Acid-base and photochromic molecular switch and synthesis method thereof

A photochromic and molecular switching technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of low yield, expensive raw materials, poor selectivity, etc. Effect

Active Publication Date: 2021-02-26
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the disadvantages of expensive raw materials, low yield, poor selectivity, need to use ultraviolet light to undergo isomerization, incomplete isomerization, and small molecular conformation transformation in the prior art, the purpose of the present invention is to provide an acid-base and light Chromogenic molecular switch and synthesis method

Method used

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  • Acid-base and photochromic molecular switch and synthesis method thereof
  • Acid-base and photochromic molecular switch and synthesis method thereof
  • Acid-base and photochromic molecular switch and synthesis method thereof

Examples

Experimental program
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Effect test

preparation example 1

[0052] Compound I of the present invention has a molecular structure as follows:

[0053]

[0054] The preparation method and synthetic route of the compound of this example 1 are as follows:

[0055]

[0056] Add 1,3-dimethylbarbituric acid and furfural to H 2 O middle. The heterogeneous mixture was stirred at room temperature for 2 hours, during which time a yellow precipitate formed. After the reaction (TLC) detection, hexane:ethyl acetate=3:1. The mixture was vacuum filtered to collect the precipitated solid and washed twice with cold water. The collected solid was dissolved in dichloromethane and washed with saturated NaHSO 3 、H 2 O, saturated NaHCO 3 and washed with brine. MgSO for organic layer 4 After drying and filtering, the solvent was removed by a rotary evaporator to obtain a bright yellow powder, whose NMR spectrum was shown in figure 1 .

example 2

[0058] Compound II, its molecular structure is as follows:

[0059]

[0060] The preparation method and synthetic route of the compound of this example 2 are as follows:

[0061]

[0062] In the two-necked flask, according to the molar ratio of compound I:N,N,N-trimethylethylenediamine=1:1, add THF sequentially. The mixture was stirred at 23°C for 10 minutes, then cooled at 0°C for 20 minutes. After the reaction was complete, the mixture was filtered to collect solids. The solid was washed with cold ether and dried in vacuo to obtain a green solid whose structural characterization is shown in Figure 2-4 .

example 3

[0064] Compound III, its molecular structure is as follows:

[0065]

[0066] Compound II was recrystallized in acetonitrile at 50°C and left for 2 days to obtain Compound III. For its structural characterization, see Figure 5-7 , whose IR see Figure 13 , whose XRD see Figure 14 .

[0067]

[0068] The crystal data obtained after recrystallization of compound II are shown in Table 1-2 below.

[0069] Table 1 Crystal parameters

[0070]

[0071]

[0072] Table 2 Bond length between atoms

[0073]

[0074]

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Abstract

The invention discloses an acid-base and photochromic molecular switch and a synthesis method thereof, which comprises the following steps: reacting 1, 3-dimethyl ethylenediamine with furfural to synthesize a compound I, adding N, N, N-trimethylethylenediamine to generate a target compound II, recrystallizing in an acetonitrile solution to synthesize an isomer III, adding base into the isomer IIIsolution, converting into an isomer IV, adding acid into the solution of the compound IV to be converted into an isomer V, and adding alkali into the solution of the isomer V to be completely converted into an isomer IV. The organic photochromic compound with high yield and high content is obtained by using an organic solvent with lower toxicity and carrying out condensation reaction under certainconditions, and a catalyst is not needed, so that the production cost is effectively reduced, a synthesized molecular switch can be widely applied to the fields of intelligent windows, rewritable carbon paper, information storage, sensors, high-density optical memories, solar energy conversion, natural photosynthetic reaction process simulation, display, protection, decoration, photography, photomechanics, photosensitivity and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and mainly relates to a molecular switch and a synthesis method thereof. Background technique [0002] Smart systems built from molecular switches respond to external triggers (such as light, electricity, heat, sound, and pH) by changing molecular properties (color, polarity, shape, conductivity, reactivity, etc.) as it can through structural changes that modulate these physical responses. Various photochromic molecules, including azobenzenes, stilbenes, spiropyrans, and arylethenes, have been extensively studied and used to construct photoresponsive systems and materials. Each optical switch has its advantages and disadvantages; for example, azobenzene compounds are simple in structure and easy to synthesize; unfortunately, the yield of trans-cis conversion is usually far from quantitative. Diarylethenes are not suitable for the design of mechanically switchable structures because th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/62C07D403/04C09K9/02
CPCC07D239/62C07D403/04C09K9/02C09K2211/1044
Inventor 暴欣蔡佑德陈秀琴
Owner NANJING UNIV OF SCI & TECH
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