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Aggregation-induced emission probe based on quinazolinones compound as well as preparation method and application of aggregation-induced emission probe

A technology for quinazolinone and compound, which is applied in the application field of quinazolinone compound and ammonia gas detection, and can solve the problems of difficult synthesis, complex compound structure, inconvenience of making it portable, etc.

Active Publication Date: 2017-05-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis and utilization of these compounds have gradually made it possible to develop an easy-to-use fluorescent sensor for ammonia detection, there are still complex structures and difficulties in synthesis, which make it difficult to make a portable solid-state fluorescence sensor suitable for on-site detection of ammonia. deficiencies

Method used

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  • Aggregation-induced emission probe based on quinazolinones compound as well as preparation method and application of aggregation-induced emission probe
  • Aggregation-induced emission probe based on quinazolinones compound as well as preparation method and application of aggregation-induced emission probe
  • Aggregation-induced emission probe based on quinazolinones compound as well as preparation method and application of aggregation-induced emission probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] According to the synthetic route of the present invention, synthesize the compound of formula II with the following specific structure:

[0117] (1) Synthesis of Compound II-1: 2-[2-hydroxyphenyl]-4-(3H)-quinazolone (R 1 = H, R 2 =H)

[0118]

[0119] 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%).

[0120] 1 H NMR (d 6 -DMSO,500MHz):δ13.78(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....

Embodiment 2

[0138] 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:

[0139] (1) Synthetic (R 1 = H, R 2 = H, R 3 = methyl)

[0140]

[0141] 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%).

[0142] 1 H NMR (CDCl 3 ,500MHz):δ10.42(br s,1H),8.29(dd,J 1 =7.5Hz,J 2 =1.0Hz,1H),8....

Embodiment 3

[0150] Fluorescence property test of formula I compound and formula II compound

[0151] 1. Fluorescence quantum yield is measured by C11347 Quantaurus_QY instrument.

[0152] 2. Research method of fluorescence emission spectrum in tetrahydrofuran / water:

[0153] 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 , using appropriate excitation light to detect the fluorescence emission of compound I-1 and compounds II-1-II-5 in these solvent systems.

[0154] 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 ...

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Abstract

The invention relates to a quinazolinones compound. The compound does not emit light under a solid state; however, an ester functional group -O-C(O)-R3 is subjected to ammonolysis reaction under the action of ammonia gas to realize hydroxyl; O-H of the hydroxyl and N of C=N in a quinazolinone ring have a mutual effect to form an intramolecular six-membered ring hydrogen bond; strong fluorescent light is emitted under the solid state due to an intramolecular rotation restricted and excited-state intramolecular proton transferring mechanism. The compound can be used as a fluorescent probe and is used for detecting the ammonia gas; furthermore, the compound can be used as a detection reagent for detecting the corrosion degree of foods and an invisible ink material with an AND logic gate.

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 ammonia gas detection, belong to the field of organic fluorescent sensor materials. Background technique [0002] Ammonia and its derivatives are widely used in chemical industry, medicine, agriculture, refrigeration and other fields, and are important raw materials for the manufacture of fertilizers, explosives, and medicines. At the same time, ammonia gas is highly corrosive and irritating, and is a common air pollutant, which mainly comes from chemical plant leakage, fuel combustion, and decomposition of nitrogen-containing organic matter. Taking the decay and decomposition of nitrogen-containing organic matter as an example, data show that in high-density livestock and poultry breeding areas, the excessive release of ammonia in agricultural production has led to direct or indire...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C09K11/06G01N21/64C09D11/50C09D11/16
CPCC07D239/91C09D11/16C09D11/50C09K11/06C09K2211/1007C09K2211/1044G01N21/6428
Inventor 唐本忠高蒙李诗武秦安军
Owner SOUTH CHINA UNIV OF TECH
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