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Dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe as well as preparation method and application thereof

A technology for fluorescent probes and methyl dehydroabietate, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high sample standard requirements and high professional operation

Pending Publication Date: 2022-05-27
NANJING FORESTRY UNIV
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  • Abstract
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Problems solved by technology

[0004] Although there are many methods for detecting metal ions, such as atomic absorption method, spectrophotometry, cyclic voltammetry, etc., these methods have a series of problems and limitations, such as strict detection environment, high sample standard requirements, high professionalism in operation, etc. , the fluorescent probe method has the advantages of fast detection speed, wide detection environment and high sensitivity
[0005] In recent years, people have studied a lot of fluorescent probes for metal detection technology, such as coumarin-based fluorescent probes to detect mercury ions, rhodamine-based fluorescent probes to detect ferric ions, but no dehydroabietic acid Schiff base was synthesized. Related reports on the detection of mercury ions, copper ions and hypochlorite ions by quasi-fluorescent probes

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  • Dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe as well as preparation method and application thereof
  • Dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe as well as preparation method and application thereof
  • Dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0049] The present embodiment provides a method for preparing a dehydroabietate-based Schiff base multi-ion functional fluorescent probe, and the specific steps are as follows:

[0050] (1) preparation of 12-bromo-13-nitrodehydroabietic acid methyl ester: dehydroabietic acid is obtained through methyl esterification, bromination and nitration reaction, see figure 1 , the specific process is as follows:

[0051] Weigh 30 g of dehydroabietic acid and dissolve it in 60 mL of toluene, add 11 mL of thionyl chloride, react at 78-80 °C for 3 h, spin dry in vacuo, add 60 mL of methanol, react at 78-80 ° C for 3 h, spin dry, Add 30 mL of ethanol to dissolve the crystal to obtain methyl dehydroabietate;

[0052] Accurately weigh 5 g of methyl dehydroabietate, dissolve it in 30 mL of acetonitrile, add 4 g of N-bromosuccinimide, react at room temperature in the dark for 24 h, spin to evaporate, wash twice with dichloromethane, and dissolve the crystals in 100 mL of methanol to obtain Me...

Embodiment 2

[0062] Optimization of the Preparation Method of Dehydroabietate Schiff Base Derivatives:

[0063] Test 1: Accurately weigh 0.1 g of methyl 12-bromo-13-aminodeisopropyl dehydroabietate and 0.052 g of 3-(1H-benzo[d]imidazol-2-yl)-2-hydroxy-5 -methylbenzaldehyde, sonicated in 10 ml of absolute ethanol, the temperature was 78 ° C, refluxed and stirred for 12 hours, after the reaction was completed, placed at room temperature for recrystallization to obtain pure probe CPY with a yield of 72%.

[0064] Test 2: Accurately weigh 0.1 g of methyl 12-bromo-13-aminodeisopropyl dehydroabietate and 0.052 g of 3-(1H-benzo[d]imidazol-2-yl)-2-hydroxy-5 -methylbenzaldehyde, sonicated in 10ml of absolute ethanol, the temperature was 90°C, refluxed and stirred for 12 hours, after the reaction was completed, placed at room temperature for recrystallization to obtain pure probe CPY with a yield of 62%.

[0065] Test 3: Accurately weigh 0.1 g of methyl 12-bromo-13-aminodeisopropyl dehydroabietate ...

Embodiment 3

[0074] Dissolve the probe CPY in absolute ethanol to prepare 1 × 10 -3 M solution, take 200 μL of the stock solution and add it to 10 ml of ethanol aqueous solution (ethanol:water 7:3) to prepare 2×10 -5 M solution, add 5 μL Cu each time 2+ (1×10 -3 M), 50 μL ClO - (1×10 -3 M), 20 μL Hg 2+ (1×10 -2 M), the absorption spectra of ion-pair probe CPY with different concentrations were measured.

[0075] like figure 2 shown, adding Hg 2+ After that, with Hg 2+ With the increase of concentration, the green fluorescence at 520nm gradually weakened and gradually quenched, and the solution changed from yellow to reddish-brown under sunlight. It can be seen that at 0-150 μM Hg 2+ In the concentration range, the fluorescence intensity of compound CPY has a good linear correlation with the concentration of ions, the linear regression equation y=-5.32324x+829.08382, R 2 =0.98702, calculated as Hg 2+ The detection limit was 14.3 nM.

[0076] like image 3 shown, adding differ...

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Abstract

The invention discloses a dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe as well as a preparation method and application thereof. Dehydroabietic acid is subjected to acylating chlorination, methyl esterification, bromination and double nitration reaction and iron powder reduction to prepare 12-bromine-13-amino de-isopropyl dehydroabietic acid methyl ester, and the 12-bromine-13-amino de-isopropyl dehydroabietic acid methyl ester is subjected to dehydroabietic acid-based Schiff base multi-ion functional fluorescent probe is prepared. The preparation method comprises the following steps: carrying out cyclization reaction on o-phenylenediamine and 5-bromosalicylaldehyde, then carrying out reaction with trifluoroacetic acid to prepare 3-(1H-benzo [d] imidazole-2-yl)-2-hydroxy-5-methylbenzaldehyde, and carrying out reaction on 12-bromo-13-amino de-isopropyldehydroabietic acid methyl ester and the 3-(1H-benzo [d] imidazole-2-yl)-2-hydroxy-5-methylbenzaldehyde to prepare the fluorescent probe. The compound can recognize Hg < 2 + >, Cu < 2 + > and ClO <->, after Cu < 2 + > is added, green fluorescence is gradually weakened until quenching, green fluorescence is gradually weakened, blue fluorescence gradually appears and is gradually enhanced after ClO <-> is added, green fluorescence is gradually weakened and gradually quenched after Hg < 2 + > is added, a solution becomes red brown from yellow under sunlight, and the detection result is accurate.

Description

technical field [0001] The invention belongs to the field of designing fine organic synthesis, and particularly relates to a dehydroabietate-based Schiff base multi-ion functional fluorescent probe and a preparation method and application thereof. Background technique [0002] Mercury ion belongs to a kind of toxic ion, and its existence is harmful to life and health. It is transformed into highly toxic methylmercury through the action of bacteria, which can be enriched in the organism through the food chain. Common diseases include kidney failure, Minamata disease, and motor and neurological disorders. [0003] Copper ions play many important roles in fundamental physiological processes, such as enzyme function, blood formation, respiration, and transcription of biological processes. However, once the homeostasis is lost, it will lead to various diseases, such as coronary heart disease, liver disease, anemia, etc. Hypochlorous acid (HClO) is an important component of reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K11/06G01N21/64
CPCC07D235/18C09K11/06G01N21/6428C09K2211/1011C09K2211/1007C09K2211/1044G01N2021/6432G01N2021/6439Y02P20/55
Inventor 谷文孙露陈霖霖杨子辉孙雪宝金道峻邱遗贵王石发
Owner NANJING FORESTRY UNIV
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