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Gold (III) complex-perylene diimide derivative, and fluorescent sensing tube and tubular fluorescent sensor prepared from same

A perylene diimide and fluorescent sensor technology, which is applied in the field of small molecule fluorescent sensing materials, can solve the problem of unreasonable distribution of the gas flow field of the substance to be detected, the large volume of the gas chamber of the laminated fluorescent sensor, and the reduction of the luminous efficiency of the material and other issues, to achieve excellent photothermal stability, sensing selectivity and sensitivity improvement, and high sensitivity

Active Publication Date: 2021-11-19
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the strong intermolecular stacking effect of perylene diimide, its derivatives are prone to H-aggregation, resulting in a decrease in the luminous efficiency of the material and a decrease in solubility, which in turn affects its practical application.
[0005] Although the laminated fluorescent sensor has the advantages of small size, high signal-to-noise ratio, easy arraying, and can be used for rapid detection of some important chemical substances, the laminated fluorescent sensor also has a large gas chamber volume, and the gas flow of the substance to be detected cannot be detected. Therefore, it is necessary to develop a new type of thin-film fluorescence sensor that has the advantages of high signal-to-noise ratio, small size, high sensitivity, and more reasonable gas flow field.

Method used

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  • Gold (III) complex-perylene diimide derivative, and fluorescent sensing tube and tubular fluorescent sensor prepared from same
  • Gold (III) complex-perylene diimide derivative, and fluorescent sensing tube and tubular fluorescent sensor prepared from same
  • Gold (III) complex-perylene diimide derivative, and fluorescent sensing tube and tubular fluorescent sensor prepared from same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Synthesis of Gold (Ⅲ) Complex-Perylene Diimide Derivatives (In this Example, n=4)

[0101] Among them, p-bromoaniline and 2,6-di(tert-butyl)phenylpyridine are selected as raw materials.

[0102] 1) Synthesis of compound 1-1

[0103]Weigh 1.43g of 2,6-bis(tert-butyl)phenylpyridine and 2.65g of mercuric acetate into a 100mL two-necked bottle, add 40mL of ethanol and reflux at 85°C for 24 hours, then add lithium chloride-methanol solution (0.60g Lithium chloride was dissolved in 10mL of methanol), reacted at 60°C for half an hour, then added 40mL of deionized water to precipitate, filtered, washed with deionized water, and the obtained white solid a was vacuum-dried at 50°C for later use; weighed 308mg of white solid a and 246mg of potassium chloroaurate in a 100mL two-neck bottle. Under nitrogen protection, 45 mL of acetonitrile was added to the reaction system, heated to 80° C., stirred for 24 hours, cooled to room temperature, and spin-dried. A yellow solid compound ...

Embodiment 2

[0122] Synthesis of Gold (Ⅲ) Complex-Perylene Diimide Derivatives (In this Example, n=0)

[0123] Among them, p-bromoaniline and 2,6-diphenylpyridine are selected as raw materials.

[0124] 1) Synthesis of compound 1-2

[0125] Weigh 1.60g of 2,6-diphenylpyridine and 4.4g of mercuric acetate into a 100mL two-necked bottle, add 40mL of ethanol and reflux at 85°C for 24 hours, then add lithium chloride-methanol solution (1.0g of lithium chloride dissolved in 20mL of methanol), react at 60°C for half an hour, add 60mL of deionized water to precipitate precipitate, filter and wash with deionized water, the obtained white solid a is vacuum-dried at 50°C for later use; weigh 308mg of white solid a and 246mg of gold chloride Potassium acid in a 100mL two-neck bottle. Under nitrogen protection, 45 mL of acetonitrile was added to the reaction system, heated to 80° C., stirred for 24 hours, cooled to room temperature, and spin-dried. Using dichloromethane:petroleum ether (1:1) as the...

Embodiment 3

[0143] Synthesis of Gold (Ⅲ) Complex-Perylene Diimide Derivatives (In this Example, n=4)

[0144] Among them, m-bromoaniline and 2,6-di(tert-butyl)phenylpyridine are selected as raw materials.

[0145] 1) Synthesis of compound 1-1

[0146] Weigh 1.43g of 2,6-bis(tert-butyl)phenylpyridine and 2.65g of mercuric acetate into a 100mL two-necked bottle, add 40mL of ethanol and reflux at 85°C for 24 hours, then add lithium chloride-methanol solution (0.60g Lithium chloride was dissolved in 10mL of methanol), reacted at 60°C for half an hour, then added 40mL of deionized water to precipitate, filtered, washed with deionized water, and the obtained white solid a was vacuum-dried at 50°C for later use; weighed 308mg of white solid a and 246mg of potassium chloroaurate in a 100mL two-neck bottle. Under nitrogen protection, 45 mL of acetonitrile was added to the reaction system, heated to 80° C., stirred for 24 hours, cooled to room temperature, and spin-dried. A yellow solid was obta...

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Abstract

The invention provides a gold (III) complex-perylene diimide derivative, and a fluorescent sensing tube and a tubular fluorescent sensor prepared from the same. A flexible rotatable cyclometalated alkynyl group (III) structure with good chemical stability and planar structure characteristics is introduced into a bending position modified perylene diimide anhydride position; the non-planarity of the formed structure effectively inhibits the strong intermolecular accumulation effect of perylene diimide, avoids aggregation-induced fluorescence quenching, and improves the luminous efficiency of perylene diimide; and the cyclometalated Au (III) complex and perylene diimide can also form an ideal energy donor-acceptor pair, so that the apparent Stokes shift of the system is effectively widened, and a foundation is laid for structural optimization of a sensor to be built. The gold (III) complex-perylene diimide derivative has good fluorescence performance, and the tubular fluorescence sensor is high in sensitivity.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescent sensing materials, and in particular relates to a gold (III) complex-perylene diimide derivative and a fluorescent sensing tube and a tubular fluorescent sensor prepared therefrom. Background technique [0002] Residents' diverse needs for interior decoration lead to more and more furniture only focusing on aesthetics, not environmental protection and health. The increasingly serious indoor air pollution will not only cause environmental pollution, but also threaten human health. As the source of disease, formaldehyde is the number one invisible killer that endangers public health indoors, and it is also one of the indicators of public hygiene standards in my country. Formaldehyde, also known as formaldehyde, is a colorless gas, but it has a certain pungent smell and can enter the human body through the respiratory tract. Because formaldehyde has the characteristics of strong a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/12C09K11/06G01N21/64
CPCC07F1/12C09K11/06G01N21/643C09K2211/188
Inventor 房喻张晶刘太宏刘科文瑞娟
Owner SHAANXI NORMAL UNIV
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