Fluorescent probe made of rhodamine B, diethylenetriamine and PITC (phenyl isothiocyanate) as well as preparation method and application thereof

A technology of diethylenetriamine and phenylthiourea, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of inability to detect, low sensitivity, poor selectivity, etc., and achieve good practicability , improve the detection sensitivity, improve the effect of selectivity

Inactive Publication Date: 2014-10-15
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 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 made of rhodamine B, diethylenetriamine and PITC (phenyl isothiocyanate) as well as preparation method and application thereof
  • Fluorescent probe made of rhodamine B, diethylenetriamine and PITC (phenyl isothiocyanate) as well as preparation method and application thereof
  • Fluorescent probe made of rhodamine B, diethylenetriamine and PITC (phenyl isothiocyanate) as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0034] Using ethanol as solvent, dissolve 1 g (2.09 mmol) rhodamine B in ethanol, then add 1.57 mL (14.63 mmol) diethylenetriamine dropwise, heat to 81°C for 3 h, stop the reaction, and cool To room temperature, the solvent was removed by rotary evaporation, then washed twice with deionized water, and filtered to obtain a khaki solid powder, which was the spirocyclic amide intermediate RDTA, with a yield of 94.8%.

[0035] Dissolve 0.2 g (0.36 mmol) of the intermediate RDTA and 85.4 μL (0.72 mmol) of phenyl isothiocyanate in acetonitrile, heat to 50 °C for 6 h, cool to room temperature, remove the solvent by rotary evaporation, separate on a silica gel column, wash The removal agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 2), and a white solid powder is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RDTU with a yield of 30.1%.

[0036] IR (KBr) cm -1 : 3413 (NH), 2968, 2926 ...

Embodiment 2

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

[0039] Using methanol as a solvent, dissolve 1 g (2.09 mmol) rhodamine B in methanol, then add 1.12 mL (10.45 mmol) diethylenetriamine dropwise, heat to 65 °C for 10 h, stop the reaction, and cool to At room temperature, the solvent was removed by rotary evaporation, then washed twice with deionized water, and filtered to obtain a khaki solid powder, which was the spirocyclic amide intermediate RDTA, with a yield of 45.7%.

[0040] Dissolve 0.2 g (0.36 mmol) of the intermediate RDTA and 170.8 μL (1.44 mmol) of phenyl isothiocyanate in tetrahydrofuran, heat to 50 °C for 6 h, cool to room temperature, remove the solvent by rotary evaporation, separate on a silica gel column, wash The removal agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 2), and a white solid powder is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RDTU, yield: 38.1%.

Embodiment 3

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

[0042] With isopropanol as solvent, 1 g (2.09 mmol) rhodamine B was dissolved in isopropanol, then 1.79 mL (16.72 mmol) diethylenetriamine was added dropwise, heated to 82 °C for 8 h, Stop the reaction, cool to room temperature, remove the solvent by rotary evaporation, then wash twice with deionized water, and filter to obtain a khaki solid powder, which is the spirocyclic amide intermediate RDTA, with a yield of 82.5%.

[0043] Dissolve 0.2 g (0.36 mmol) of the intermediate RDTA and 170.8 μL (1.44 mmol) of phenyl isothiocyanate in acetonitrile, heat to 50 °C for 4 h, cool to room temperature, remove the solvent by rotary evaporation, separate on a silica gel column, wash The removal agent is a mixture of ethyl acetate and petroleum ether (v / v, 1 / 2), and a white solid powder is obtained, which is rhodamine B-phenylthiourea derivative (Hg 2+ probe) RDTU, yield: 46.6%.

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Abstract

The invention discloses a fluorescent probe made of rhodamine B, diethylenetriamine and PITC (phenyl isothiocyanate) as well as a preparation method and an application thereof. Specifically, rhodamine B and diethylenetriamine react firstly to form a spiro amide structure with a stable property, a nitrogen bridging fragment is introduced, and the mixture then reacts with PITC so as to introduce a sulfur atom. By means of sulphophile affinity of mercury ions, each molecule of a novel rhodamine B-phenylthiourea derivative (namely, mercury ion fluorescent probe RDTU) obtained through the scheme can be combined with two mercury ions, so that the fluorescent probe has higher selectivity and detection sensitivity. The molecules of the fluorescent probe can perform detection in a neutral buffer solution especially in water phase. Additionally, the molecules of the fluorescent probe can detect the mercury ions from mercury chloride, and has better practicability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a rhodamine B-phenylthiourea derivative used as a 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 samples has becom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 徐冬梅刘爱风洪苗苗
Owner SUZHOU UNIV
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