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Six-membered spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure as well as preparation method and application of six-membered spiro rhodamine copper ion fluorescent probe

A fluorescent probe and hexa-snail technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of short fluorescence stability time, poor water solubility, strong pH dependence, etc.

Active Publication Date: 2021-07-02
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the five-membered spirolactam part may have poor water solubility, short fluorescence stability time, and strong pH dependence

Method used

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  • Six-membered spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure as well as preparation method and application of six-membered spiro rhodamine copper ion fluorescent probe
  • Six-membered spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure as well as preparation method and application of six-membered spiro rhodamine copper ion fluorescent probe
  • Six-membered spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure as well as preparation method and application of six-membered spiro rhodamine copper ion fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Six-membered spirocyclic rhodamine copper ion fluorescent probe containing hydroxyurea structure——RhB-OH

[0031] The reaction formula is as follows:

[0032]

[0033] In a round bottom flask, mix 1 mol of Rhodamine B and 3 mol of POCl 3 Add it to dry 120mL of 1,2-dichloroethane, react in an oil bath at 90°C for 4h, cool to room temperature, distill off the solvent under reduced pressure, dissolve the obtained solid in 120mL of dry acetonitrile, add 1.3mol of azide Sodium, stir overnight at room temperature, add anhydrous magnesium sulfate to the reaction solution, dry and filter, heat the filtrate at 82°C for 40 minutes to obtain isocyanate, mix the obtained isocyanate solution with a mixture of 3mol hydroxylamine hydrochloride and 3mol triethylamine, and stir at room temperature, After reacting for 60 minutes, the obtained product was distilled and concentrated under reduced pressure to obtain a six-membered spirocyclic rhodamine copper ion fluorescent p...

Embodiment 2

[0034] Example 2 Six-membered spirocyclic rhodamine copper ion fluorescent probe containing hydroxyurea structure——RhTMR-OH

[0035]

[0036] In a round bottom flask, 1 mol of tetramethylrhodamine TMR and 3 mol of POCl 3 Add it to dry 120mL of 1,2-dichloroethane, react in an oil bath at 90°C for 4h, cool to room temperature, distill off the solvent under reduced pressure, dissolve the obtained solid in 120mL of dry acetonitrile, add 1.3mol of azide Sodium, stir overnight at room temperature, add anhydrous magnesium sulfate to the reaction solution, dry and filter, heat the filtrate at 82°C for 40 minutes to obtain isocyanate, mix the obtained isocyanate solution with a mixture of 3 mol hydroxylamine hydrochloride and 3 mol triethylamine, and react for 60 minutes. After the obtained product is concentrated by distillation under reduced pressure, a six-membered spiro-ring rhodamine copper ion fluorescent probe RhTMR-OH containing a hydroxyurea structure is obtained. HRMS: 41...

Embodiment 3

[0037] Example 3 Six-membered spirocyclic rhodamine copper ion fluorescent probe containing hydroxyurea structure——Rh101-OH

[0038]

[0039] In a round bottom flask, 1 mol of Rhodamine 101 and 3 mol of POCl 3 Add it to dry 120mL of 1,2-dichloroethane, react in an oil bath at 90°C for 4h, cool to room temperature, distill off the solvent under reduced pressure, dissolve the obtained solid in 120mL of dry acetonitrile, add 1.3mol of azide Sodium, stir overnight at room temperature, add anhydrous magnesium sulfate to the reaction solution, dry and filter, heat the filtrate at 82°C for 40 minutes to obtain isocyanate, mix the obtained isocyanate solution with a mixture of 3 mol hydroxylamine hydrochloride and 3 mol triethylamine, and react for 60 minutes. The obtained product was distilled and concentrated under reduced pressure to obtain a six-membered spirocyclic rhodamine copper ion fluorescent probe RH101-OH containing a hydroxyurea structure. HRMS: 520.2474.

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Abstract

The invention discloses a six-membered spiro rhodamine copper ion fluorescent probe containing a hydroxyurea structure as well as a preparation method and application of the six-membered spiro rhodamine copper ion fluorescent probe. The six-membered spiro rhodamine copper ion fluorescent probe containing the hydroxyurea structure has a structural general formula as shown in (I). The preparation method comprises the following steps: taking a rhodamine compound, phosphorus oxychloride and dry 1, 2-dichloroethane, reacting at 90 DEG C for 4 hours, cooling to room temperature, carrying out reduced pressure distillation to remove a solvent, dissolving the obtained solid in dry acetonitrile, adding sodium azide, stirring overnight at room temperature, adding a drying agent for drying, filtering, reacting the obtained filtrate at 82 DEG C for 40 minutes, and cooling to room temperature, and adding a mixed solution of hydroxylamine hydrochloride and triethylamine, and reacting to obtain a target product. The fluorescent probe provided by the invention has good sensitivity to copper ions, and can qualitatively and quantitatively detect the copper ions in a solution.

Description

technical field [0001] The invention relates to a six-membered spiro-ring rhodamine copper ion fluorescent probe containing a hydroxyurea structure. Background technique [0002] The fluorescent signal shows fast response time, excellent spatial resolution and high signal-to-noise ratio, and the fluorescent staining has high sensitivity, and has the advantages of no damage to the sample and little damage to the cells under the microscope. Rhodamine fluorescent dyes are widely used as fluorescent probes for the detection of heavy metal ions due to their high absorbance coefficient, broad fluorescence in the visible region, high fluorescence quantum yield, and photostability. In previous studies, almost all rhodamine-based fluorescent probes contained a five-membered spirolactam ring structure, and few rhodamine fluorescent probes were designed and synthesized with six-membered rings. However, the five-membered spirolactam part may have poor water solubility, short fluorescen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C07D491/22C09K11/06G01N21/33G01N21/64
CPCC07D491/107C07D491/22C09K11/06G01N21/6428G01N21/6447G01N21/33G01N2021/6439C09K2211/1048C09K2211/1077
Inventor 于海波雷永胜马明月金家伊程瑜萱于欣艺孙与时刘思言
Owner LIAONING UNIVERSITY
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