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High-sensitivity fluorescent compound PPAB detecting organic primary amine with naked eyes and application of fluorescent chemical PPAB

A technology of fluorescent compounds and organic primary amines, which is applied in the field of analysis and detection, can solve the problems of low sensitivity and achieve the effects of improved sensitivity, rapid response and easy operation

Active Publication Date: 2019-07-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the fluorescent probes of organic amines are all compounds with a single reaction site, so the sensitivity is low

Method used

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  • High-sensitivity fluorescent compound PPAB detecting organic primary amine with naked eyes and application of fluorescent chemical PPAB
  • High-sensitivity fluorescent compound PPAB detecting organic primary amine with naked eyes and application of fluorescent chemical PPAB
  • High-sensitivity fluorescent compound PPAB detecting organic primary amine with naked eyes and application of fluorescent chemical PPAB

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The reaction equation for preparing the fluorescent compound PPAB1 is:

[0035]

[0036] (1) Compound 1 was prepared according to the method disclosed in G.M.Fischer, M.Isomaeki-Krondahl, I.Goettker-Schnetmann, E.Daltrozzo and A.Zumbusch, Chemistry-A European Journal, 2009, 15, 4857-4864.

[0037] (2) Dissolve compound 1 (365mg, 0.67mmol) and compound 2 (1110mg, 5.36mmol) in 40mL toluene, heat the reaction system to 50°C, stir for 10 minutes, then add triethylamine (2.24g, 22.11mmol) and TiCl 4 (1.52g, 8.04mmol), TLC detects that after the raw material has reacted, add BF to the reaction solution 3 -Et 2 O (2.63g, 18.56mmol), continue to stir for 30 minutes, pour the reaction solution into 200mL water, and use CH 2 Cl 2 Extracted 3 times, anhydrous NaSO 4 Drying, filtration, rotary evaporation to remove the solvent, separation by silica gel column chromatography to obtain the crude product of PPAB1, which was washed with CH 2 Cl 2 Recrystallization from methan...

Embodiment 2

[0040] PPAB1 was dissolved in 1,4-dioxane to obtain the probe mother solution (10 -3 mol / L), followed by adding 1,4-dioxane to dilute to obtain 10 -5 mol / L PPAB1 solution, add 1,3-propanediamine solution (4×10 -5 mol / L), to test the change of its ultraviolet spectrogram in different reaction time, from figure 2 It can be seen that the intensity of the absorption peaks at 680nm and 630nm decreased rapidly, the absorption peak at 450nm shifted red to 480nm, and reached equilibrium in 3 minutes, and the color of the solution changed from green to yellow.

Embodiment 3

[0042] PPAB1 was dissolved in 1,4-dioxane to obtain the probe mother solution (10 -3 mol / L), followed by adding 1,4-dioxane to dilute to obtain 10 -5 mol / L PPAB1 solution, add 1,3-propanediamine solution (4×10 -5 mol / L), to test the change of its fluorescence spectrum in different reaction time, from image 3 It can be seen that the fluorescence intensity at 695nm decreased, the fluorescence at 518nm shifted to 544nm and reached equilibrium in 3 minutes with the increase of fluorescence intensity.

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Abstract

The invention discloses a high-sensitivity fluorescent compound PPAB detecting organic primary amine with naked eyes and application of the fluorescent chemical PPAB. The PPAB is obtained in a mannerthat diketopyrrolopyrrole and nitrogen-containing aromatic primary amine are subjected to a condensation reaction, and the diketopyrrolopyrrole and BF3.Et2O are subjected to coordination interaction in situ. Boron atoms and nitrogen atoms in organic amine can react, imine linkages are easy to react in the presence of the organic amine, the multiple imine linkages and the multiple boron atoms are simultaneously introduced into the compound, multiple reaction sites are introduced, the fluorescent compound PPAB is used for detecting aliphatic primary amine, and in the detecting process, the high-sensitivity fluorescent compound PPAB has the advantages that operation is easy and convenient, reacting is rapid, the selectivity is good, the anti-photobleaching performance of fluorescence signalsis excellent, and color comparison and fluorescence dual-mode detecting is achieved, and the high-sensitivity fluorescent compound PPAB can be used for environment monitoring, food safety detection and the like.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, and in particular relates to a fluorescent compound PPAB capable of detecting primary organic amines with high sensitivity and an application thereof. Background technique [0002] As an important chemical raw material and intermediate, organic amines are widely used in industry, agriculture, medicine and other fields, and can be used as pharmaceutical intermediates, accelerators, metal preservatives, emulsifiers, etc. Among them, most of the amines are strongly irritating and corrosive, and can irritate the eyes, trachea, lungs, skin and excretory system. Inhalation of high concentrations can be fatal. Therefore, the detection of organic amines is important in chemical substance leakage, food safety and environmental testing. field is of great importance. At present, the detection methods of organic amines include electrochemical method, chromatographic analysis method, and color...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64G01N21/33
CPCC07F5/022C09K11/06G01N21/6428G01N21/33C09K2211/1037
Inventor 汪凌云李兰清曹德榕
Owner SOUTH CHINA UNIV OF TECH
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