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Unsymmetrical naphthalene-pyrrole hybrid diarylethene compound and its application

A diarylethene, asymmetric technology, applied in the direction of organic chemistry, organic chemical methods, chemical instruments and methods, etc., to achieve the effect of low cost, mature reaction conditions, and high sensitivity

Active Publication Date: 2022-05-06
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, using perfluorocyclopentene as the bridgehead unit of diarylethene compound, selecting pyrrole ring and naphthalene ring as side group units to construct asymmetric naphthalene-pyrrole hybrid perfluorocyclopentene has not yet seen any literature and patents to report

Method used

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  • Unsymmetrical naphthalene-pyrrole hybrid diarylethene compound and its application
  • Unsymmetrical naphthalene-pyrrole hybrid diarylethene compound and its application
  • Unsymmetrical naphthalene-pyrrole hybrid diarylethene compound and its application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Compound 1 {1-(2-methyl-1-naphthyl), 2[-1,5-dimethyl-2-cyano-pyrrol-4-yl]} preparation process of perfluorocyclopentene

[0028] In the molecular structure formula, when R is cyano (-CN), the photochromic compound 1O is formed, and its name is: {1-(2-methyl-1-naphthyl), 2[-1, The structural formula of 5-dimethyl-2-cyano-pyrrol-4-yl]} perfluorocyclopentene is as follows:

[0029]

[0030] The synthetic scheme of this novel perfluorocyclopentene diarylethene compound is shown in Scheme1

[0031] The synthetic scheme of compound 10 is shown in formula Scheme 1:

[0032]

[0033] Concrete synthetic steps are as follows:

[0034] 1. 4-bromo-1,5-dimethyl-2-cyanopyrrole (2)

[0035] Under ice-bath conditions, dissolve 1,5-dimethyl-2-cyanopyrrole (5.0-6.0 g, 40-50 mmol) in a single-necked flask filled with 100.0 mL of acetic acid, and use a constant pressure dropping funnel to Slowly add 20.0 mL of acetic acid containing 2.2 mL of liquid bromine dropwise, stir and rea...

Embodiment 2

[0044] Synthesis of Compound 2{1-(2-methyl-1-naphthyl,2-[1,5-dimethyl-2-formamido-pyrrol-4-yl]}perfluorocyclopentene (2O) process:

[0045] In the molecular structure formula, when R=-CONH 2 , which constitutes the compound {1-(2-methyl-1-naphthyl, 2-[1,5-dimethyl-2-formamido-pyrrol-4-yl]} perfluorocyclopentene, structural formula as follows:

[0046]

[0047] Compound {1-(2-methyl-1-naphthyl, 2-[1,5-dimethyl-2-formamido-pyrrol-4-yl]} The synthetic scheme of perfluorocyclopentene is shown in the formula Scheme 2 shows:

[0048]

[0049] Concrete synthetic steps are as follows:

[0050] At room temperature, dissolve compound 1O (0.44~0.65g, 1.0~1.5mmol) in DMSO solution, add 0.4molL -1 K 2 CO 3 solution and 2.0mL H 2 o 2 , after reacting for 12 hours, dilute with water and filter with suction to obtain white solid compound 2O (0.25-0.42 g, 0.55-0.92 mmol). Yield: 55.6-65.2%.

[0051] Product structure identification: 1 H-NMR (400MHz, CDCl 3 ):δ1.86(s,3H),2.29(...

Embodiment 3

[0053] Staining of HeLa cells:

[0054] At 37°C, 5% carbon dioxide and 95% air. HeLa cells were placed in a cell culture dish in 20 mL of 10% DMEM bovine serum and allowed to persist overnight before experiments. After the HeLa cells were washed with phosphate-buffered saline (PBS), Compound 1 and Compound 2 (20 μM) were incubated in the culture medium for 30 minutes, respectively. After washing the HeLa cells with PBS three times, the cells were imaged with an Olympus FV1000 laser confocal laser scanning microscope, excited with a 405nm laser, and the fluorescence signals at 400-500nm in the blue channel were collected.

[0055] The main uses of the naphthalene ring-pyrrole mixed-type photochromic perfluorocyclopentene compound molecule of the present invention are: using its good photochromic, thermal stability and other properties, it can be used as an optical storage medium or an optical control switch Component; Utilizing the fluorescent properties of compound molecules...

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Abstract

The invention belongs to the field of photochromic materials, and relates to a synthesis method and application of an asymmetric naphthalene-pyrrole perfluorocyclopentene compound. The prepared two compounds have remarkable aggregation-induced luminescence characteristics. The invention provides a preparation method for the compound described in the above scheme. The preparation method provided by the invention has simple steps, low cost, milder preparation conditions, and is more suitable for industrial production. It has a large application prospect and is aimed at cell fluorescence imaging and organic photoluminescence. The cold light material has better application effect.

Description

technical field [0001] The invention belongs to the field of photochromic materials, and relates to a synthesis method and an application of an asymmetric naphthalene-pyrrole perfluorocyclopentene compound. Background technique [0002] With the rapid development of science and technology, people's performance requirements for storage materials are gradually increasing. Compared with traditional storage materials, organic photochromic storage materials have great advantages in storage density and storage speed. The currently widely reported organic photochromic compounds mainly include Schiff base, fulgid anhydride, spiropyran, azobenzene, diarylethene, etc. These compounds can undergo reversible discoloration under the irradiation of different wavelengths of light. This feature can cause significant changes in the physical and chemical properties of the compound, so that photochromic compounds have broad applications in many fields such as light-controlled molecular switch...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34C09K9/02C09K11/06G01N21/64
CPCC07D207/34C09K9/02C09K11/06G01N21/6428C09K2211/1029C09K2211/1007C09K2211/1011C07B2200/13G01N2021/6439
Inventor 蒲守智王仁杰张洁刘刚
Owner JIANGXI SCI & TECH NORMAL UNIV
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