Si-rhodamine B thiolactone, preparation method and applications thereof

A technology of thiourea and reaction, applied in the field of Si-rhodamine B lactothioate and its preparation and application, can solve the problems of rare and limited quantity

Inactive Publication Date: 2015-01-07
NAT RESERACH CENT OF GEOANALYSIS +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with the number of fluorescent probes in the ultraviolet-visible region, the number of fluorescent probes in the near-infrared region that can be used for heavy metal ion detection and cell imaging is very limited, especially the near-infrared molecules based on Si-rhodamine Sensors are even rarer

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  • Si-rhodamine B thiolactone, preparation method and applications thereof
  • Si-rhodamine B thiolactone, preparation method and applications thereof
  • Si-rhodamine B thiolactone, preparation method and applications thereof

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Embodiment 1

[0036] Embodiment 1, the preparation of optical sensor molecule Si-RBS

[0037] Experiments have shown that Si-rhodamine B ( figure 1 Chinese formula Ⅱ) to Hg 2+ No fluorescence response, the application carried out the following structural modification on Si-rhodamine B to obtain Hg 2+Fluorescence-responsive Si-rhodamine B lacthione ( figure 1 Chinese formula I), reaction process such as figure 1 As shown, the specific method is as follows: Si-rhodamine B (formula II, 0.40 mmol) was dissolved in 6 mL of 1,2-dichloroethane, and 0.35 mL of phosphorus oxychloride was slowly added dropwise thereto. The mixed system was heated to reflux under stirring for 6h, and then the solvent was evaporated under reduced pressure to obtain the green oily Si-rhodamine B acid chloride ( figure 1 Chinese formula III). The crude product of Si-rhodamine B acid chloride is directly dissolved in 6 mL of tetrahydrofuran without purification to form a tetrahydrofuran solution of Si-rhodamine B aci...

Embodiment 2

[0041] Embodiment 2, Si-RBS is as analysis reagent to Hg 2+ Perform absorbance detection

[0042] 1. Si-RBS to Hg 2+ Sensitivity for Absorbance Detection

[0043] The experiment was repeated three times, and the method of each experiment was as follows: 1 mL of ethanol and 25 μL of Si-RBS ethanol solution (1 mM concentration) were added to each of 11 5 mL test tubes, and then 0, 2.5 , 5.0, 7.5, 10.0, 12.5, 15.0, 17.5, 20.0, 22.5 and 25.0μL Hg 2+ Mother liquor (concentration is the HgCl of 2.0mM 2 Solution), these 11 test tubes were all dilute to 2.5 mL with 0.2M NaAc-HAc buffer solution (pH=5.2), and 11 reaction solutions were obtained. Transfer the reaction solution to a 1cm quartz cuvette at room temperature (20-25°C), and use a mixture of 1mL ethanol and 1.5mL 0.2M NaAc-HAc buffer solution (pH=5.2) as a blank to measure the pH of the reaction system. UV absorption spectrum. At this point, the concentration of Si-RBS in the 11 reaction solutions was 10 μM, Hg 2+ The c...

Embodiment 3

[0046] Embodiment 3, Si-RBS is as analysis reagent to Hg 2+ Perform fluorescence detection

[0047] 1. Solution pH value vs. Hg 2+ Influence of Fluorescence Spectrum of Reaction System with Si-RBS

[0048] The experiment was repeated three times, and each experiment method was as follows: the concentration of preparing pH values ​​of 3.6, 4.0, 4.4, 4.8, 5.2 and 5.6 was 0.2M NaAc-HAc buffer solution and the concentrations of pH values ​​of 6.3, 6.9, 7.4 and 8.0 were respectively 0.2M sodium dihydrogen phosphate-citric acid buffer solution. Add 1 mL ethanol, 25 μL Si-RBS ethanol solution (1 mM concentration) and 25 μL Hg to each of ten 5 mL test tubes. 2+ Mother solution (concentration of 2mM HgCl 2 Solution), these 10 test tubes were all dilute to 2.5mL with the above-mentioned buffer solutions with different pH values, and 10 test tubes with pH values ​​of 3.6, 4.0, 4.4, 4.8, 5.2, 5.6, 6.3, 6.9, 7.4 and 8.0 were obtained. The reaction solution. Transfer the reaction solu...

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Abstract

The invention discloses a Si-rhodamine B derivative, a preparation method and applications thereof. The provided Si-rhodamine B derivative is Si-rhodamine B thiolactone (Si-RBS for short), and is represented by the structural formula I. The Si-rhodamine thiolactone solution is colorless and fluorescent, and is capable of selectively carrying out color developing and fluorescence triggering reactions with Hg2+. Furthermore, a system with an excellent optical performance can be formed in the colorless solution, and thus the sensitivity and selectivity of Hg2+ detection are both greatly improved. So Si-rhodamine B thiolactone can be used to carry out high sensitive and high selective detection on Hg2+, and the detection can be performed in a mode of absorption spectrum or fluorescence spectrum.

Description

technical field [0001] The invention relates to a Si-rhodamine B derivative in the field of chemistry and its preparation method and application, in particular to Si-rhodamine B lacthione, its preparation method and its application in detecting Hg(II). Background technique [0002] Optical sensors suitable for heavy metal ion detection or biological imaging stand out from many detection methods due to their high sensitivity, high selectivity, and the ability to achieve non-destructive detection of organisms. They have become an important branch of molecular fluorescence research today. Fields such as ion detection, fluorescent immunoassay and cell imaging show broad application prospects. Rhodamine B, as a fluorescent matrix with excellent performance, has been widely used in the design and synthesis of optical sensor molecules, such as Lee et al. (Chem. Fluorescent parent Fe 3+ Optical sensor; Swamy et al. (Chemical Communications, 2008, 45:5915-5917) constructed a monobo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C09K11/06G01N21/64G01N21/33
Inventor 王晓春陈新启樊兴涛
Owner NAT RESERACH CENT OF GEOANALYSIS
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