Preparation and application of optical switch spiropyran-peryleneimide compound

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

Active Publication Date: 2021-08-10
HUNAN UNIV OF SCI & TECH
View PDF6 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation and application of optical switch spiropyran-peryleneimide compound
  • Preparation and application of optical switch spiropyran-peryleneimide compound
  • Preparation and application of optical switch spiropyran-peryleneimide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0060] (1) Add 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride (535 mg, 1.0 mmol) and diglycolamine (263 mg, 2.5 mmol) to Into a 25 mL two-neck round bottom 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 PDI-DGA (675 g, 96%) as a red solid.

[0061] (2) Dissolve the compound PDI-DGA (30 mg, 0.04 mmol) in 5 mL of anhydrous dichloromethane, and add N-carboxyethyl-3,3-dimethyl-6'- Nitroindoline spiropyran (40 mg, 0.08 mmol), N,N'-diisopropylcarbodiimide (9 μL, 0.06 mmol), and 4-dimethylaminopyridine (2.3 mg, 0.02 mmol) After the dropwise addition, turn to room temperature and stir the reaction for 24 hours. After the reaction was complete...

Embodiment 2

[0062] Embodiment 2: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0063] Dissolve the compound PDI-DGA (30 mg, 0.04 mmol) obtained in Example 1 (1) in 5 mL of anhydrous DCM, place at 0°C and add 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 for 24 hours. After the reaction was completed, the resulting mixture was concentrated and then purified by column using dichloromethane and anhydrous methanol (v:v = 100:1) as eluents to obtain a red solid SP-PDI (45 mg, 75%);

Embodiment 3

[0064] Embodiment 3: The preparation of a symmetrically substituted optical switch spiropyran-peryleneimide compound, the specific steps are as follows:

[0065] Dissolve the compound PDI-DGA (30 mg, 0.04 mmol) obtained in Example 1 (1) in 5 mL of anhydrous DCM, place at 0°C and add 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 for 24 hours. After the reaction was complete, 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 (42 mg, 70%);

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses the preparation and application of an optical switch spiropyran-peryleneimide compound. The method synthesizes a symmetrically or asymmetrically substituted spiropyran-peryleneimide compound, which is introduced by a one-step miniemulsion polymerization method In the polymer nanoparticle system, a photoswitchable fluorescent polymer nanoparticle was prepared. The nanoparticles can exhibit fast-response fluorescent switching properties under the irradiation of ultraviolet light and visible light in the state of solution and solid film. Compared with the existing optical switch fluorescent polymer nanoparticles, the optical switch fluorescent polymer nanoparticles obtained in the present invention are connected to acceptor groups in the form of covalent bonds, reducing the use of acceptors, and the input cost is lower , simple synthesis route and other advantages, suitable for large-scale synthesis and practical production applications, and has great application prospects in technical fields such as display materials.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap