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Nopinyl indazole silver ion fluorescent probe and preparation method thereof

A technology of nopinyl indazoles and silver ions, applied in the field of fine organic synthesis

Active Publication Date: 2022-03-29
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no information on the application of nopinyl indazoles to Ag + detection report

Method used

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  • Nopinyl indazole silver ion fluorescent probe and preparation method thereof
  • Nopinyl indazole silver ion fluorescent probe and preparation method thereof
  • Nopinyl indazole silver ion fluorescent probe and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation process of the Novol-carbazole compound is:

[0028]

[0029] Specific steps are as follows:

[0030] 1) Preparation of 3- (2'-pyridyl) nobil:

[0031] 0.06 mol sodium hydride was added to three flasks equipped with a stirrer, a thermometer and reflow condenser, and 8 ml of glycol dimethyl ether was slowly injected under nitrogen protection, and 0.02 mol nobil is dissolved in 9 ml of glycol dimethyl ether. In the case of slow injection into the flask, the temperature rise control reaction temperature at 82 ° C, heat reflow 0.5 h, 0.024 mol pyridyl hydrochloride is dissolved in 9 ml of glycol dimethyl ether after nitrogen protection under nitrogen protection under nitrogen protection, thin layer chromatography tracking Process, reaction 7-8h. The reaction solution was extracted 3 times with 100 mL of ethyl acetate, combined with a organic phase, washed with saturated brine to neutral, and the organism was dried over anhydrous sodium sulfate, filtered, conce...

Embodiment 2

[0035] Solid 6,6-dimethyl-2-phenyl-3- (2'-pyridyl) -4,5,6,7-tetrahydro-2H-5, 7-bridge-methylhydrazole and different Metal ions are dissolved in 4-hydroxyethylpiperazine (HEPES) buffer solution (20 mM, pH = 7.2, 7 / 3 (v / v) ethanol / water), formulated into a probe compound concentration of 1 × 10 -6 M and AG + All concentration is 1 × 10 -5 The 19 solutions of M. The fluorescence intensity changes in different metal ions were measured under conditions of excitation wavelength of 320 nm, such as figure 1 Indicated. The results show that compounds are Ag + It has strong fluorescence enhanced, maximum absorption wavelength is transferred from 455 nm to 505 nm, and the fluorescent color under UV lamp is turned green, indicating that the compound is ag + Has good selectivity.

Embodiment 3

[0037] Penaged 6,6-dimethyl-2-phenyl-3- (2'-pyridyl) -4,5,6,7-tetrahydro-2H-5, 7-bridge-methylhydrazole (1 × 10 -6 M) + AG + (1 × 10 -5 M) solution (HEPES buffer, 10 mM, pH = 7.2, 50% (v / v) c 2 Hide 5 Add and AG in OH) + Wait molaron K + NA + Mg 2+ , Fe 2+ , Fe 3+ Mn 2+ CA 2+ Al 3+ , PB 2+ , Cr 2+ , CO 2+ , Zn 2+ , BI 3 + Ni 2+ , PB 2+ Cu 2+ SN 2+ , Ba 2+ AG + The fluorescence spectrum was measured under conditions of excitation wavelength of 320 nm. figure 2 Indicated. When other metal ions are added, 6,6-dimethyl-2-phenyl-3- (2'-pyridyl) -4, 5, 6, 7-tetrahydro-2H-5, 7-bridge Cantazole-AG + The fluorescence intensity of the complex has not been affected, indicating that other metal ions have not been detected by compounds. + Result in an impact.

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Abstract

The invention discloses a nopinyl indazole silver ion fluorescent probe and a preparation method thereof. The present invention utilizes the natural renewable resource β-pinene derivative nopinone as a raw material, and nopinone and 2-picolinate methyl ester undergo Claisen condensation reaction to prepare 3-(2'-pyridineformyl)nopine Ketone; 3‑(2′‑pyridineformyl) nopinone is cyclized with phenylhydrazine to obtain the nopinyl indazole compound 6,6‑dimethyl‑2‑phenyl‑3‑(2′ -pyridyl)-4,5,6,7-tetrahydro-2H-5,7-methanoindazole. The compound has a good application in the detection of silver ions as a specific fluorescent probe molecule.

Description

Technical field [0001] In the field of fine organic synthesis, the present invention relates to northane peracantine fluorescence probe molecules and preparation methods thereof and applications in detecting silver ions. Background technique [0002] The silver-containing compound is used as an extensive distribution of resources to many industrial production activities, such as metallurgical industries, pharmaceutical industries, electroplating industries, and food industries. Each year, industrial sewage containing a large number of silver ions flows into the river lake, while low concentrations of silver ions are accumulated in marine organisms, causing harm to humans as the top of the food chain. Silver ions have a serious impact on human nervous system, liver, and bones, causing many diseases. Therefore silver ions are set to have the highest toxicity of metal ions. Therefore, the development of high selectivity, high sensitivity, high-sensitivity AG + The method is of great...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06G01N21/643C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 王石发姜倩徐徐李明新杨益琴王芸芸谷文徐海军卞天岑
Owner NANJING FORESTRY UNIV
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