3-aryl-2-cyanoacrylamide derivative as well as preparation method and application thereof

A technology of cyanoacrylamide and derivatives, applied in the application of pressure-sensitive materials, organic small molecules and its preparation field, can solve the problems of lack of in-depth understanding of the formation mechanism of discoloration phenomenon, rare types of materials, limited quantities, etc., and achieve good results Reversible stimulus-responsive mechanochromic properties, low equipment requirements, and convenient post-processing effects

Active Publication Date: 2014-08-06
山西鸿生化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, the kinds of materials that can achieve discoloration by adjusting the stacking mode are rare and limited, and the fundamental reason is that there is a lack of in-depth understanding of the formation mechanism of the discoloration phenomenon.

Method used

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  • 3-aryl-2-cyanoacrylamide derivative as well as preparation method and application thereof
  • 3-aryl-2-cyanoacrylamide derivative as well as preparation method and application thereof
  • 3-aryl-2-cyanoacrylamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Preparation of 2-cyano-3-(4-methoxyphenyl)-2-acrylamide

[0038] Add 4-methoxybenzaldehyde (1.36g, 10mmol), cyanoacetamide (0.84g, 10mmol), L-proline (0.058g, 0.5mmol) into 15ml of absolute ethanol in sequence, stir and heat to reflux After the reaction of 4-methoxybenzaldehyde is complete (TLC tracking reaction), cool to room temperature, a white solid precipitates, vacuum filter, wash the filter cake with a mixed solution of ethanol and water (volume ratio 1:1), and dry 1.82 g of white solid product was obtained with a yield of 90.1%.

[0039] 1 H NMR (500 MHz, DMSO): δ 8.11 (s, 1H), 7.97 (d, J = 8.8 Hz, 2H), 7.79 (s, 1H), 7.73 – 7.59 (m, 1H), 7.14 (t, J = 5.8 Hz, 2H), 3.86 (s, 3H). 13 C NMR (126 MHz, DMSO): δ 163.1, 162.6, 150.1, 132.4, 124.4, 117.0, 114.8, 102.9, 55.6, 54.9.

[0040] In the above examples, 4-methoxybenzaldehyde is replaced by other methoxy-substituted benzaldehydes, all of which can achieve the same technical effect.

Embodiment 2

[0042] With the operation of Example 1, the solvent is anhydrous methanol, and the 4-methoxybenzaldehyde: cyanoacetamide: the amount of substance ratio of L-proline is changed from 1:1:0.05 to 1:1:0.10, 1.85 g of white pure product was obtained with a yield of 91.6%.

Embodiment 3

[0044]With the operation of Example 1, the amount ratio of 4-methoxybenzaldehyde: cyanoacetamide: L-proline is changed from 1:1:0.05 to 1:1:0.15 to obtain 1.87g of white pure product , and the yield was 92.6%.

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Abstract

The invention discloses a 3-aryl-2-cyanoacrylamide derivative, a preparation method and application thereof, and belongs to the technical field of fluorescent material synthesis. The preparation method comprises the following steps: in an alcohols solvent, taking methoxyl substituted benzaldehyde as shown in formula (II) and cyanoacetamide as shown in formula (III) as raw materials, under catalysis of L-proline, performing a Knoevenagel condensation reaction to prepare the 3-aryl-2-cyanoacrylamide derivative. The preparation method has the advantages of mild reaction conditions, simple operation, convenient aftertreatment, low equipment requirements and high yield of the obtained product; the fluorescence color of the product after grinding can be changed, the color contrast ratio before and after change is high; in the meantime, the ground sample can be heated or suffocated with vapors of multiple organic solvents to recover the initial color, so that the 3-aryl-2-cyanoacrylamide derivative is high in reversible stimuli-responsive force-induced color changing performance, and can be applied to the sensor field, the anti-counterfeit field, the storage field, the display field, and the like.

Description

[0001] and application technology [0002] The invention belongs to the technical field of fluorescent material synthesis, and specifically relates to a small organic molecule with reversible mechanochromic properties, a preparation method thereof, and an application in pressure-sensitive materials. The color change of the reversible piezochromic organic small molecule of the invention has high contrast, rapid reversal, simple preparation and convenient application, and is suitable for sensors, anti-counterfeiting, storage and display. Background technique [0003] Compared with inorganic solid materials, organic solid materials have the advantages of strong modifiability, variety, and high molar extinction coefficient, so they are widely used in organic light-emitting diodes (OLEDs), organic fluorescent sensors and other fields. [0004] Currently, there are two methods for adjusting the color of organic light-emitting materials. One is to change the structure of the molecul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/41C09K9/02
Inventor 宋庆宝张诚王永胜沈田华欧阳密
Owner 山西鸿生化工股份有限公司
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