A kind of dithienylethylene compound with tetraphenylethylene unit and its preparation method and application

A technology of dithienylethylene and tetraphenylethylene, applied in chemical instruments and methods, organic chemistry, instruments, etc., to achieve the effect of cheap and easy-to-obtain raw materials, rich functions, and broad application prospects

Inactive Publication Date: 2020-07-17
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Dithiopheneethylene is an excellent photochromic molecular switch. The gated non-destructive reading of information is an important prerequisite for its functionalization. However, the research on dithiopheneethylene-based gated molecular switches is often concentrated in the solution state. , the gated molecular switch in the solid state has not been reported

Method used

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  • A kind of dithienylethylene compound with tetraphenylethylene unit and its preparation method and application
  • A kind of dithienylethylene compound with tetraphenylethylene unit and its preparation method and application
  • A kind of dithienylethylene compound with tetraphenylethylene unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthesis of compound shown in formula (I), synthetic route is as follows:

[0048]

[0049] THF in the reaction formula is tetrahydrofuran.

[0050] Concrete synthetic steps are as follows:

[0051] Under the protection of nitrogen, tetraphenylethyleneaniline (0.5 g, 1.29 mmol), 30 mL of anhydrous tetrahydrofuran and 1 mL of triethylamine were sequentially added into a 100 mL reaction flask. Under the condition of ice-water bath, 1,2-bis(5-methylthiophene-2-yl chloride)cyclopentene (0.25g, 0.65mmol) in tetrahydrofuran was slowly added dropwise into the reaction system, and reacted overnight at 60°C. After the reaction, cool to room temperature, extract three times with dichloromethane, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, remove the solvent under reduced pressure, and separate the light yellow solid through column chromatography, which is the formula ( The compound shown in I) has a yield of 43%.

[0052] ...

Embodiment 2

[0054] Reversible mechanochromic properties of compounds

[0055] The compound of Example 1 was processed and tested in the following different ways.

[0056] 1) Take the solid of the compound prepared in Example 1, and use 330nm as excitation light to test its fluorescence emission spectrum.

[0057] 2) Put the solid of the compound prepared in Example 1 into a mortar and grind it thoroughly, and use 330nm as excitation light to test its fluorescence emission spectrum.

[0058] 3) The solid of the compound prepared in Example 1 was thoroughly ground in a mortar, and the ground solid powder was heated at 150° C. for 3 min and cooled to room temperature, and its fluorescence emission spectrum was measured with 330 nm as excitation light.

[0059] 4) Put the solid of the compound prepared in Example 1 into a mortar and grind it thoroughly, and then dissolve the ground solid powder with dichloromethane. After the solvent evaporates, use 330nm as the excitation light to test its ...

Embodiment 3

[0062] Photochromic Properties of Compound Solids

[0063] The compound of Example 1 was processed and tested in the following different ways.

[0064] 1) Get the solid of the compound prepared in Example 1, alternately irradiate with ultraviolet light and visible light of 254nm, test its ultraviolet-visible absorption spectrum, as figure 2 shown.

[0065] 2) The solid of the compound prepared in Example 1 is placed in a mortar and thoroughly ground, alternately irradiated with 254nm ultraviolet light and visible light, and tests its ultraviolet-visible absorption spectrum, such as image 3 shown.

[0066] 3) Put the solid of the compound prepared in Example 1 into a mortar and grind it thoroughly, heat the ground solid powder at 150°C for 3 minutes and cool it to room temperature, and alternately irradiate it with 254nm ultraviolet light and visible light to test its ultraviolet light. - Visible absorption spectra, such as Figure 4 shown.

[0067] Depend on figure 2 ...

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Abstract

The invention belongs to the technical field of photochromic materials, and relates to a dithiophene ethylene compound with a tetraphenyl ethylene unit as well as a preparation method and applicationthereof. A chemical structural formula of the dithiophene ethylene compound is as shown in a formula (I) which is shown in the description. The dithiophene ethylene compound is an intelligent chromatic material, and the solid photochromatic characteristics of the dithiophene ethylene compound can be dynamically controlled through external mechanical grinding and annealing. (The formula is shown inthe description.).

Description

technical field [0001] The invention belongs to the field of photochromic materials, and more specifically relates to a dithienylethylene compound with tetraphenylethylene units and a preparation method and application thereof. Background technique [0002] Photochromism refers to the obvious changes in the photochemical and photophysical properties of compounds before and after the photocyclization reaction. As photochromic materials, optical switch molecules can be widely used in molecular logic gates, data storage, multi-photonic devices, surface nano-devices, optoelectronic devices, electrochemical wires, liquid crystal materials and other fields. [0003] There are many kinds of organic photochromic materials, mainly including azobenzenes, fulgid anhydrides, spiropyrans, spirooxazoles, diarylethenes and related heterocyclic compounds. Among them, diarylethene compounds have attracted extensive attention of scientists due to their higher thermal stability, better fatigu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/38C09K9/02G02C7/10
CPCC07D333/38C09K9/02C09K2211/1007C09K2211/1092G02C7/102
Inventor 尹军韩勰潘颖乐刘盛华
Owner HUAZHONG NORMAL UNIV
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