Triphenylamine derivatives as well as preparation method and application thereof

A derivative, triphenylamine technology, applied in the field of triphenylamine derivatives and its preparation and application, can solve problems such as limiting the application of materials

Active Publication Date: 2013-05-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the reversible piezochromic phenomenon reported so far mainly focuses on small molecules, oligomers, liquid crystals and doped polymers, which will greatly limit the application of such materials.

Method used

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  • Triphenylamine derivatives as well as preparation method and application thereof
  • Triphenylamine derivatives as well as preparation method and application thereof
  • Triphenylamine derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of intermediate

[0037]Dissolve 3.47g (12mmol) of triphenylamine 4-boronate, 1.96g (10mmol) of p-bromonitrile benzyl, 0.11g (0.1mmol) of tetrakis(triphenylphosphine)palladium in a mixture of 50mL of toluene / 30mL of tetrahydrofuran, and add carbonic acid Aqueous sodium solution (2.0M, 3mL). Under the protection of nitrogen, raise the temperature to 90°C for 36 hours. After the reaction, cool the reaction solution to room temperature (25°C) and extract with chloroform. Take the lower layer of the extract (that is, the chloroform layer) and wash it with saturated brine. Dry with anhydrous magnesium sulfate, filter, and concentrate the filtrate to dryness under reduced pressure. The concentrate is subjected to silica gel column chromatography with a mixture of chloroform and petroleum ether at a volume ratio of 1:150, followed by TLC detection. The eluate of the product (III) was distilled to remove the solvent to obtain 2.76 g of a yellow po...

Embodiment 2

[0038] The preparation of embodiment 2 intermediate

[0039] Dissolve 3.47g (10mmol) of triphenylamine 4-boronate, 1.96g (10mmol) of benzyl p-bromonitrile, and 0.55g (0.5mmol) of tetrakis(triphenylphosphine)palladium in a mixture of 50mL toluene / 30mL absolute ethanol, Aqueous potassium carbonate solution (2.0 M, 5 mL) was added. Under the protection of argon, heat up to 90°C and react for 16h. After the reaction, cool the reaction solution to room temperature (25°C) and extract with chloroform. Take the extract from the lower layer, wash it with saturated saline, and dry it with anhydrous magnesium sulfate. , filtered, and the filtrate was concentrated to dryness under reduced pressure, and the concentrate was subjected to silica gel column chromatography using a mixture of chloroform and petroleum ether at a volume ratio of 1:150 as the eluent, followed by TLC detection, and the eluent containing the target product (III) was collected. The liquid was removed, and the solvent...

Embodiment 3

[0040] Preparation of triphenylamine derivatives shown in embodiment 3 formula (I)

[0041] Get 1.80g (5 mmol) of intermediate (III) prepared in Example 1, 2.07g (6mmol) of p-hexadecyloxybenzaldehyde and 0.03g (0.5mmol) of sodium methoxide and dissolve it in 30ml of chromatographically pure ethanol. Stir and react at (25°C) for 3 hours, a large amount of solid particles terminated the reaction, then put the reaction solution in a -20°C refrigerator overnight and then filter, the filter cake was rinsed with absolute ethanol three times and then dried to obtain a yellow-green powder product (ie (I) the triphenylamine derivative) 3.1g, the yield is 90%. The structural confirmation of the substance is characterized as follows: 1 H NMR (500 MHz, CDCl 3 ) δ(ppm) 7.89 (d, J=8.5 Hz, 2H), 7.70 (d, J=8.5 Hz, 2H), 7.63 (d, J=9.0 Hz, 2H), 7.50 (d, J=7.0 Hz, 2H), 7.49 (s, 1H), 7.28 (t, J=8.5 Hz, 4H), 7.14 (d, J=8.0 Hz, 6H), 7.05 (t, J=7.5 Hz, 2H), 6.97 (d, J=8.5 Hz, 2H), 4.02 (t, J=6.5...

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Abstract

The invention discloses triphenylamine derivatives represented by a formula (I) as well as a preparation method and an application thereof in piezochromic organogel. The preparation method comprises the following steps of: mixing an intermediate, para-hexadecyloxy benzaldehyde and sodium methoxide, dissolving with absolute ethyl alcohol, stirring and reacting for 3 hours at room temperature, and separating the reaction liquid after the reaction is complete so as to obtain the triphenylamine derivatives represented by formula (I). The piezochromic organogel is a micromolecule organogel material with multiple simulation responsiveness. The piezochromic organogel is simple in synthesis method, convenient in preparation, strong in simulation responsiveness, and can be applied to fields such as a sensor, anti-fake, store and display.

Description

(1) Technical field [0001] The invention relates to a triphenylamine derivative, its preparation method and its application in the preparation of piezochromic organic gel. (2) Background technology [0002] The phenomenon that the fluorescence color changes when the material is subjected to mechanical force is called piezochromism, and substances with piezochromism have at least two stable or metastable accumulation modes affected by pressure. After being stimulated by a force, the internal force of the molecule changes, resulting in a change in the molecular packing method, which makes the material change from one ordered structure to another ordered or partially ordered or disordered structure, and the photophysical properties of the material change with time. change. Then, after being treated with heating and solvents, the accumulation mode of the molecules will return to the original, realizing the reversibility of the fluorescent color change. At present, the research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/43C07C253/30C09K11/06C09K9/02G01L1/24G01K11/16
Inventor 张诚孙璟玮张玉建欧阳密余承涛
Owner ZHEJIANG UNIV OF TECH
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