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A dual-mode sensor array and its application to distinguish and recognize hydrazine and organic amines

A sensor array and dual-mode technology, applied in the field of small molecule fluorescence sensing, can solve the problems of discrimination and fewer high-performance fluorescent probes, and achieve the effects of enhanced stability, strong discrimination, recognition and detection capabilities, and improved photoelectric properties

Active Publication Date: 2022-02-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the fluorescent probes reported in the literature to recognize hydrazine and organic amines are single-detection hydrazine or organic amines, and there are few high-performance fluorescent probes with dual detection and discrimination capabilities.
That is to say, when most fluorescent probes encounter hydrazine or organic amine, they show an increase or decrease of fluorescence signal at the same wavelength, and the two cannot be qualitatively distinguished, and other auxiliary means are needed for identification

Method used

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  • A dual-mode sensor array and its application to distinguish and recognize hydrazine and organic amines
  • A dual-mode sensor array and its application to distinguish and recognize hydrazine and organic amines
  • A dual-mode sensor array and its application to distinguish and recognize hydrazine and organic amines

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 1. Preparation of dicyanovinyl functionalized oligothiophene derivatives (NA-3T-CN)

[0050] (1) Synthesis of compound 1

[0051] Under nitrogen protection, dark, 0 ℃ and stirring conditions, 3.2g (17.8mmol) N-bromosuccinimide (NBS) was added dropwise to 45mL containing 5.0g (20.0mmol) 2,2′:5 ′,2″-trithiophene in N,N-dimethylformamide (DMF) solution, react at room temperature for 24 hours, after the reaction is completed, pour the reactant into ice water, extract with 100mL dichloromethane, and wash the organic phase with water 3 times, dried over anhydrous sodium sulfate, and rotary evaporated to obtain light yellow solid compound 1, the reaction equation is as follows:

[0052]

[0053] (2) Synthesis of Compound 2-1

[0054] Under the protection of nitrogen, add 0.24g (10.0mmol) new magnesium chips and 0.05g initiator iodine to the three-necked flask equipped with a reflux condenser and a constant pressure dropping funnel, then add 40mL of dissolved 1.54 mL (11....

Embodiment 2

[0076] 1. Preparation of dicyanovinyl functionalized oligothiophene derivatives (3T-CN)

[0077] (1) Synthesis of compound 3-2

[0078] Under nitrogen protection, 0°C and stirring conditions, 1.2mL (13.0mmol) phosphorus oxychloride was slowly added dropwise to 60mL dissolved in 2.48g (10.0mmol) 2,2′:5′,2″-trithiophene After the dropwise addition, heat the reaction solution to 60°C and continue the reaction for 4 hours. After cooling, pour the above reaction solution into 100mL saturated aqueous sodium acetate solution, filter under reduced pressure to obtain a red The solid was washed several times with deionized water, and the crude product was separated by column chromatography using dichloromethane as a developing solvent to obtain red solid compound 3-2 (referred to as 3T-CHO).

[0079] Its reaction equation is as follows:

[0080]

[0081] (2) Synthesis of dicyanovinyl functionalized oligothiophene derivatives

[0082] Add 0.27g (1.0mmol) of compound 3-2, 0.075mL (1...

Embodiment 3

[0088] 1. Preparation of dicyanovinyl functionalized oligothiophene derivatives (4T-CN)

[0089] (1) Synthesis of compound 2-1

[0090] Under the protection of nitrogen, add 0.24g (10.0mmol) new magnesium chips and 0.05g initiator iodine to the three-necked flask equipped with a reflux condenser and a constant pressure dropping funnel, then add 40mL of dissolved 1.54 mL (11.0 mmol) of 1-bromothiophene in tetrahydrofuran was heated to 80° C. and reacted until the magnesium dust disappeared completely to obtain the prepared Grignard reagent.

[0091] Under nitrogen protection, weigh 3.62g (8.0mmol) of compound 1, 0.22g (0.4mmol) of 1,3-bis(diphenylphosphinopropane)nickel dichloride catalyst into a three-necked flask, add 40mL of tetrahydrofuran, and Add the above-prepared Grignard reagent dropwise at 0°C, slowly raise the temperature under stirring, and reflux for 24 hours; after the reaction is completed, cool to room temperature, pour the reaction solution into 150 mL of satu...

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Abstract

The invention discloses a dual-mode sensor array and its application for distinguishing and recognizing hydrazine and organic amines, wherein the fluorescent compounds involved in the dual-mode sensor array are dicyanovinyl functionalized oligothiophene derivatives and zinc porphyrin derivatives . The two types of fluorescent compounds and the mixture solutions of the two are drop-coated on the silica gel plate respectively, and a ratiometric UV-visible and fluorescent dual-mode sensor array is obtained; the output color and signal are brought about by the composite change of the absorption and fluorescence emission peak intensity Changes to achieve specific and selective recognition of target analytes. Before and after adding the analyte, the color change of the dual-mode sensor array is very significant under the fluorescent lamp and the ultraviolet lamp, which weakens the interference of environmental factors, and the result is accurate; at the same time, the response speed is fast, the operation is simple, and it shows that it is sensitive to hydrazine, fat, etc. Amine and aniline target analyte solutions have strong sensitive detection and discrimination and recognition capabilities, and have great development potential and application value.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescence sensing, and in particular relates to a dual-mode sensor array and a sensing application based thereon. Background technique [0002] Hydrazine and organic amine compounds are important chemical raw materials for the synthesis of many pesticides and medicines, and are also important environmental pollutants and highly toxic biochemical reagents, which have the "three effects" of carcinogenicity, teratogenicity, and mutagenicity. Therefore, the development of efficient detection methods for hydrazine and organic amines has very important practical significance for chemical production and environmental protection. Common methods for detecting hydrazine and organic amines include chromatography, spectrophotometry, electrochemical methods, titration methods, etc. These methods generally have problems such as low sensitivity, low selectivity, expensive instruments or complicated ope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/78G01N21/64C07D333/24C07D487/22C09K11/06
CPCG01N21/78G01N21/643C07D333/24C07D487/22C09K11/06C09K2211/188C09K2211/1092C09K2211/1011
Inventor 刘太宏冯婉杨吕洁臧建阳房喻
Owner SHAANXI NORMAL UNIV