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Bis-pyrene type compound with piezochromic property and preparation method and application thereof

A piezochromic and compound technology, applied in chemical instruments and methods, condensation preparation of carbonyl compounds, organic chemistry, etc., can solve the problem of scarcity of piezofluorochromic materials

Active Publication Date: 2014-07-16
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of piezofluorochromic materials is still very rare.

Method used

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  • Bis-pyrene type compound with piezochromic property and preparation method and application thereof
  • Bis-pyrene type compound with piezochromic property and preparation method and application thereof
  • Bis-pyrene type compound with piezochromic property and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Take the R structure as C 12 h 25 as an example

[0078] 1. Synthetic method of compound:

[0079] Etherification reaction of compound 1: add 10mmol compound 1 (2.38g), acetone (100mL), 10mmol potassium carbonate (1.37g), compound 10mmol C 12 h 25 Br (2.49g), heated to reflux for 12 hours, concentrated to obtain a crude product, separated by column chromatography, eluted with a mixed solvent of dichloromethane / petroleum ether (volume ratio 2:1), and rotatively evaporated the solvent to obtain a white solid compound 2 (3.07 g, yield: 75.6%).

[0080] Hydrolysis reaction of compound 2: add 30mL ethanol, 60mL water, 5mmol compound 2 (2.03g) and 10mmol potassium hydroxide (0.56g) into the there-necked flask, heat and reflux for 5 hours, add 1M hydrochloric acid dropwise to pH=3 after cooling, Filtration gave white solid compound 3 (1.65 g, yield: 94.3%).

[0081] The acid chlorination reaction of compound 3: in the room equipped with thermometer, dropping funnel, refl...

Embodiment 2

[0088] Take the R structure as C 3 h 7 as an example

[0089] Etherification reaction of compound 1: add 10mmol compound 1 (2.38g), acetone (100mL), 10mmol potassium carbonate (1.37g), compound 10mmol C 12 h 25 Br (1.23g), heated to reflux for 12 hours, concentrated to obtain a crude product, separated by column chromatography, eluted with a mixed solvent of dichloromethane / petroleum ether (volume ratio 3:1), and rotatively evaporated the solvent to obtain a white solid compound 2 (2.04 g, yield: 73.0%).

[0090] Hydrolysis of Compound 2: Add 30mL of ethanol, 60mL of water, 5mmol of Compound 2 (1.42g) and 10mmol of potassium hydroxide (0.56g) into a three-neck flask, heat to reflux for 5 hours, add dropwise 1M hydrochloric acid to pH=3 after cooling, Filtration gave white solid compound 3 (1.08 g, yield: 96.4%).

[0091] The acid chlorination reaction of compound 3: in the room equipped with thermometer, dropping funnel, reflux condenser (with HCl and SO 2 Add 50mmol of ...

Embodiment 3

[0098] With R structure as (CH 2 CH 2 O) 2 CH 3 as an example

[0099] The etherification reaction of compound 1: add 10mmol compound 1 (2.38g), acetone (100mL), 10mmol potassium carbonate (1.37g), compound 10mmol Br(CH 2 CH 2 O) 2 CH 3 (1.81g), after heating to reflux for 12 hours, concentrated to obtain the crude product, separated by column chromatography, eluted with a mixed solvent of dichloromethane / petroleum ether (volume ratio 3:1), and rotary evaporated the solvent to obtain white solid compound 2 (2.13 g, yield: 71.0%).

[0100] Hydrolysis reaction of compound 2: add 30mL ethanol, 60mL water, 5mmol compound 2 (1.58g) and 10mmol potassium hydroxide (0.56g) into the there-necked flask, heat and reflux for 5 hours, add 1M hydrochloric acid dropwise to pH=3 after cooling, Filtration gave white solid compound 3 (1.21 g, yield: 94.4%).

[0101] The acid chlorination reaction of compound 3: in the room equipped with thermometer, dropping funnel, reflux condenser (w...

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Abstract

The invention discloses a bis-pyrene type compound with piezochromic property and a preparation method and application thereof. The compound has the structure as shown in general formula (I), and the preparation is completed by four-step conventional reactions, namely etherification reaction, hydrolysis reaction, chloroformylation reaction and Friedel-Crafts acylation reaction. The bis-pyrene type compound disclosed by the invention can be used for preparing a thin film in a spin-coating way, and the thin film has piezochromic luminescent property with high repeatability, high contrast and high sensitivity and can be used for information storage.

Description

technical field [0001] The invention relates to a bispyrene compound with piezochromic properties, a preparation method and an application thereof. Background technique [0002] Small organic molecular piezofluorescent materials have a wide range of uses. They can not only be used in display screens and recorders as sensors, information displays and memories, but also in a variety of emerging fields, such as security Stationery, light sticks, etc. With the development of science and the progress of society, people's demand for small organic molecule piezofluorochromic materials with special uses has further increased, so it is of great importance to develop new functional materials with special functions significance. [0003] As a fluorescent sensor, organic small molecule fluorescent materials have the advantages of high sensitivity, good selectivity, short response time, and direct observation. Therefore, in recent years, research on fluorescent sensors for the detecti...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/46C09K9/02D21H21/48D21H27/26
Inventor 王浩王磊李微杨培培
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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