Fluorescence probe based on RB (rhodamine B), TEPA (tetraethylenepentamine) and PITC (phenyl isothiocyanate) as well as preparation method and application of fluorescence probe

A technology of tetraethylenepentamine and phenylthiourea, which is applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of inability to detect, poor selectivity, poor water solubility, etc., to improve detection sensitivity, Good practicability and the effect of improving selectivity

Active Publication Date: 2014-10-15
HUAWEI TEHCHNOLOGIES CO LTD
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  • 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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  • Fluorescence probe based on RB (rhodamine B), TEPA (tetraethylenepentamine) and PITC (phenyl isothiocyanate) as well as preparation method and application of fluorescence probe
  • Fluorescence probe based on RB (rhodamine B), TEPA (tetraethylenepentamine) and PITC (phenyl isothiocyanate) as well as preparation method and application of fluorescence probe
  • Fluorescence probe based on RB (rhodamine B), TEPA (tetraethylenepentamine) and PITC (phenyl isothiocyanate) as well as preparation method and application of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment one: Hg 2+ Preparation of probe RPTU.

[0033] Using ethanol as a solvent, dissolve 0.2 g (0.42 mmol) rhodamine B in ethanol, then add 956 μL (5.04 mmol) tetraethylenepentamine dropwise, heat to 80°C for 12 h, stop the reaction, and use The solvent was removed by a rotary evaporator, washed three times with water, and dried to obtain a yellow solid, which is the intermediate RTPA. The yield was 90.8%.

[0034] Dissolve 50 mg (0.081 mmol) of intermediate RTPA and 76.8 μL (0.648 mmol) of phenyl isothiocyanate in anhydrous tetrahydrofuran, stir the reaction at 60 °C for 6 h, remove the solvent by rotary evaporation, separate on a silica gel column, and elute The agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 5), and a white powder product is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RPTU with a yield of 13.6%.

[0035] IR (KBr) cm -1 : 3460, 3209 (NH), 2924, 2854 (CH 3 , CH 2 ), 1639 (C=O), 1601, 1543, 1493 (A...

Embodiment 2

[0037] Embodiment two: Hg 2+ Preparation of probe RPTU.

[0038] With isopropanol as solvent, 0.2 g (0.42 mmol) Rhodamine B was dissolved in isopropanol, then 796.7 μL (4.2 mmol) tetraethylenepentamine was added dropwise, heated to 80 °C for 10 h, Stop the reaction, remove the solvent with a rotary evaporator, wash with water three times, and dry to obtain a yellow solid, which is the intermediate RTPA. The yield was 81.9%.

[0039] Dissolve 50 mg (0.081 mmol) of intermediate RTPA and 96.0 μL (0.81 mmol) of phenylisothiocyanate in anhydrous acetonitrile, stir the reaction at 20 °C for 6 h, remove the solvent by rotary evaporation, separate on a silica gel column, and elute The agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 5), and a white powder product is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RPTU with a yield of 21.8%.

Embodiment 3

[0040] Embodiment three: Hg 2+ Preparation of probe RPTU.

[0041] With n-butanol as solvent, 0.2 g (0.42 mmol) rhodamine B was dissolved in n-butanol, then 1.2 mL (6.3 mmol) tetraethylenepentamine was added dropwise, heated to 90°C for 10 h, Stop the reaction, remove the solvent with a rotary evaporator, wash with water three times, and dry to obtain a yellow solid, which is the intermediate RTPA. The yield was 78.2%.

[0042] Dissolve 50 mg (0.081 mmol) of intermediate RTPA and 115.2 μL (0.972 mmol) of phenylisothiocyanate in anhydrous acetonitrile, stir the reaction at 30 °C for 6 h, remove the solvent by rotary evaporation, separate on a silica gel column, and elute The agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 5), and a white powder product is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RPTU with a yield of 36.2%.

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Abstract

The invention discloses a fluorescence probe based on RB (rhodamine B), TEPA (tetraethylenepentamine) and PITC (phenyl isothiocyanate) as well as a preparation method and an application of the fluorescence probe. The preparation method comprises specific steps as follows: RB and TEPA react firstly to form a spiro amide structure with a stable property, a nitrogenous bridged fragment is introduced, and the mixture reacts with PITC to introduce sulfur atoms. By virtue of thiophilicity of mercuric ions, each molecule of a novel RB-phenylthiourea derivative RPTU obtained through the scheme can be bound with four mercuric ions, so that higher selectivity and detection sensitivity are achieved; and the fluorescence probe molecules can perform detection in a neutral buffer solution particularly an aqueous phase, can be further used for detecting the mercuric ions of mercuric chloride, and has better practicability.

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 and mercury salts are not only widely used in industry, but also come from natural phenomena such as tsunamis and volcanic eruptions. Accumulation will cause great harm to the central nervous system, digestive system and internal organs of the human body, and also have a certain impact on the respiratory system, skin, blood and eyes, so it is currently one of the most concerned environmental pollutants in the world (See P. B. Tchounwou, W. K. Ayensu, N. Ninashvili, Review: environmental exposure to mercury and its toxicopathologic implications for public health, Environmental Toxicology , 2003, 18:149-175). Therefore, effective detection or monitoring of mercury in the environment and living ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/64G01N21/643
Inventor 徐冬梅洪苗苗
Owner HUAWEI TEHCHNOLOGIES CO LTD
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