove water, and finally filter the solution, spin dry with a rotary evaporator, and separate the spin-dried product through a chromatographic column (the eluent is dichloro me...

Embodiment 2

[0086] Preparation of the near-infrared two-region fluorescent molecule containing benzobisthiadiazole in formula II:

[0087] (1) Take 1.34g of the compound of formula IV obtained in Step (1) of Example 1, 2.79g of (triphenylphosphine) ethyl acetate, add it to a 200mL three-necked flask equipped with a magnet, vacuumize three times, and then use a syringe Add 70 mL of deoxygenated toluene, stir and react at room temperature for 48 h, then cool to room temperature, spin dry with a rotary evaporator, and separate through a chromatographic column to obtain the compound represented by formula VI.

[0088] (2) 1.93g of the compound shown in formula VI obtained in step (1), 1.48g of pinacol diborate, 0.28g of tetrakis (triphenylphosphine) palladium and 1.09g of potassium acetate, add a 150mL three-port In the flask, evacuate three times, then add 60mL of deoxygenated dioxane with a syringe, the reaction temperature is 100°C, stir and reflux for 12 hours, spin dry with a rotary evap...

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Abstract

The invention provides a near-infrared two-region fluorescent molecule containing benzobithiadiazole and a preparation method of the near-infrared two-region fluorescent molecule, fluorescent nano-particles and a preparation method and application of the fluorescent nano-particles, and relates to the technical field of fluorescent materials. The near-infrared two-region fluorescent molecule provided by the invention has the characteristics of twisted intramolecular charge transfer and aggregation-induced emission, the quantum yield can be improved, the problem of fluorescence quenching is effectively avoided, and the fluorescence stability is good. The invention also provides the fluorescent nano-particles, which comprise a natural protein nanocage and near-infrared fluorescent molecules encapsulated in the cavity of the natural protein nanocage. The natural protein nanocage is used as a template to encapsulate the near-infrared fluorescent molecules, so that the obtained fluorescent nanoparticles are bright in fluorescence, good in fluorescence stability, high in biocompatibility, uniform in size and can be widely applied to preparation of an angiographic agent or a fluorescent tracer agent.

Description

technical field [0001] The invention relates to the technical field of fluorescent materials, in particular to a near-infrared second-region fluorescent molecule containing benzobisthiadiazole, a preparation method thereof, fluorescent nanoparticles, a preparation method and application thereof. Background technique [0002] NIR imaging has become an important tool for intravital fluorescence imaging and image-guided surgery due to its advantages of high sensitivity, high spatial resolution, high signal-to-book ratio (S / B), noninvasive damage control, deep tissue penetration, and real-time visualization. Especially near-infrared II region (NIR-II) organic fluorescent nanoparticles, which have the excellent characteristics of clinical transformation, low cytotoxicity and easy preparation, have been more and more extensively studied. [0003] At present, the organic fluorescent molecules used in most organic fluorescent nanoparticles have low fluorescence stability due to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C09K11/06C09K11/02B82Y20/00B82Y30/00A61K49/00
CPCC07D513/04C09K11/06C09K11/025B82Y20/00B82Y30/00A61K49/0021A61K49/0093A61K49/0056C09K2211/1081
Inventor 孙跃梁晓翠高千词闵雪红赵兴霖彭凯荣誉陶明洁
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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