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Polarity-sensitive triphenyl pyridinium fluorescent probe as well as preparation and application thereof

A technology of triphenylpyridinium salt and fluorescent probe, which is applied in the field of fluorescent sensors, can solve the problems of weakening fluorescence intensity and changing luminescence wavelength, and achieve the effects of weakening fluorescence intensity and reducing quantum yield

Inactive Publication Date: 2020-11-20
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a polarity-sensitive triphenylpyridinium salt fluorescent probe and its preparation and application, aiming at solving the problem that the existing polarity-sensitive fluorescent probes do not have solvent Problems with atypical AIE properties of increased polarity, altered emission wavelength and reduced fluorescence intensity

Method used

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  • Polarity-sensitive triphenyl pyridinium fluorescent probe as well as preparation and application thereof
  • Polarity-sensitive triphenyl pyridinium fluorescent probe as well as preparation and application thereof
  • Polarity-sensitive triphenyl pyridinium fluorescent probe as well as preparation and application thereof

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preparation example Construction

[0031] The embodiment of the present invention provides a method for preparing a polarity-sensitive triphenylpyridinium salt fluorescent probe as described above, according to the reaction formula Include steps:

[0032] A. Under an inert atmosphere, (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one, containing R 1 Acetophenone and excess boron trifluoride ether carry out the first reaction in the first solvent to obtain the pyryl salt intermediate;

[0033] The containing R 1 Acetophenone is R 1 Is H, halogen atom or methoxy group; pyryl salt intermediate is

[0034] B. Under an inert atmosphere, pyryl salt intermediates and R-containing 2 The amine compound is subjected to a second reaction in a second solvent to obtain a fluorescent probe;

[0035] The containing R 2 The amine compound is R 2 -NH 2 , R 2 is an alkyl or substituted alkyl.

[0036] In this example, the preparation method of the triphenylpyridinium salt fluorescent probe is simple, easy to operate...

Embodiment 1

[0045] The preparation of embodiment 1 (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one

[0046] According to the reaction formula Prepare as follows:

[0047] Benzaldehyde (1eq, 3.00g, 28.27mmol) and 4-methoxyacetophenone (1eq, 4.25g, 28.27mmol) were dissolved in 200mL of ethanol (EtOH), and 1.13g of NaOH was dissolved in 10mL of water while stirring to form The alkaline solution of the above mixture was added dropwise, then 50 mL of water was added, and the reaction was stirred at room temperature for 5 h, resulting in precipitation. After the reaction, the reaction solution was filtered, the precipitate was collected, and washed with water and cold ethanol to obtain 5.74g (E)-1-(4-methoxyphenyl)-3-phenylprop-2-ene-1 - Ketone, a white solid, yield 85.21%. Its structural identification data are: 1 H NMR (500MHz, CDCl 3 )δ8.04(d,J=8.9Hz,2H),7.80(d,J=15.7Hz,1H),7.65–7.63(m,2H),7.55(d,J=15.7Hz,1H),7.43– 7.38(m,3H),6.98(d,J=8.9,2H),3.88(s,3H). 13 C NMR (125MHz, CDCl 3 )δ1...

Embodiment 2

[0048] Embodiment 2 fluorescent probe (R 1 =Br, R 2 =n-C 5 h 11 ) is prepared according to the reaction formula Prepare as follows:

[0049] (1) Under an argon atmosphere, (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (1.00eq, 100mg, 0.42mmol), 4 -Bromoacetophenone (3.0eq, 251mg, 1.259mmol), BF 3 ·Et 2 O (10mL) and dichloromethane (DCM) were mixed, and the reaction mixture was vigorously stirred overnight (about 12h) at 45°C. After the reaction was completed, it was cooled to room temperature; 50mL of diethyl ether (Et 2 O), vigorously stirred to make the pyryl salt intermediate (R 1 =Br) precipitated from the reaction solution, filtered, and washed with Et 2 O washes precipitate, obtains 112mg pyryl salt intermediate (R 1 =Br), the yield was 52.8%.

[0050] (2) Under an argon atmosphere, the pyryl salt intermediate (R 1 =Br) (1.0eq, 500mg, 1.03mmol), 1-amylamine ((1.2eq, 125.03mg, 1.43mmol) and ethanol (15mL) were mixed, and the reaction mixture was heated to 80...

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Abstract

The invention discloses a polarity-sensitive triphenyl pyridinium salt fluorescent probe and preparation and application thereof. The structural general formula of the fluorescent probe is shown in the specification, and R1 is H, a halogen atom or a methoxy group; and R2 is alkyl or substituted alkyl. The pyridinium salt part in the fluorescent probe with the structure is used as an electron acceptor (Acceptor, A) and has very strong electron withdrawing capability, and meanwhile, the three benzene ring parts in the fluorescent probe are used as an electron donor (Donor, D) and can provide proper electron donating capability; the fluorescent probe with a D-A structure formed in this way has certain fluorescence capability and atypical AIE properties; the solid fluorescence quantum yield is20% or above; in a certain polarity range, along with the enhancement of the solvent polarity, the luminescence red shift in the solvent is realized, the fluorescence intensity is weakened, and the quantum yield is reduced.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensors, in particular to a polarity-sensitive triphenylpyridinium salt fluorescent probe and its preparation and application. Background technique [0002] Fluorescence spectroscopy is a very important tool in the identification of ions, detection of small molecules, and biochemical studies of biological processes such as protein folding, protein-protein interactions, and phosphorylation. [0003] Polarity can be seen everywhere in people's living environment, such as the natural environment in which people live, the environment in vivo, cells, and organelles, etc., are all subtly related to the polarity of their environment, and the polarity of solvents is used in experiments and research. It is also extremely important. Fluorescent probes sensitive to polar environments are a special class of fluorescent probes whose spectral properties change with changes in the surrounding polar environm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30C09K11/06G01N21/64
CPCC07D213/30C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 刘一冯阳林发旭
Owner SHENZHEN UNIV
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