Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof

A technology of triphenylamine pyridinium salt and fluorescent molecules, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, and can solve problems such as difficult separation, high price, and low synthesis yield

Inactive Publication Date: 2014-07-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Near-infrared organic functional dyes as fluorescent probe molecules are expensive, low synthesis yield, and difficult to separate

Method used

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  • Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof
  • Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof
  • Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1. The preparation method of triphenylamine-pyridinium salt TPA-PyS

[0019] (1) Under nitrogen protection and anhydrous and oxygen-free conditions, triphenylamine iodide 4-[N,N-bis(4-iodophenyl)amino]benzaldehyde (TPA-I) (prepared according to the literature method, reference: Tetrahedron Letters, 2007, 48, 5878) and 4-vinylpyridine through palladium-catalyzed coupling reaction to prepare triphenylamine-pyridine compound 4-[N,N-bis(4-pyridylvinylphenyl)amino]benzaldehyde (TPA -Py), the synthetic route is as follows:

[0020]

[0021] The specific preparation method is: under nitrogen protection and anhydrous and oxygen-free conditions, dissolve 0.53g (1.0mmol) of 4-[N,N-bis(4-iodophenyl)amino]benzaldehyde in 10mL of anhydrous N,N- To dimethylacetamide were added 0.023 g (0.1 mmol) of palladium acetate, 0.061 g (0.2 mmol) of tris(o-methylphenyl)phosphine, and 0.60 g (2.8 mmol) of anhydrous potassium phosphate. Under magnetic stirring, 1.5 mL of 4-vinylpy...

Embodiment 2

[0033] Example 2. Red emission of triphenylamine-pyridinium salt TPA-PyS

[0034] The solid state of triphenylamine-pyridinium salt (TPA-PyS) emits red fluorescence, and the fluorescence emission peak is 656nm, which is located in the near-infrared region. attached figure 1 Fluorescence spectrum of the triphenylamine pyridinium salt TPA-PyS solid powder prepared in Example 1 of the present invention. The solid state emits red fluorescence under ultraviolet light in a dark room.

[0035] The pyridinium salt compound of the present invention is soluble in water, emits red light in water, the wavelength is 647nm, and figure 2 The ultraviolet-visible absorption spectrum and fluorescence spectrum of the triphenylamine pyridinium salt TPA-PyS prepared in Example 1 of the present invention in aqueous solution.

Embodiment 3

[0036] Example 3. Fluorescent probe properties of triphenylamine-pyridinium salt TPA-PyS

[0037] Under the physiological environment of pH 7.4, Na 2 HPO 4 -NaH 2 PO 4 As a buffer system, keep the probe molecule TPA-PyS concentration at 10 -6 M, BSA concentration gradually increased from 0 to 4.0×10 -6 M, the fluorescence spectrum of the measurement system. attached image 3 Fluorescence spectrum of the interaction between triphenylamine pyridinium salt TPA-PyS prepared in Example 1 of the present invention and bovine serum albumin. The near-infrared fluorescence intensity of TPA-PyS increased rapidly with the increase of bovine serum albumin BSA concentration, and the position of the fluorescence peak shifted significantly. Triphenylamine pyridinium salt TPA-PyS is soluble in water, has near-infrared emission fluorescence characteristics, and can be used as a near-infrared fluorescent probe for the detection of bovine serum albumin BSA.

[0038]The triphenylamine pyri...

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Abstract

The invention discloses a triphenylamine pyridinium salt fluorescent molecule and a preparation method thereof. The red light emitting triphenylamine pyridinium salt fluorescent molecule is obtained by carrying out a reaction on 4-[N, N-bi(4-pyridine vinyl) phenyl amino] benzaldehyde and iodooctadecane in an acetone solution. The pyridinium salt compound disclosed by the invention emits red light when the compound is solid, wherein the wavelength is 656nm. The pyridinium salt compound disclosed by the invention is water-soluble and emits red light in water, wherein the wavelength is 647nm. In a water / ethanol mixed solvent, the emitting wavelength is in a band of 610-640nm. The pyridinium salt compound disclosed by the invention has a red light emitting property and has an important application value in the fields such as fluorescence sensors, fluorescence probes, biomarkers, fluorescence imaging and organic light-emitting apparatuses.

Description

technical field [0001] The invention relates to a pyridinium salt organic fluorescent compound, and specifically designs a triphenylamine pyridinium salt compound and its preparation. Background technique [0002] Proteins, amino acids, and DNA are the most important basic components of organisms, and are closely related to various life activities such as immunity and metabolism. Using the fluorescent properties of fluorescent probe molecules to study the interaction between fluorescent probe molecules and proteins, amino acids, and DNA can provide extremely useful information for the study of life activities. Fluorescent probe technology has the characteristics of fast, sensitive, and high-throughput, and has been widely used in the fields of nucleic acid, protein, and cell detection and immunoassay. Near-infrared organic functional dyes as fluorescent probe molecules are expensive, have low synthesis yields, and are difficult to separate. Designing and developing red-lig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C09K11/06G01N33/68G01N21/64
CPCC07D213/36C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029G01N21/6486
Inventor 钱鹰陶在琴
Owner SOUTHEAST UNIV
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