A kind of small molecule pH fluorescent probe containing rhodamine lactam group and synthesis method

A fluorescent probe and small molecule technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as hydrogen ion fluorescence response interference, and achieve good anti-interference ability

Inactive Publication Date: 2017-01-11
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In addition, most rhodamine lactam compounds will react with some metal ions such as coordination or catalytic decomposition, so the fluorescence response to hydrogen ions is interfered

Method used

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  • A kind of small molecule pH fluorescent probe containing rhodamine lactam group and synthesis method
  • A kind of small molecule pH fluorescent probe containing rhodamine lactam group and synthesis method
  • A kind of small molecule pH fluorescent probe containing rhodamine lactam group and synthesis method

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Experimental program
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Effect test

Embodiment 1

[0023] (1) Synthesis of compound 1:

[0024] Dissolve 2.395g of rhodamine B (5mmol) in 50mL of absolute ethanol, and then add 1.5g of ethylenediamine. The reaction system was stirred at reflux for 6 hours. After the reaction was completed, the solvent was evaporated under reduced pressure, and the remaining solid was dissolved in 200mL of 1mol / L HCl solution, and 1mol / L NaOH solution was added dropwise to pH=9-10. A large amount of solid precipitated, filtered under reduced pressure, washed with water, and then pumped thoroughly. After drying in a vacuum oven, a brick-red solid was obtained, namely compound 1

[0025] (2) Synthesis of pH fluorescent probe:

[0026] In a 50 mL round bottom flask, 0.485 g of compound 1 (1 mmol) dissolved in 15 mL of methanol was added, and then 0.127 g of p-hydroxybenzaldehyde (1 mmol) was added, and the mixture was refluxed for 4 h. After the reaction, the solid was cooled and precipitated, filtered, washed with methanol until the filtrate b...

Embodiment 2

[0029] Draw the fluorescent emission spectrum of the small molecule pH probe containing the rhodamine lactam group obtained in Example 1 at different pHs in the aqueous solution, the concentration is 0.16 mg / mL, the abscissa is pH, and the ordinate is fluorescence intensity. figure 2 .

[0030] It can be seen from the figure that when the probe is at pH=4-6, its fluorescence intensity has a sudden change, and it can be seen that the fluorescence response range is at pH=4-6. And the response interval is relatively narrow, indicating that the probe pair H + The fluorescence response is very sensitive.

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Abstract

The invention relates to a small-molecule pH fluorescent probe containing a rhodamine lactam group. The synthesis method is to react rhodamine with a carboxyl group at the 2-position with ethylenediamine to form a lactam, and then combine it with a formyl group-containing Substance reaction, a small molecule pH fluorescent probe with specific fluorescent response to H+ is synthesized. The pH fluorescent probe has a simple synthesis method, easy purification, and low reaction loss.

Description

technical field [0001] The invention relates to a small molecule pH fluorescent probe containing a rhodamine lactam group and a synthesis method. Background technique [0002] Due to the high sensitivity, high selectivity, fast response, and simple operation of fluorescent probes, the pH value can be monitored in real time. Therefore, fluorescent pH probes provide powerful detection tools for studying the effects of pH changes on physiological activities, and are widely used in analytical chemistry, bioanalytical chemistry, cell biology, and medicine. [0003] There is a lactam spiro ring structure in the rhodamine-based fluorescent probe molecule, and the fluorescence switch is controlled by the switch of the spiro ring. The spiro ring switch of the rhodamine-based probe can also be controlled by the pH value of the solution, and has a very strong response ability , after interacting with specific ions, it can transform from a non-fluorescent and colorless lactam spiro-rin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D491/107
Inventor 戚裕王红霞邵晶周梦超徐雯雯
Owner SUZHOU UNIV OF SCI & TECH
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