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Near infrared fluorescent dye, preparation and application thereof

A fluorescent dye, near-infrared technology, used in azo dyes, organic dyes, luminescent materials, etc., can solve the problems of low detection sensitivity and low detection limit

Inactive Publication Date: 2014-02-19
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Since most of the substances to be tested have no fluorescence or weak fluorescence, and the detection sensitivity is low, people use strong fluorescent labeling reagents or fluorescence generating reagents to label or derivatize the substances to be tested to generate covalent or non-covalent molecules with high fluorescence intensity. The combined substance greatly reduces the detection limit, which is the fluorescent probe

Method used

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  • Near infrared fluorescent dye, preparation and application thereof
  • Near infrared fluorescent dye, preparation and application thereof
  • Near infrared fluorescent dye, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1, the preparation of important precursor

[0028] Compound 1:

[0029] P-bromoacetophenone (9.9g, 50mmol) and potassium hydroxide (8.4mg, 1.5mmol) were added to a round bottom flask, all dissolved in ethanol / water solution (85:15v / v 100mL), and then thiophenecarbaldehyde ( 5.6g, 50mmol), stirred at room temperature for 24h, during this reaction process, the product precipitated from the mixed solution, after the reaction was over, the mixed solution was filtered and recrystallized with ethanol to obtain a yellow solid (13.5g, 92.5%), GC- MS (EI-m / z): theoretical, 291.96; found, 292.

[0030]

[0031] Compound 2:

[0032] Compound 1 (4.9g, 16.8mmol) was weighed and dissolved in 100mL of methanol, nitromethane (5.13g, 84mmol) and diethylamine (6.15g, 84mmol) were added, and heated to reflux for 24h. After the reaction is complete, cool and stand still, acidify to weak acidity with 1mol / L hydrochloric acid, extract and separate the liquids with dichlorome...

Embodiment 2

[0037] Embodiment 2, preparation of aza-BODIPY near-infrared material

[0038] Compound 4a:

[0039]Weigh substance 3 (100mg, 0.15mmol), fluorene monoboronate (164mg, 0.69mmol) and triphenylphosphorous palladium catalyst (7.8mg) into a 25mL two-necked bottle, vacuum blow nitrogen, and inject into the two-necked bottle Toluene (1.5 mL), ethanol (0.75 mL) and 2M potassium carbonate aqueous solution (0.75 mL) were preliminarily sparged with nitrogen for 30 minutes, and heated under reflux overnight. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, and the organic layer was spin-dried and passed through a column (PE:DCM=6:1) to obtain a dark purple solid (94.8 mg, 48.6%). 1 H NMR (400MHz, CDCl 3 )δ: 8.20 (d, J = 8.2Hz, 4H), 7.97 (d, J = 3.2Hz, 2H), 7.85-7.71 (m, 8H), 7.69-7.62 (m, 4H), 7.59 (d, J =4.8Hz, 2H), 7.40-7.30(m, 6H), 7.25-7.19(m, 2H), 7.03(s, 2H), 2.12-1.93(m, 8H), 1.33-0.99(m, 40H), 0.81 (t, J = 6.9 Hz, 12H) 0.74-0...

Embodiment 3

[0044] Embodiment 3, substituting group is the aza BODIPY of fluorene to Hg in solution 2+ Titration experiment

[0045] Prepare a 10 μM solution of azaBODIPY (4a) whose substituent is fluorene (HPLC dichloromethane as a solvent), pipette 2.5 mL of the compound solution into a fluorescent cuvette, and gradually add 1.25×10 -3 mol / LHg 2+ solution (acetonitrile as solvent), measure its ultraviolet-visible absorption spectrum and fluorescence spectrum respectively until the spectrum reaches equilibrium (that is, the spectrum no longer changes significantly). Test data show that with Hg 2+ With the addition of , the color of the compound solution changed significantly, from light purple to light blue, and the fluorescence was gradually quenched.

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Abstract

The invention belongs to the technical field of organic photoelectric functional material, and specifically provides a preparation method of an aza BODIPY based near infrared fluorescent dye and application of the near infrared fluorescent dye to Hg<2+> detection, cell imaging and biomarker. The material is a micromolecular near infrared dye based on aza BODIPY, and near infrared absorption and emission wavelength of which are adjusted by changing Ar group. The material has a structural general formula shown as below, simple synthesis steps with mild conditions, can be used as a near infrared fluorescent material and has good application prospect in ion detection, cell imaging and biomarker.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials. It specifically relates to a preparation method of a kind of near-infrared absorbing and emitting fluorescent material and its application in ion detection, cell imaging and biomarker. Background technique [0002] Since most of the substances to be tested have no fluorescence or weak fluorescence, and the detection sensitivity is low, people use strong fluorescent labeling reagents or fluorescence generating reagents to label or derivatize the substances to be tested to generate covalent or non-covalent molecules with high fluorescence intensity. The combined substance greatly reduces the detection limit, which is the fluorescent probe. [0003] Because many organisms and their tissues emit fluorescence under the excitation of visible light, coupled with the influence of light scattering, it often produces more serious background interference, which seriously ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C09K11/06G01N21/64C12Q1/02
Inventor 黄维赵强刘淑娟袭娜
Owner NANJING UNIV OF POSTS & TELECOMM
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