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Tanshinone benzimidazole fluorescent probe for detecting ClO <-> ions as well as preparation method and application of tanshinone benzimidazole fluorescent probe

A technology of benzimidazole-based fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of improved fluorescence performance, abundant resources, and easy operation

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

AI Technical Summary

Problems solved by technology

So far, people have studied many organic fluorescent probes for detecting ions, for example, β-pinene derivative fluorescent probes, phenanthrenequinone fluorescent probes, borate fluorescent probes to detect hypochlorite ions, However, there is no report on the synthesis of tanshinone benzimidazole-type fluorescent probes for the detection of hypochlorite.

Method used

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  • Tanshinone benzimidazole fluorescent probe for detecting ClO &lt;-&gt; ions as well as preparation method and application of tanshinone benzimidazole fluorescent probe
  • Tanshinone benzimidazole fluorescent probe for detecting ClO &lt;-&gt; ions as well as preparation method and application of tanshinone benzimidazole fluorescent probe
  • Tanshinone benzimidazole fluorescent probe for detecting ClO &lt;-&gt; ions as well as preparation method and application of tanshinone benzimidazole fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthetic method of tanshinone benzimidazole compound, synthetic process is:

[0031]

[0032] Specific steps are as follows:

[0033] 1) 4-(1,6,6-trimethyl-7,8,9,12-tetrahydro-6H-furo[2′,3′:1,2]phenanthrene[3,4-d]imidazole -11-yl) preparation of benzaldehyde (II):

[0034] Accurately weigh 201 mg of terephthalaldehyde and 346 mg of ammonium acetate, add them to a three-necked flask, then add 5 ml of acetic acid and stir to dissolve, accurately weigh 147 mg of tanshinone IIa, add 4 mL of acetic acid to dissolve it, add it to the dropping funnel, and use the dropping funnel Slowly add the acetic acid solution of tanshinone IIa into the three-necked flask, react at 125°C for 50 minutes, neutralize the precipitated solid with saturated aqueous sodium bicarbonate solution, filter with suction, and use petroleum ether: ethyl acetate = 300: 1 ~ 5: 1 was purified by column to obtain yellow solid compound 4-(1,6,6-trimethyl-7,8,9,12-tetrahydro-6H-furo[2′,3′:1,2]phenant...

Embodiment 2

[0039] Accurately weigh 5 mg of the fluorescent probe TPD and dissolve it in absolute ethanol to make 1×10 -3 M solution, take 100 μM stock solution and dilute it with ethanol aqueous solution (ethanol: water = 3: 7, pH = 7) to 10 mL concentration of 1 × 10 -5 M solution, followed by the addition of equimolar amounts of ClO - , SO 3 2- , NO 3 - , Cl - , NO 2 - , HCO 3 - , I - , H 2 PO 4 - , OAc - , HPO 4 2- , SCN - , Na + , Cu 2+ , Cd 2+ , La 3 + ,Co 2+ , K + , In 3+ , NH 4 + , pb 2+ , Hg 2+ Plasma, record the fluorescence spectrum of the solution. like figure 1 As shown, the fluorescence intensity of the fluorescent probe TPD does not change much when other ions are added, but when ClO is added - When the fluorescence intensity rose sharply, adding ClO - The post-ion solution showed a very obvious fluorescence enhancement phenomenon. Description of the compound as a detection ClO - Fluorescence-enhanced probes for ions with excellent selectiv...

Embodiment 3

[0041] The fluorescent probe TPD was dissolved in aqueous ethanol (ethanol:water=3:7) (1×10 -5 M), add (0~100)×10 -5 MClO - , measured by adding different concentrations of ClO - 2-Amino-3-(((E)-4-(1,6,6-trimethyl-7,8,9,12-tetrahydro-6H-furan[2′,3′:1,2 ]phenanthrene[3,4-d]imidazol-11-yl)benzylidene)amino)maleonitrile fluorescence emission spectrum, such as figure 2 As shown, adding different concentrations of ClO - The fluorescence emission spectrum of the compound with ClO - With the addition of , the fluorescence gradually increases, indicating that the compound can interact with ClO - react.

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Abstract

The invention discloses a tanshinone benzimidazole fluorescent probe for detecting ClO <-> ions as well as a preparation method and application of the tanshinone benzimidazole fluorescent probe, and belongs to the technical field of fine organic synthesis. 4-(1, 6, 6-trimethyl-7, 8, 9, 12-tetrahydro-6H-furan [2 ', 3': 1, 2] phenanthro [3, 4-d] imidazole-11-yl) benzaldehyde is prepared through direct condensation reaction of tanshinone IIa with terephthalaldehyde and ammonium acetate, then the 4-(1, 6, 6-trimethyl-7, 8, 9, 12-tetrahydro-6H-furan [2 ', 3': 1, 2] phenanthro [3, 4-d] imidazole-11-yl) benzaldehyde reacts with 2, 3-diamino-2-butene dinitrile to synthesize 2-amino-3-(((E)-4-(1, 6, 6-trimethyl-7, 8, 9, 12-tetrahydro-6H-furan [2 ', 3': 1, 2] The compound is (2R, 3R, 4R, 4R, 4d) imidazole-11-yl) benzylidene) amino) maleic nitrile. Benzimidazolyl and diaminomaleonitrile Schiff base groups are introduced into the probe, the probe can selectively react with ClO <->, fluorescence is enhanced, and the detection result is accurate.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, in particular to a method for detecting ClO - Ionic tanshinone benzimidazole type fluorescent probe and its preparation method and application. Background technique [0002] Hypochlorous acid (HClO) is an important oxidizing agent that kills bacteria in water, so it is widely used in household bleaches and disinfectants for swimming pools and drinking water. In biological systems, hypochlorous acid is produced by hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase (MPO). It plays an important role in the organism's innate immune response and signal transduction. However, excess HClO in the body can damage cells, oxidize biomolecules, and importantly, it can cause various diseases. Therefore, it is of great significance to develop effective methods for the detection of HClO. [0003] In the detection of hypochlorite, traditional methods such as chromatogra...

Claims

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Application Information

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IPC IPC(8): C07D491/048C09K11/06G01N21/64
CPCC07D491/048C09K11/06G01N21/6428G01N21/643C09K2211/1007C09K2211/1048
Inventor 谷文陈霖霖王忠龙杨子辉刘青松孙月孙雪宝孙露王石发
Owner NANJING FORESTRY UNIV
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