Preparation method and application of photoswitch spiropyran-perylene imide compound

A perylene imide and compound technology, which is applied in the preparation and application field of optical switch spiropyran-perylene imide compound, can solve the problems of poor solubility, synthesis and application limitations, etc., reduce the amount of use, and benefit The effect of large-scale industrial production and huge application prospects

Active Publication Date: 2019-06-28
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Peryleneimide derivatives have good molecular planarity, so the interaction of intermolecular π bonds is greatly enhanced, and has a large lattice energy, which leads to the poor solubility of most peryleneimide compounds, making their synthesis and Application is limited to some extent, so it needs to be chemically modified to improve its solubility

Method used

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  • Preparation method and application of photoswitch spiropyran-perylene imide compound
  • Preparation method and application of photoswitch spiropyran-perylene imide compound
  • Preparation method and application of photoswitch spiropyran-perylene imide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0059] (1) Add 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride (535mg, 1.0mmol) and diglycolamine (263mg, 2.5mmol) into two ports of 25mL In the round-bottomed flask, add 20 mL of dry pyridine and stir to dissolve, then reflux for 3 hours. After the reaction was completed, the solvent was concentrated, precipitated in petroleum ether, centrifuged, and dried in vacuo to obtain red solid PDI-DGA (675 g, 96%).

[0060] (2) Dissolve the compound PDI-DGA (30mg, 0.04mmol) in 5mL of anhydrous dichloromethane, place at 0°C and add N-carboxyethyl-3,3-dimethyl-6'-nitro Indoline spiropyran (40 mg, 0.08 mmol), N,N'-diisopropylcarbodiimide (9 μL, 0.06 mmol) and 4-dimethylaminopyridine (2.3 mg, 0.02 mmol), added dropwise Then turn to room temperature and stir for 24 hours. After the reaction was completed, the resulti...

Embodiment 2

[0061] Embodiment 2: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0062] The compound PDI-DGA (30 mg, 0.04 mmol) obtained in Example 1 (1) was dissolved in 5 mL of anhydrous DCM, placed at 0° C., and N-carboxyethyl-3,3-dimethyl-6 '-Nitroindoline spiropyran (80 mg, 0.16 mmol), N,N'-diisopropylcarbodiimide (12 μL, 0.08 mmol) and 4-dimethylaminopyridine (3.7 mg, 0.03 mmol) After the dropwise addition, turn to room temperature and stir the reaction for 24 hours. After the reaction was completed, the resulting mixture was concentrated and then purified by using dichloromethane and anhydrous methanol (v:v=100:1) as eluents for column purification. After vacuum drying, a red solid SP-PDI (45mg, 75 %);

Embodiment 3

[0063] Embodiment 3: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0064] The compound PDI-DGA (30 mg, 0.04 mmol) obtained in Example 1 (1) was dissolved in 5 mL of anhydrous DCM, placed at 0° C., and N-carboxyethyl-3,3-dimethyl-6 '-Nitroindoline spiropyran (100 mg, 0.2 mmol), N,N'-diisopropylcarbodiimide (14 μL, 0.1 mmol) and 4-dimethylaminopyridine (4.9 mg, 0.04 mmol) After the dropwise addition, turn to room temperature and stir the reaction for 24 hours. After the reaction was completed, the resulting mixture was concentrated and purified by column purification using dichloromethane and anhydrous methanol (v:v=100:1) as eluents to obtain a red solid SP-PDI (42mg, 70 %);

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Abstract

The invention discloses a preparation method and application of a photoswitch spiropyran-perylene imide compound. By means of the method, the symmetric or asymmetric substituted spiropyran-perylene imide compound is synthesized and introduced into a polymer nanoparticle system through a one-step fine emulsion polymerization method to prepare a photoswitch fluorescent polymer nanoparticle. The nanoparticle can show fluorescent switching performance with high response speed under the irradiation of ultraviolet light and visible light in a solution state or a solid film state. Compared with existing photoswitch fluorescent polymer nanoparticles, the obtained photoswitch fluorescent polymer nanoparticle has the advantages that through connection to an acceptor group in the form of covalent bonds, the usage quantity of acceptors is reduced, the investment cost is low, and the synthesis route is simple. The compound is suitable for amplification synthesis and practical production applicationand has a great application prospect in the technical fields of display materials and the like.

Description

technical field [0001] The invention belongs to the technical fields of preparation of chemical materials, preparation of photoelectric energy conversion materials, and photoelectric energy conversion materials, especially optical switch fluorescent polymer nanoparticles based on spiropyran-peryleneimide compounds, preparation methods and applications, specifically, Involving the synthesis of symmetrically substituted photoswitchable spiropyran-perylimide compounds and asymmetrically substituted photoswitchable spiropyran-perylimide compounds and photoswitchable fluorescent polymers based on spiropyran-perylimide compounds Preparation and application of nanoparticles. Background technique [0002] Spiropyran compounds are a very important class of organic photoswitching compounds, which are currently the most researched and most widely used. The indoline ring and the benzopyran ring in the molecule are connected through the spiro carbon atom at the center, so the two rings ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K9/02C08F220/14C08F220/36C08F222/14C08J5/18C08L33/12
Inventor 陈建余茂林王涵王宏张培盛张崇华
Owner HUNAN UNIV OF SCI & TECH
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