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Preparation method and time-resolved biological imaging application of thermally activated delayed long-life fluorescent organic material-based nanoparticles

A technology of thermally induced delayed fluorescence and fluorescent nanoparticles, which is applied in the fields of luminescent materials, material excitation analysis, organic chemistry, etc., can solve the problems that the signal is easily affected by the environment, the sensitivity and signal-to-noise ratio are low, and the hydrophobicity is easy to aggregate. Good fluorescence lifetime stability, long fluorescence lifetime, uniform size effect

Active Publication Date: 2016-03-16
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing organic dyes still face some problems such as hydrophobicity, easy aggregation, easy photobleaching, etc.
However, although inorganic semiconductor nanocrystals, such as quantum dots, have the advantages of high brightness and high photostability, their own toxicity needs to be solved urgently.
In addition, the application of general fluorescent dyes in biological imaging is susceptible to the interference of endogenous background fluorescence in biological systems, the sensitivity and signal-to-noise ratio are relatively low, and the signal is easily affected by the environment.

Method used

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  • Preparation method and time-resolved biological imaging application of thermally activated delayed long-life fluorescent organic material-based nanoparticles
  • Preparation method and time-resolved biological imaging application of thermally activated delayed long-life fluorescent organic material-based nanoparticles
  • Preparation method and time-resolved biological imaging application of thermally activated delayed long-life fluorescent organic material-based nanoparticles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In a two-neck flask (100mL), dissolve 2-bromonitrobenzene (2.01g, 10mmol) and 2-thiopheneboronic acid (1.42g, 11mmol) in 30mL of toluene, inject 20mL of 2M potassium carbonate solution, and pump three times. Under nitrogen protection, tetrakis(triphenylphosphine)palladium (150mg, 0.14mmol) was added, heated to 90°C, and reacted for 16 hours. Naturally cooled to room temperature, extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain 1.85 g of bright yellow powder with a yield of 81%. 1 HNMR (400MHz, CDCl3 )δ7.95(d, J=1.9Hz, 1H), 7.77(dd, J=8.1, 1.9Hz, 1H), 7.56(d, J=8.1Hz, 1H), 7.42(d, J=1.0Hz, 1H), 7.39(dd, J=5.1, 1.1Hz, 1H), 7.11(d, J=1.4Hz, 1H). 13 CNMR (101MHz, CDCl 3 ) δ 141.03, 132.68, 128.69, 128.53, 127.94, 127.50, 127.24, 127.21, 126.71, 124.88, 120.74.

[0035]

[0036] Add 2-nitro-phenylthiophene (9.37g, 33mmol), triphenylphosphine (22.7g, 100mmol) and chlorobenzene (60mL) into a two-necked round bottom fla...

Embodiment 2

[0043] Add the above-mentioned benzothienopyrrole (6.05g, 48mmol), 2,3,5,6-tetrafluoro-4-cyanopyridine (1.76g, 10mmol), potassium carbonate (9.6g, 70mmol) and dimethyl sulfoxide (100mL), under nitrogen protection, stirred at 150°C for 24h. Extract with dichloromethane and dry over anhydrous sodium sulfate. Concentrate and separate on a silica gel column to obtain CzPy, 6.34g, with a yield of 82%. 1 HNMR (400MHz, CDCl 3 )δ7.59(d, J=8.4Hz, 1H), 7.50(d, J=1.6Hz, 1H), 7.39(d, J=5.2Hz, 1H), 7.27-7.24(dd, J=1.7Hz, 1H), 7.02(d, J=5.2Hz, 1H), 4.06(d, J=7.5Hz, 2H), 2.04(m, 1H), 1.28(m, 24H), 0.84-0.89(m, 6H). 13 CNMR (101MHz, CDCl 3 )δ146.16,142.42,127.29,122.03,121.30,119.97,115.84,115.73,113.02,110.56,49.79,38.37,31.88,31.78,31.68,31.6,29.90,29.58,29.50,29.27,26.4,26.40,22.68,22.63,14.14 , 14.10.

[0044]

[0045]

[0046]

[0047] Example 3

Embodiment 3

[0049] In a two-neck flask (100 mL), 2-bromonitrobenzene (2.01 g, 10 mmol), 2-naphthylboronic acid (1.86 g, 11 mmol) were dissolved in 30 mL of tetrahydrofuran, and 20 mL of 2M potassium carbonate solution was injected. The gas was exchanged three times. Under the protection of nitrogen, tetrakis(triphenylphosphine)palladium (150mg, 0.14mmol) was added, heated to 90°C, and reacted for 16 hours. Naturally cooled to room temperature, extracted with dichloromethane, dried, concentrated, and separated by column chromatography to obtain 1.67 g of bright yellow powder with a yield of 65%. 1 HNMR (400MHz, CDCl 3 )δ8.05(d,J=1.9Hz,1H),8.00(m,3H),7.90(t,2H),7.75(m,1H),7.64(s,1H),7.56(d,J=8.1 Hz, 2H). 13 CNMR (101MHz, CDCl 3 ) δ 141.13, 136.68, 134.21, 133.1, 132.7, 130.45, 128.5, 128.2, 128.1, 127.7, 126.69, 124.4.

[0050]

[0051] Add 2-nitro-phenylbinaphthyl (2.5g, 10mmol), triphenylphosphine (6.3g, 28mmol) and chlorobenzene (22mL) into a two-necked round bottom flask (250mL),...

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Abstract

The invention discloses a preparation method and a time-resolved biological imaging application of thermally activated delayed fluorescent (TADF) organic material-based water-soluble long-life fluorescent nanoparticles. The nanostructure of the nanoparticles is represented by figure 1, a thermally activated delayed fluorescent molecule represented by CzPy is represented by a general formula (I). The method comprises the following steps: synthesizing the pure organic TADF micro-molecular material CzPy through adopting a one-step process, and rapidly injecting a CzPy / lecithin-polyethylene glycol mixed solution to deionized water to obtain the CzPy nanoparticles with good water solubility, high luminescence intensity and long fluorescence life. HELA cell dyeing marking and zebra blood vessel imaging results show that the nanoparticles have the advantages of long fluorescence life, low cytotoxicity and biotoxicity, stable spectrum signal, realization of time-resolved fluorescence imaging in cell or in vivo imaging, and good application prospect.

Description

technical field [0001] The invention relates to a preparation method and biological imaging application of synthesizing long-lived organic fluorescent molecules with thermally induced delayed fluorescence (TADF) characteristics and water-soluble long-lived nanoparticles. The invention belongs to the field of organic light-emitting materials, nano-biological probes and imaging. Background technique [0002] As a non-invasive biosensing technology, fluorescence microscopy has become an essential key technology in cell imaging, in vivo, and in vitro tissue imaging. The core of fluorescence microscopy imaging technology is to develop fluorescent chromophores with high fluorescence efficiency and good photostability. Currently common fluorescent chromophores include: traditional fluorescein, rhodamine, cyanine organic dyes, inorganic semiconductor nanocrystals, conjugated polymers, etc. Among them, traditional organic small molecule fluorescent dyes have become the main choic...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09K11/02C07D519/00C07D401/14G01N21/64A61K49/00
Inventor 汪联辉傅妮娜李亭亭翟柳青杨栋梁王遂良赵保敏
Owner NANJING UNIV OF POSTS & TELECOMM
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