Mechanochromic diethyl terephthalate compound, as well as preparation method and application thereof

A technology of diethyl terephthalate and diethyl phthalate, which is applied in the field of diethyl terephthalate compounds and their preparation, can solve problems such as the expansion of functional materials, achieve good optical stability, and prepare Simple method, high reproducibility effect

Active Publication Date: 2018-12-07
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the variety of such functio

Method used

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  • Mechanochromic diethyl terephthalate compound, as well as preparation method and application thereof
  • Mechanochromic diethyl terephthalate compound, as well as preparation method and application thereof
  • Mechanochromic diethyl terephthalate compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Take 10g of 2,5-dibromoterephthalic acid in a 100mL round-bottomed flask, add 20mL of thionyl chloride under stirring, heat to reflux for 10 hours, and distill off excess thionyl chloride under normal pressure to obtain the corresponding acid chloride. Slowly add 10 mL of absolute ethanol dropwise under cooling at 0°C, after the dropwise addition is complete, stir at room temperature for 6 hours, evaporate the solvent to dryness to obtain diethyl 2,5-dibromoterephthalate. mp 126-127°C.

[0039] 1 H NMR (CDCl 3 , 300MHz, ppm) 8.22 (s, 2H), 4.40 (q, 4H, J = 7.1Hz), 1.40 (t, 6H, J = 7.20Hz).

Embodiment 2

[0041] Get 10-ethyl-3-vinyl phenothiazine (0.50g), 2,5-dibromodiethyl terephthalate (0.40g), potassium carbonate (0.80g), tetrabutylammonium bromide ( 1.20 g) and 10 mg of palladium chloride were placed in a 50 mL round bottom flask, 20 mL of dry DMF was added, nitrogen gas flowed for 10 minutes, and the reaction was carried out under nitrogen protection at 120° C. for 12 hours. Cool, pour into 100mL water, filter with suction and dry. Purified by column chromatography (dichloromethane / petroleum ether (2:1) as eluent) to obtain a yellow solid: 2,5-bis((10-ethyl-10-hydrogen-phenothiazin-2-yl) Vinyl) diethyl terephthalate. Yield 87%.

[0042] 1 H NMR (400MHz, CDCl 3 ,ppm)8.17(d,J=1.9Hz,2H),7.75(d,J=16.2Hz,2H),7.29(d,J=6.9Hz,4H),7.17–7.08(m,4H),6.95( d,J=16.1Hz,2H),6.92–6.77(m,6H),4.44(qd,J=7.1,1.6Hz,4H),3.91(s,4H),1.50–1.35(m,12H). 13 C NMR (101MHz, CDCl 3,ppm)167.07,144.64,144.43,136.91,131.77,131.55,130.62,128.73,127.36,127.29,126.28,125.35,124.56,124.30,123.82,122.48,1...

Embodiment 3

[0044] Get 10-butyl-3-vinylphenothiazine (0.50g), 2,5-dibromodiethyl terephthalate (0.33g), potassium carbonate (0.75g), tetrabutylammonium bromide ( 1.10 g) and 10 mg of palladium chloride were placed in a 50 mL round-bottomed flask, 20 mL of dry DMF was added, nitrogen gas flowed for 10 minutes, and the reaction was carried out under nitrogen protection at 120° C. for 12 hours. Cool, pour into 100mL water, filter with suction and dry. Purified by column chromatography (dichloromethane / petroleum ether (2:1) as eluent) to obtain a yellow solid: 2,5-bis((10-butyl-10-hydrogen-phenothiazin-2-yl) Vinyl) diethyl terephthalate. Yield 89%.

[0045] 1 H NMR (400MHz, CDCl 3 ,ppm)8.18(s,2H),7.76(d,J=15.9Hz,2H),7.32(d,J=7.3Hz,4H),7.19–7.10(m,4H),6.97(d,J=16.1 Hz,2H),6.91–6.77(m,6H),4.44(q,J=7.2,4H),3.91(s,4H),1.86–1.74(m,4H),1.52–1.40(m,10H), 0.95(t,J=7.4Hz,6H). 13 C NMR (101MHz, CDCl 3 ,ppm)167.08,144.65,144.44,136.91,131.78,131.56,130.62,128.72,127.37,127.31,126.30,125.35,124.5...

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Abstract

The invention provides a mechanochromic diethyl terephthalate compound, as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein n is 2, 4, 6, 8, 12 and 16, can be applied to mechanochromic materials, information storage and landmark anti-counterfeiting and preparation of mechanochromic films. The preparation method is simple, and the film prepared by the method has excellent mechanochromic property, color under natural light and fluorescent color can be changed under mechanical force, and the film can be quickly restored to the original state under the atmosphere of an organic solvent or under a heating condition, so that the process has recyclability, which indicates that the compound can be recycled. The mechanochromic diethyl terephthalate compound has excellent optical stability, high repeatability and high contrast ratio, and has a wide application prospect in information storage and anti-counterfeitingaspects.

Description

technical field [0001] The invention belongs to the technical field of organic mechanochromic materials and anti-counterfeiting, and in particular relates to a mechanochromic diethyl terephthalate compound, a preparation method and an application thereof. Background technique [0002] In recent years, functional materials that respond to mechanical stimuli have received extensive attention. Under the stimulation of mechanical force, the conductivity, permittivity, mobility, luminous intensity or color of these materials change. Taking advantage of these properties, these functional materials can be utilized in electronic skins, pressure sensors, and damage detection. Among them, the mechanochromic light-emitting organic materials whose luminous color, luminous intensity and luminous lifetime change under mechanical stimulation are developing rapidly. Such materials have very important application values ​​in the fields of stress sensing, displacement or deformation detecti...

Claims

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Application Information

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IPC IPC(8): C07D279/18C09K9/02
CPCC09K9/02C07D279/18C09K2211/1037C09K2211/1007
Inventor 薛鹏冲
Owner TIANJIN NORMAL UNIVERSITY
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