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Fluorescent probe for detecting hydrazine or amine substance gas and preparation method thereof

A technology of amine substances and fluorescent probes, which is applied in the field of organic fluorescent sensor materials, can solve the problems of difficult synthesis, inconvenient manufacture of portable, complex compound structures, etc.

Inactive Publication Date: 2017-07-07
北京知元科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these compounds have the possibility of detecting amine gas, their synthesis and utilization make it possible to develop easy-to-use fluorescent sensors for amine gas detection, but there are still compounds with complex structures and difficult synthesis, which are not easy to make into portable sensors. , solid-state fluorescence detector suitable for on-site detection of amine gas, etc.

Method used

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  • Fluorescent probe for detecting hydrazine or amine substance gas and preparation method thereof
  • Fluorescent probe for detecting hydrazine or amine substance gas and preparation method thereof
  • Fluorescent probe for detecting hydrazine or amine substance gas and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] According to the synthetic route of the present invention, synthesize the compound of formula II with the following specific structure:

[0107] (1) Synthesis of Compound II-1: 2-[2-hydroxyphenyl]-4-(3H)-quinazolone (R 1 = H, R 2 =H)

[0108]

[0109] Anthranilamide (272mg, 2mmol), salicylaldehyde (244mg, 2mmol) and iodine (508mg, 2mmol) were placed in 15mL of ethanol and reacted under reflux for 6 hours. After the reaction was completed, 5% by mass fraction of sodium thiosulfate solution was added to remove unreacted iodine. A large amount of white precipitate precipitated out of the reaction solution, which was filtered, washed with water (10 mL×2) and ethanol (10 mL×2), and dried in vacuo to obtain a white solid with a mass of 390 mg (yield 82%).

[0110] 1 H NMR (d 6 -DMSO,500MHz):13.78(br s,1H),12.48(br s,1H),8.23(dd,J 1 =8.0Hz,J 2 =1.5Hz,1H),8.16(dd,J 1 =8.0Hz,J 2 =1.5Hz,1H),7.86(td,J 1 =8.5Hz,J 2 =1.5Hz, 1H), 7.77(d, J=8.0Hz, 2H), 7.56(td, J 1 =8.0...

Embodiment 2

[0128] According to the synthetic route of the present invention, the formula I compound of following specific structure is synthesized on the basis of the compound of Example 1:

[0129] (1) Synthetic (R 1 = H, R 2 = H, R 3 = methyl)

[0130]

[0131] 2-[2-Hydroxyphenyl]-4-(3H)-quinazolinone (280mg, 1.0mmol) was added to 5mL methanol solution dissolved with sodium methoxide (108mg, 2.0mmol), and reacted at room temperature under nitrogen protection 5 minutes. After the reaction solution became clear, methanol was removed by rotary evaporation. Subsequently, 10 mL of THF and acetic anhydride (408 mg, 4.0 mmol) were added and reacted at room temperature for 2 hours under nitrogen protection. After the reaction was completed, THF was removed by rotary evaporation, the residue was washed with water, and then dried in vacuo to obtain a white solid with a mass of 266 mg (yield: 95%).

[0132] 1 H NMR (CDCl 3 ,500MHz):10.42(br s,1H),8.29(dd,J 1 =7.5Hz,J 2 =1.0Hz,1H),8.0...

Embodiment 3

[0140] Fluorescence property test of formula I compound and formula II compound

[0141] 1. Fluorescence quantum yield is measured by C11347 Quantaurus_QY instrument.

[0142] 2. Research method of fluorescence emission spectrum in tetrahydrofuran / water:

[0143] tetrahydrofuran and water according to different volume ratios (THF: water = 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, 1:99) to form mixed solutions with different water contents, compound I-1 and compounds II-1~II-5 were dissolved in these mixed solutions respectively, so that the concentration of the compound was 10 -5 mol L -1 , Record the fluorescence emission of compound I-1 and compounds II-1~II-5 in these solvent systems with appropriate excitation light.

[0144] see attached results Figure 1-6 . When the water content in the mixed solution system is continuously increased, the solubility of compounds II-1-II-5 gradually decreases and thus aggregates, and the fluorescence inte...

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Abstract

The invention relates to a quinazolinone compound. The compound does not laminate in a solid state, and in the effects of hydrazine or amine substance gas, aminolysis or hydrolysis reaction of ester function group-O-C(O)-R3 is carried out, hydroxy is released, interaction between O-H of hydroxy and N of C=N in a quinazolinone ring is carried out, and an intramolecular six-membered ring hydrogen bond is formed; because of intramolecular rotation limit and excitation state intramolecular proton transfer mechanism, strong fluorescence is emit in a solid state. The compound can be used as a fluorescent probe for detecting hydrazine or amine substance gas.

Description

technical field [0001] The invention relates to a quinazolinone compound with aggregation-induced luminescent properties, and its preparation method and application, especially its application in gas detection of hydrazine or amine substances, belong to the field of organic fluorescent sensor materials. Background technique [0002] Amines are widely used in chemical industry, medicine, agriculture and other fields. According to the number of hydrogens replaced, amines can be divided into primary amines (primary amines) RNH 2 , secondary amine (secondary amine) R 2 NH, tertiary amine (tertiary amine) R 3 N, quaternary ammonium salt (quaternary ammonium salt) R 4 N + x – . According to the different types of groups connected to the nitrogen atom in the amine molecule, it can be divided into aliphatic amines and aromatic amines. If the amine molecule contains two or more amino groups (-NH 2 ), according to the number of amino groups, it can be divided into diamines and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D239/91G01N21/64
CPCC07D239/91C09K11/06C09K2211/1007C09K2211/1044G01N21/643
Inventor 唐本忠高蒙秦安军
Owner 北京知元科技有限公司
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