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Preparation method and application of spiropyrane solid photostimulation-response compound

A compound and spiropyran technology, which is applied in the field of preparation of fluorescent stimulus-responsive compounds, can solve the problems of low isomerization efficiency and difficulty in isomerization, and achieve the effect of photo-stimulation response

Inactive Publication Date: 2019-08-13
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Firstly, spiropyran optical switch molecules have been widely studied and applied, but common spiropyrans are rarely coupled with AIE molecules to promote isomerization and the efficiency is not high; secondly, due to the strong molecular Accumulation makes isomerization difficult, so the isomerization studies of spiropyran are mostly in solution state, less in solid state

Method used

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  • Preparation method and application of spiropyrane solid photostimulation-response compound
  • Preparation method and application of spiropyrane solid photostimulation-response compound
  • Preparation method and application of spiropyrane solid photostimulation-response compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A solid-state fluorescent stimulus-responsive compound containing spiropyran and tetraphenylethylene, the specific structural formula of which is as follows:

[0024]

[0025] The preparation method is as follows:

[0026] (1) Synthesis of 2,3,3-trimethyl-N-hydroxyethylindole (compound A)

[0027]

[0028] Take by weighing 2,3,3-trimethyl-3H-indole (2.61g, 16mmol) and 2-bromoethanol (2.46g, 20mmol) and join in the three-necked flask of 100ml, then add solvent acetonitrile (20ml), pack With a good reflux device, under the protection of nitrogen, heat and reflux for 24 hours (oil bath 80 degrees), spin dry the solvent, wash with n-hexane three times, and then dry under reduced pressure to obtain 3.45 g of a purple solid with a yield of 75%. 1 H NMR (400MHz, CDCl 3 ), chemical shift (ppm): 7.93(t,1H,Ar-H),7.84(d,1H,Ar-H),7.60(t,1H,Ar-H),7.58,(d,1H,Ar-H H),4.57(t,2H,-NCH 2 CH 2 -O-),3.85(m,2H,-NCH 2 CH 2 -O-), 3.35(s,1H,-OH), 1.37(s,3H,C(N)(O)CH 3 ),1.31(s,3H,...

Embodiment 2

[0042] A solid-state fluorescent stimulus-responsive compound containing spiropyran and tetraphenylethylene, the specific structural formula of which is as follows:

[0043]

[0044] The preparation method is as follows:

[0045] Compound A, Compound B, Compound C, and synthetic steps refer to Example 1;

[0046] (1) Synthesis of Compound D

[0047] Weigh compound C (3g, 8.49mmol) and 1,2-dibromoethane (2.39g, 12.74mmol) into a 100ml three-necked flask, then add potassium carbonate (3.51g, 25.47mmol) and acetone (80ml) , install the reflux device, and heat to reflux for 24 hours under the protection of nitrogen. The solvent was spin-dried, and the crude product was purified by column chromatography (silica gel) using petroleum ether and ethyl acetate (6:1) as the eluent to obtain 2.69 g of light yellow solid powder with a yield of 70%.

[0048] (2) Synthesis of target product 2

[0049] Weigh compound D (1.5g, 3.26mmol) and tetraphenylethylene (0.39g, 1.08mmol) and add ...

Embodiment 3

[0051] A solid-state fluorescent stimulus-responsive compound containing spiropyran and tetraphenylethylene, the specific structural formula of which is as follows:

[0052]

[0053] The preparation method is as follows:

[0054] For the synthesis steps of compound A, compound B, compound C and compound D, see Example 1;

[0055] (1) Synthesis of Compound D

[0056] Weigh compound C (2.51g, 7.11mmol) and 1,2-dibromohexane (2.61g, 10.66mmol) into a 100ml three-necked flask, then add potassium bicarbonate (2.33g, 23.31mmol) and acetone (80ml), equipped with a reflux device, under nitrogen protection, heated to reflux for 24 hours. The solvent was spin-dried, and the crude product was purified by column chromatography (silica gel) using petroleum ether and ethyl acetate (6:1) as the eluent to obtain 2.48 g of light yellow solid powder with a yield of 68%.

[0057] (2) Synthesis of target product 3

[0058] Weigh compound D (2.2g, 4.27mmol) and tetraphenylethylene (0.517g, ...

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Abstract

The invention provides a spiropyrane solid photostimulation-response compound. The molecular chemical formula of the compound is shown in a formula (I). The invention discloses a preparation method and application of the solid fluorescence stimulation-response compound containing spiropyrane and tetraphenyl ethylene. The spiropyrane is a common photostimulation-response molecule, reversible structural isomerization between the spiropyrane as a colorless closed ring body and merocyanine as a colored open ring body can be generated, and due to high molecule accumulation of the spiropyrane in a solid state, the above-mentioned isomerization cannot easily occur; the typical aggregation-induced emission phenomenon occurs on the tetraphenyl ethylene, and the tetraphenyl ethylene is large in volume and provides the free volume for the spiropyrane, so that the isomerization of the spiropyrane in the solid state is facilitated; spacers are introduced between the tetraphenyl ethylene and the spiropyrane, which is beneficial for improvement of the luminous efficiency of the spiropyrane. In this way, the solid photochromic fluorescent molecular switch material is provided and has wide application prospects in the fields of photoswitch molecular devices, anti-fake application, optical information storage and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method and application of a fluorescent stimulus-responsive compound containing a spiropyran system. Background technique [0002] Stimuli-responsive materials are smart materials that can sense and respond to environmental changes, and are favored by researchers because of their novel functions and wide application prospects. With external stimuli, such as physical stimuli (temperature, light, ultrasound, voltage), chemical stimuli (pH, redox agents and other specific molecules such as CO 2 ) etc. The corresponding materials have aroused people's wide attention. Spiropyran (SP) is one of the most widely and deeply studied organic color-changing compounds, which can undergo a reversible structure between the colorless ring-closed spiropyran (SP) and the colored ring-opened merocyanine (MC). isomerisation. The common indoline spiropyran structure is composed of be...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K9/02
CPCC07D519/00C09K9/02
Inventor 王平伍亮成天欣陈仁杰
Owner XIANGTAN UNIV
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