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Molecular switch with multiple stimulation responses and synthesis method thereof

A technology of multiple stimuli responses and synthesis methods, applied in chemical instruments and methods, analyzing materials through chemical reactions, and analyzing materials through observing the influence of chemical indicators, can solve the problems of poor reversibility and poor reaction yields. High-level problems, to achieve the effect of rapid reaction, simple synthesis route, and easy purification

Pending Publication Date: 2022-06-03
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these DASAs have been unable to meet the needs of social development due to the low reaction yield (only 75%) and only a single light stimulus, which has poor reversibility ([1] Design and Synthesis of Donor-Acceptor Stenhouse Adducts: A Visible Light Photoswitch Derived from Furfural.Sameh Helmy,et al.Journal of the Organic Chemistry,2014,79,11316-11329.[2]Tunable Visible and Near Infrared Photoswitches.James R.Hemmer,etal.Journal of the American Chemical Society, 2016,138,13960-13966)

Method used

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  • Molecular switch with multiple stimulation responses and synthesis method thereof
  • Molecular switch with multiple stimulation responses and synthesis method thereof
  • Molecular switch with multiple stimulation responses and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Compound I of the present invention is 5-(furan-2-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, and its molecular structure is as follows Show:

[0036]

[0037] Prepared by the following steps:

[0038] In the double-necked flask, according to the molar ratio of 2-furancarboxaldehyde: cycloisopropylmalonate=1.1:1, firstly add cycloisopropylidene malonate into the flask, then add deionized water as a solvent, 2-furancarboxaldehyde was slowly added dropwise with stirring, and the reaction was carried out at 25° C. for 2 h. After the reaction, add CH 2 Cl 2 Extraction of crude product, CH 2 Cl 2 The aqueous phase was extracted (25ml*3), and the organic phase was collected. Saturated NaCl solution and saturated NaHSO were added successively. 4 , saturated NaHCO 3 solution, for CH 2 Cl 2 The phase was washed, and then a small amount of water in the organic phase was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and ...

Embodiment 2

[0044] Reversible photoresponse test of compound II:

[0045] Under visible light irradiation (>535nm), in toluene solution, the photoisomerization of compound II (in toluene, c=1.0×10 - 5 mol / L). Its performance characteristics see Figure 7-8 .

[0046] Figure 7 a is the absorption spectrum of compound II in different concentrations of toluene as a function of concentration, and the maximum absorbance is at 544 nm. b is a linear relationship between the absorbance at 544nm and the concentration of compound II. This shows that the toluene solution of compound II has a good linear relationship and the maximum absorption wavelength does not change with the concentration.

[0047] from Figure 8 It can be seen that the absorbance of compound II decreased to 0.1 under the illumination of >535nm light for 1min, and then placed in the dark, the absorbance would rise slowly, and the absorbance reached the maximum after being placed for 20min. Then repeat the light until the a...

Embodiment 3

[0049] Reversible acid-base response test of compound II:

[0050] Figure 9a It is the color change diagram of the acid-base response of compound II in DMSO solution, 1 is the initial state of the sample; 2 is the state after adding equimolar amount of base; 3 is the state after adding equimolar amount of acid. b: Compound Ⅱ in DMSO-d 6 The NMR test of adding acid and adding base is carried out in the figure, and the characteristic NMR spectrum of the conjugated olefin region of compound II is intercepted in the figure, 1 is the initial state of the sample; 2 is the state after adding an equimolar amount of base; 3 is an equimolar amount added state after acid. This shows that compound Ⅱ can obtain an intermediate isomer by adding alkali in DMSO, and then can be restored to the original state by adding acid, showing a good switching potential, and can carry out many cycles, and has excellent anti-fatigue performance.

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Abstract

The invention discloses a molecular switch with multiple stimulation responses and a synthesis method thereof. The molecular switch is 5-((2Z, 4E)-2-hydroxy-5-((2-ethoxyl) (methyl) amino)-2, 4-diene-1-subunit)-2, 2-dimethyl-1, 3-dioxane-4, 6-diketone, the structural formula of the molecular switch is 5-(furan-2-yl methylene)-2, 2-dimethyl-1, 3-dioxane-4, 6-diketone I synthesized by mixing 2-furan formaldehyde and malonic acid cycloisopropylidene ester and reacting, and the molecular switch is 5-((2Z, 4E)-2-hydroxy-5-((2-ethoxyl) (methyl) amino)-2, 4-diene-1-subunit)-2, 2-dimethyl-1, 3-dioxane-4, 6-diketone. And then reacting with N-methyl-2-hydroxyethylamine to generate the molecular switch. The adopted raw materials are clean and environment-friendly, the synthesis method is simple, and the obtained target compound has the advantages of high yield and high purity. The molecular switch has reversible response to visible light and acid-base, has obvious color response to low temperature, and can be used as a photochromic material, a drug release carrier, a temperature sensor and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a molecular switch with multiple stimulus responses and a synthesis method thereof. Background technique [0002] Organic stimuli-responsive materials can undergo a series of reversible changes in certain physical and chemical properties, specifically in spectral absorption, solubility, viscosity, polarity, electrochemical properties, electrical conductivity, refractive index, etc., which are important for chemical biosensing. And the development of encryption for information storage is of great significance. As a stimulus, light has many advantageous advantages, such as energy saving and high efficiency, no physical contact, high spatial and temporal resolution, and easy adjustment (Photochromism intonanosystems: towards lighting up the future nanoworld. Wang Ling, LiQuan. Chemical Society Reviews, 2018, 47, 1044-1097.). [0003] Light-driven optical switch molecules h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C09K9/02G01N21/31G01N21/78G01K11/16
CPCC07D319/06C09K9/02G01N21/31G01N21/78G01K11/16C09K2211/1088
Inventor 暴欣蒋仕青
Owner NANJING UNIV OF SCI & TECH
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