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Triphenylamine derivative, preparation method and application thereof, and preparation method of triphenylamine derivative doped film

A technology of triphenylamine and derivatives, which is applied in the field of preparation of triphenylamine derivatives and their doped thin films, can solve the problems of small color difference, low fluorescence quenching rate, and low optical contrast, and achieve large color difference and fluorescence quenching rate. High and simple synthesis method

Active Publication Date: 2017-11-17
HUZHOU TEACHERS COLLEGE
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AI Technical Summary

Problems solved by technology

The above-mentioned organic fluorescent molecules can be divided into two categories for their ability to donate and pull electrons: (1) localized conjugated organic fluorescent molecules, which have high fluorescence quantum efficiency (brightness), but they exist as acid-induced chromic materials The problem of low contrast and small color difference ( Analyst , 2016, 141, 4108–4120; Chem. Commun. , 2013,49, 3878-3880; J. Mater. Chem. C , 2014, 2, 1539–1544; Chem. Commun., 2015, 51, 13830 -13833)
(2) Intramolecular charge transfer fluorescent molecules, which have high sensitivity, but due to the strong charge transfer ability, the fluorescence quantum efficiency is very low, resulting in low optical contrast ( J. Am. Chem. Soc . 2009, 131, 3158–3159, Chem. Commun. , 2014, 50, 1608--1610)
Currently reported detectable protonic acid gas polymers or small molecule doped polymers mainly include poly(N-isopropylacrylamide), poly(siloxane), poly(aniline), ( Sensors and Actuators B , 2010, 150, 764–769 Adv. Funct. Mater. 2016, 26, 5987-5996, Chem.Commun ., 2014, 50, 4251-4254, Sensors and Actuators B , 2008, 130, 842–847), but they all have the problems of small color difference, low fluorescence quenching rate or poor mechanical properties
Another problem is that currently synthesized materials can only detect proton hydrogen through chromaticity difference or fluorescence quenching rate, and there are relatively few reports on molecules with dual display functions of chromaticity difference and fluorescence quenching rate.

Method used

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Effect test

Embodiment 1

[0035] Dissolve the solid powder of triphenylamine derivative (I) in tetrahydrofuran solvent to prepare a concentration of 1×10 -4 mol / L. Then take 0.01 mL and add it to a 10 mL volumetric flask, then add HCl aqueous solution (9.99 m) L with a pH value of 0.98, and test after 3 minutes, the fluorescence of the solution is completely quenched (the quenching rate is greater than 97%). (For details, please see figure 1 a)

Embodiment 2

[0037] Dissolve 0.1 g of solid powder of triphenylamine derivative (I) in 3 mL of tetrahydrofuran solvent to prepare a concentration of 1×10 - 5 mol / L. Then take 0.01 mL and add it to a 10 mL volumetric flask, then add HCl aqueous solution (9.99 m) L with a pH value of 3.34, and test after 3 minutes, the fluorescence intensity of the solution is significantly reduced (the quenching rate is greater than 50%). (For details, please see figure 1 b)

Embodiment 3

[0039] Spread 0.05 g of the triphenylamine derivative solid powder (I) of the present invention on a quartz plate, it is light yellow under natural light, and shows bright green fluorescence under ultraviolet light. After being placed in 10 ppm hydrogen chloride atmosphere for 15 s, its fluorescence became dark red with a quenching rate of 83.4%. The powder also turns deep red under natural light, and the ∆E reaches 18.7. (see attached figure 2 )

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Abstract

The invention discloses a triphenylamine derivative and a triphenylamine derivative doped SEBS film which can realize acid stimulus responsive color and fluorescence changes. The triphenylamine derivative doped SEBS film respectively has the characteristics of high color aberration and high fluorescent quenching rate in the aspect of reversible acid-alkali stimulus responsive color and fluorescence properties; the film has the characteristic of being stretchable, flexible, compressible and restorable in the mechanical property; and the synthesis method of the film is simple, thereby greatly widening the practical application of the reversible acid-stimulating fluorescence change material in a sensing device.

Description

technical field [0001] The invention relates to the technical field of environmental detection, in particular to a preparation method and application of a triphenylamine derivative and a doped film thereof. Background technique [0002] Hydrogen chloride, sulfur dioxide, sulfur trioxide, etc. are common by-products in industry, and direct discharge will cause serious harm to the environment and human health. In addition, this kind of gas will cause acid rain, which is called "the god of death in the air" abroad, and its potential harm is mainly shown as follows: (1) Harm to aquatic systems and terrestrial ecosystems. (2) Corrosion to buildings, machinery and municipal facilities. (3) Effects on the human body. One is that heavy metals such as mercury and lead enter the human body through the food chain, inducing cancer and Alzheimer's disease; the other is that acid mist invades the lungs, inducing pulmonary edema or death; Excessive lipid oxidation leads to an increased ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C09K11/06C09K9/02C08K5/3432C08L53/02C08J5/18G01N21/64
CPCC07D213/57C08J5/18C08J2353/02C08K5/3432C08L2203/16C09K9/02C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029G01N21/6428G01N21/643G01N2021/6432C08L53/025
Inventor 张玉建张棋杨合一漆俊曹枫张诚
Owner HUZHOU TEACHERS COLLEGE
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