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Fluorescence sensing material based on rhodamine B and hydroxy-4-biphenylcarbonitrile, and preparation and application thereof

A cyanobiphenol and fluorescent sensing technology, which is applied in the field of chemical fluorescent sensing materials, can solve the problems of expensive detection instruments, many interference factors of detection results, complex operation restrictions, etc., and achieve low preparation costs, good optical properties, The effect of multiple binding sites

Inactive Publication Date: 2018-02-27
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional detection techniques such as atomic absorption spectrophotometry, flame atomization and inductively coupled plasma atomic emission spectrometry require complex pretreatment of samples before detection, and there are many interference factors in the detection results. In addition, the detection equipment is expensive , the complex operation limits its general application

Method used

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  • Fluorescence sensing material based on rhodamine B and hydroxy-4-biphenylcarbonitrile, and preparation and application thereof
  • Fluorescence sensing material based on rhodamine B and hydroxy-4-biphenylcarbonitrile, and preparation and application thereof
  • Fluorescence sensing material based on rhodamine B and hydroxy-4-biphenylcarbonitrile, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] S1. Synthesis of rhodamine ethylenediamine: put 1g (2mmol) rhodamine B in a 100mL round bottom flask, dissolve it completely with 20mL absolute ethanol, and add 0.18g (3mmol) ethylenediamine dropwise while stirring , placed in a 60°C oil bath and stirred at reflux for 8h. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure to obtain a crude product of rhodamine amide, which was recrystallized and purified with absolute ethanol to obtain a pale pink product.

[0037] S2. Preparation of 3-formyl-4-hydroxy-4-biphenyl cyanide: Dissolve 0.39g (2mmol) 4-hydroxy-4-biphenyl cyanide and 1.41g (10mmol) urotropine in 30 mL In glacial acetic acid, place in a 100mL round-bottomed flask and stir to reflux in an oil bath at 90°C. After the reaction is finished, cool to room temperature, add 80 mL of 10M hydrochloric acid solution, stir at room temperature for acidification for 1 h, then extract with dichloromethane, ...

Embodiment 2

[0040] S1. Synthesis of rhodamine ethylenediamine: put 1.44g (3mmol) rhodamine B in a 100mL round bottom flask, dissolve it completely with 30mL of absolute ethanol, and add 0.27g (4.5mmol) of rhodamine B dropwise while stirring. Diamine, placed in a 65°C oil bath, stirred and refluxed for 10h. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure to obtain a crude rhodamine diamide product, which was recrystallized and purified with absolute ethanol to obtain a pale pink product.

[0041] S2. Preparation of 3-formyl-4-hydroxy-4-biphenyl cyanide: Dissolve 0.59g (3mmol) 4-hydroxy-4-biphenyl cyanide and 2.11g (15mmol) urotropine in 50 mL In glacial acetic acid, place in a 100mL round-bottomed flask and stir to reflux in an oil bath at 100°C. After the reaction was completed, cool to room temperature, add 100mL of 10M hydrochloric acid solution and stir at room temperature for acidification for 1 h, then extract w...

Embodiment 3

[0044] S1. Synthesis of rhodamine ethylenediamine: put 2.4g (5mmol) Rhodamine B in a 100mL round bottom flask, dissolve it completely with 40mL of absolute ethanol, add 0.36g (6mmol) of Rhodamine B dropwise while stirring Diamine, placed in a 70°C oil bath, stirred and refluxed for 12h. After the reaction was completed, it was cooled to room temperature, and the solvent was removed under reduced pressure to obtain a crude rhodamine diamide product, which was recrystallized and purified with absolute ethanol to obtain a pale pink product.

[0045] S2. Preparation of 3-formyl-4-hydroxy-4-biphenyl cyanide: Dissolve 0.78g (4mmol) 4-hydroxy-4-biphenyl cyanide and 2.82g (20mmol) urotropine in 70 mL In glacial acetic acid, place in a 100mL round bottom flask and stir to reflux in an oil bath at 110°C. After the reaction is finished, cool to room temperature, add 120mL of 10M hydrochloric acid solution, stir at room temperature for acidification for 1 h, then extract with dichloromet...

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Abstract

The invention relates to a fluorescence sensing material based on rhodamine B and hydroxy-4-biphenylcarbonitrile, and a preparation method and application thereof, and belongs to the technical fieldsof a fluorescence chemical sensing material and chemical analysis and detection. The preparation method comprises the following steps: dissolving rhodamine diethylenediamine and 3-formyl-4-hydroxy-4-biphenylcarbonitrile into absolute ethanol, adding a proper amount of glacial acetic acid, stirring and refluxing in an oil bath pot, cooling to room temperature after the reaction, reducing pressure and removing the solvent to obtain a crude product, and performing recrystallization in ethanol to obtain the fluorescence sensing material. The fluorescence sensing material prepared by the method hasmultiple responsiveness on four metal ions such as Zn<2+>, Al<3+>, Fe<3+> and Cr<3+>, can realize effective detection on the trace amount of the target metal ions in the environment water sample wellby taking out different fluorescence signals, and has the characteristics of easily available raw materials, simple preparation process, high product stability, high detection sensitivity and the like.

Description

technical field [0001] The invention relates to a chemical fluorescent sensing material, in particular to a fluorescent sensing material based on rhodamine B and cyanobiphenol and its preparation method and application, belonging to the technical field of fluorescent chemical sensing materials and chemical analysis and detection. Background technique [0002] With the rapid development of social economy, the ensuing environmental pollution has always been a hot spot that people pay attention to. As one of the pollutants, heavy metal ions are extremely harmful to the environment. The main manifestation is that heavy metal pollutants cannot be degraded by microorganisms in the natural environment, but can only change in form, and their toxicity is not fundamental in this process. Elimination; easily absorbed by organisms, different forms of heavy metal ions will act on animals and plants through biological migration, enrichment, etc., and finally enter the human body through t...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643
Inventor 唐旭王赟李静韩娟李程王蕾倪良
Owner JIANGSU UNIV
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