Preparation method and application of triphenylamine derivative and doped thin film thereof

A technology for triphenylamine and derivatives, which is applied in the field of triphenylamine derivatives and the preparation of doped films, can solve the problems of small chromatic aberration, low optical contrast, low fluorescence quenching rate and the like, achieves large chromatic aberration, simple synthesis method, The effect of high fluorescence quenching rate

Inactive Publication Date: 2017-06-23
HUZHOU TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned organic fluorescent molecules donating and pulling electrons can be divided into two categories: (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 ,150,764–769Adv.Funct.Mater.2016,26,5987-5996, Chem.Commun.,2014,50,4251-4254,Sensors and Actuators B,2008,130,842–847), but there are small color difference and fluorescence quenching Low extinction 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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  • Preparation method and application of triphenylamine derivative and doped thin film thereof
  • Preparation method and application of triphenylamine derivative and doped thin film thereof
  • Preparation method and application of triphenylamine derivative and doped thin film thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Dissolve the solid powder of triphenylamine derivative (I) in tetrahydrofuran solvent, and prepare the concentration to be 1×10 -4 mol / L. Then take 0.01mL and add it to a 10mL volumetric flask, then add HCl aqueous solution (9.99m) L with a pH value of 0.98, test after 3 minutes, and the solution fluorescence is completely quenched (the quenching rate is greater than 97%). (For details, please see figure 1 a)

Embodiment 2

[0035] Dissolve 0.1 g of triphenylamine derivative (I) solid powder in 3 mL of tetrahydrofuran solvent to prepare a concentration of 1×10 - 5 mol / L. Then get 0.01mL and add it to a 10mL volumetric flask, then add HCl aqueous solution (9.99m) L with a pH value of 3.34, test after 3 minutes, the solution fluorescence intensity is significantly reduced (quenching rate is greater than 50%). (For details, please see figure 1 b)

Embodiment 3

[0037] 0.05 g of the triphenylamine derivative solid powder (I) of the present invention is spread on a quartz plate, and is light yellow under natural light, and shows bright green fluorescence under ultraviolet light. Placed in 10ppm hydrogen chloride atmosphere for 15s, its fluorescence becomes dark red, and the quenching rate is 83.4%. The powder also turns deep red under natural light, and the ΔE reaches 18.7. (see attached figure 2 )

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Abstract

The invention discloses a triphenylamine derivative having acid stimulation response color and fluorescence double change and an SEBS (Styrene-Ethylene/Butadiene-Styrene Copolymer)-doped thin film thereof. The reversible acid-alkali stimulation response color and fluorescence properties of the SEBS-doped thin film of the triphenylamine derivative respectively have the characteristics of large chromatic aberration and high fluorescence quenching rate; the mechanical property of the thin film has the characteristics of tensibility, bending performance, compression performance and restorability; the thin film is simple in synthesis method, and the reality of a reversible acid stimulation fluorescent change material in sensors is greatly broadened.

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 sky" abroad, and its potential harm is mainly shown in the following: (1) Harm to aquatic systems and terrestrial ecosystems. (2) Corrosion to buildings, machinery and municipal facilities. (3) The impact 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 i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C09K9/02C08J5/18C08L53/02C08K5/3432G01N21/64
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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