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Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof

A technology of triethylenetetramine and phenylthiourea, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of difficult synthesis, undetectable, poor selectivity, etc., and achieve a simple and easy synthesis method , Improve the detection sensitivity, improve the effect of selectivity

Active Publication Date: 2014-11-12
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, reported Hg 2+ Most fluorescent probes are a probe molecule combined with a Hg 2+ , and some fluorescent probes for Hg 2+ Some have poor selectivity and low sensitivity; some have good selectivity and high sensitivity, but poor water solubility, and cannot be detected in the aqueous phase; or some have good selectivity and high sensitivity, but are difficult to synthesize

Method used

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  • Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof
  • Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof
  • Fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment one: Hg 2+ Preparation of probe RTTU.

[0034] Using ethanol as a solvent, dissolve 0.5 g (1.05 mmol) rhodamine B in ethanol, then add 1.57 mL (10.5 mmol) triethylenetetramine dropwise, heat to 80°C for 24 h, stop the reaction, and evaporate by rotary evaporation CH 2 Cl 2 and H 2 O extracted 3 times, the organic layer was collected, and the CH was removed by rotary evaporation 2 Cl 2 , to obtain RTTA as a yellow solid. The yield was 86.6%.

[0035] Dissolve 0.1 g (0.175 mmol) of intermediate RTTA and 124.5 μL (1.05 mmol) of phenyl isothiocyanate in acetonitrile, stir the reaction at 80 °C for 48 h, cool to 20 °C, and precipitate a white solid. Stir for 2 h, let stand for 12 h, filter, wash with acetonitrile, and dry to obtain a white powder product, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RTTU with a yield of 19.5%.

[0036] IR (KBr) cm -1 : 3245(NH), 1616, 1544, 1515 (ArH), 2969, 2929 (CH 3 , CH 2 ), 1675 (C=O), 1379, 1450 (...

Embodiment 2

[0038] Embodiment two: Hg 2+ Preparation of probe RTTU.

[0039] Using ethanol as a solvent, dissolve 0.5 g (1.05 mmol) rhodamine B in ethanol, then add 1.88 mL (12.6 mmol) triethylenetetramine dropwise, heat to 70°C for 30 h, stop the reaction, and evaporate by rotary evaporation CH 2 Cl 2 and H 2 O extracted 3 times, the organic layer was collected, and the CH was removed by rotary evaporation 2 Cl 2 , to obtain RTTA as a yellow solid. The yield was 84.3%.

[0040] Dissolve 0.1 g (0.175 mmol) of intermediate RTTA and 207.5 μL (1.75 mmol) of phenyl isothiocyanate in acetonitrile, stir the reaction at 70 °C for 72 h, cool to 20 °C, and precipitate a white solid. Stir for 2 h, let stand for 2 days, filter, wash with acetonitrile, and dry to obtain a white powder product, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RTTU with a yield of 23.3%.

Embodiment 3

[0041] Embodiment three: Hg 2+ Preparation of probe RTTU.

[0042] Using isopropanol as solvent, dissolve 0.5 g (1.05 mmol) rhodamine B in isopropanol, then add 1.88 mL (12.6 mmol) triethylenetetramine dropwise, heat to 80°C for 24 h, stop Reaction, after removal of solvent by rotary evaporation, CH 2 Cl 2 and H 2 O extracted 3 times, the organic layer was collected, and the CH was removed by rotary evaporation 2 Cl 2 , to obtain RTTA as a yellow solid. The yield was 76.9%.

[0043] Dissolve 0.1 g (0.175 mmol) of intermediate RTTA and 249 μL (2.1 mmol) of phenyl isothiocyanate in tetrahydrofuran, stir the reaction at 60 °C for 72 h, cool to 20 °C, and precipitate a white solid. Stir for 2 h, let stand for 12 h, filter, wash with acetonitrile, and dry to obtain a white powder product, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RTTU with a yield of 32.0%.

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Abstract

The invention discloses a fluorescent probe synthesized by rhodamine B, triethylene tetramine and phenyl isothiocyanate and a preparing method and application thereof. Specifically, firstly, the rhodamine B reacts with the triethylene tetramine to form a spirocyclic amide structure which is stable in property, nitrogenous bridged segments are introduced in, and the rhodamine B reacts with the phenyl isothiocyanate, so that sulphur atoms are introduced in. By means of the thiophil property of mercury ions, each molecule in an obtained novel rhodamine B-phenylthiourea derivative RTTU can be combined with three mercury ions, and therefore high selectivity and detection sensitivity are achieved. Fluorescent probe molecules can conduct detection in a neutral buffer solution, especially an aqueous phase and can also detect the mercury ions from mercuric chloride, and higher practicability is achieved. In addition, the fluorescent probe molecules can be directly precipitated out in the preparing process, further separation and purification are not needed, and the synthesizing method is simple and convenient and easy to implement.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a rhodamine B-phenylthiourea derivative used as a mercury ion fluorescent probe material and a preparation method and application thereof. Background technique [0002] Mercury is a heavy metal with the highest occurrence frequency and toxicity, with a wide range of influence and strong toxicity. Due to its high affinity for thiol groups in functional proteins and enzymes, mercury or its derivatives often lead to cellular dysfunction and subsequent health problems (see M. Harada, Minamata disease: methylmercury poisoning in Japan caused by environmental pollution, Crit. Rev. Toxicol. , 1962, 2:40-57). Unfortunately, mercury contamination can occur in a range of natural and man-made environments, such as tsunamis or volcanic eruptions, gold mining, and fuel oil waste. Therefore, effective detection or monitoring of mercury in biological samples or environmental samp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1088G01N21/64
Inventor 徐冬梅洪苗苗刘爱风
Owner HUAWEI TEHCHNOLOGIES CO LTD
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