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Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound

A piezochromic and quaternary phosphonium salt technology, which is applied in the field of quaternary phosphonium salt compounds and their preparation, can solve problems such as lack, design and synthesis difficulties, and achieve sensitivity to external pressure stimuli, excellent photostability, and simple post-processing Effect

Inactive Publication Date: 2017-01-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been some reports on piezochromic materials, the design and synthesis of such molecules are difficult due to the lack of in-depth research on the structure-activity relationship of such molecules and the lack of design theory of piezochromic molecules.

Method used

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  • Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound
  • Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound
  • Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: Preparation of tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate

[0038] a, the synthesis of intermediate pyrene benzyl bromide

[0039]

[0040] Phosphorus tribromide (1.75 g) was dissolved in tetrahydrofuran (5 mL). Pyrene benzyl alcohol (1.00 g) was added in batches to the above solution, and the reaction was continued at room temperature for 30 minutes before stopping the reaction. The reaction solution was suction filtered and washed with ether to obtain the yellow target pyrenebenzyl bromide (1.22 g, 96%).

[0041] b. Synthesis of the target tributyl (3-pyrenebenzyl) phosphorus bromide

[0042]

[0043] Under nitrogen, pyrenebenzyl bromide (0.59 g), tributylphosphine (0.75 mL) and ethyl acetate (10 mL) were added to the reaction flask. After heating up to 80 ºC for 8 hours, the reaction was stopped. After suction filtration, the solid was washed with ethyl acetate to obtain the target compound tributyl(3-pyrenebenzyl)phosphorus bro...

Embodiment 2

[0047] Example 2: The piezochromic ability of the target tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate

[0048] The compound tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate exhibits blue fluorescence in the initial state, and it exhibits green fluorescence after gently grinding with a spatula. And the green fluorescence can quickly recover to the original blue fluorescence after being treated with heating and solvent atmosphere. figure 2 It clearly shows that before and after grinding, the solid fluorescence emission wavelength of the compound tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate is red-shifted from 400 nm to 486 nm, and the wavelength red shift can reach 86 nm, heating and solvent atmosphere After treatment, its solid fluorescence returned to its original blue fluorescence (emission wavelength is 400 nm). image 3 It shows that the fluorescence change between blue fluorescence and green fluorescence of this compound can be repeated m...

Embodiment 3

[0049] Example 3: Piezochromic information storage of target tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate

[0050] Weighing paper coated with the compound tributyl(3-pyrenebenzyl)phosphonium hexafluorophosphate was used as a carrier for information storage. from Figure 4 It can be seen that the untreated weighing paper exhibits blue fluorescence under UV light. After gently writing on the weighing paper with a spatula, the written part showed a green fluorescent letter pattern, while the unwritten part was still blue fluorescent. During the whole process, the weighing paper is white in sunlight, and no letter pattern can be seen. The target tributyl (3-pyrenebenzyl) phosphonium hexafluorophosphate salt exhibits very different information storage capabilities.

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Abstract

The invention discloses a quaternary phosphonium salts compound with a piezochromism property and a preparation method and application of the quaternary phosphonium salts compound, and belongs to the field of function materials. The structural formula of the quaternary phosphonium salts compound is as shown in a formula I. In the formula I, Ar is anthracene, phenanthrene, pyrene, fluoranthene and the like, R is alkyl or aryl, and negative ions X are bromide ions, hexafluorophosphate ions, tetrafluoroborate ion, trifluoromethanesulfonate ions, bis-trifluoromethylsulfoandimide ions and the like. The quaternary phosphonium salts compound has quite excellent fluorescence piezochromism ability and high repeatability. In addition, the small organic molecule fluorescence piezochromism material further has the advantages of excellent light stability, sensitive stimulation to pressure of the outside and the like, and has wide application prospect in the aspects of information recording and storage.

Description

technical field [0001] The invention belongs to the field of functional materials, and in particular relates to a class of quaternary phosphonium salt compounds with piezochromic properties and a preparation method and application thereof. [0002] technical background [0003] As a new class of smart materials, small organic molecular piezofluorochromic materials have shown broad development prospects in many fields such as sensors, data storage, and security systems. Although there have been some reports on piezochromic materials, the design and synthesis of such molecules are difficult due to the lack of in-depth research on the structure-activity relationship of such molecules and the lack of design theory of piezochromic molecules. Compared with other stimuli-responsive fluorescent materials, organic small molecule piezofluorochromic materials are still very rare. Therefore, it is of great significance to develop a new class of high-efficiency organic small molecule pie...

Claims

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Application Information

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IPC IPC(8): C07F9/54C09K9/02
CPCC07F9/5456C09K9/02C09K2211/1011
Inventor 李高参王云兵杨立徐杨洋
Owner SICHUAN UNIV
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