Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of a-π-d-π-a structure two-photon polymerization initiator and preparation method thereof

A two-photon polymerization and initiator technology, applied in organic chemistry and other fields, can solve the problems of low efficiency and insufficient mass application, and achieve the effect of short required time, simple preparation method and good microstructure precision

Active Publication Date: 2022-01-18
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, current two-photon photoinitiators are still relatively inefficient and insufficient for a large number of applications

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
  • A kind of a-π-d-π-a structure two-photon polymerization initiator and preparation method thereof
  • A kind of a-π-d-π-a structure two-photon polymerization initiator and preparation method thereof
  • A kind of a-π-d-π-a structure two-photon polymerization initiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Step one, the NaH (stored in 60% in mineral oil, 3.00g, 75mmol) was slowly added a solution containing phenothiazine (10g, 50mmol) in DMF 80mL flask, the flask containing the water bath in ice-water mixture, and stirred for 15 minutes, was slowly added 1-bromo dodecane (14.4mL, 60mmol), and the resulting solution was stirred overnight, deionized water was added slowly. after stirring for half an hour, extracted with ethyl acetate, then purified by column chromatography purification, using petroleum ether: ethyl acetate = 40: 1 (v: v) eluent, to give 10- lauryl -10H- phenothiazine, 14.33 g as a pale yellow oil, yield 78% purity 96%;

[0050] Step two, containing 10- dodecyl -10H- phenothiazine (7.35g, 20mmol) cooled to 0 ℃ 80mLDCM flask and slowly added NBS (8.9g, 50mmol), and the resulting suspension was stirred overnight, then, deionized water was slowly added and stirred for 30 minutes and then saturated brine was added and extracted to obtain an organic phase, then dried...

Embodiment 2

[0056]Step 1, NaH (3.00 g, 75 mmol) was slowly added to 80 ml of DMF solution flask containing phenothiazazine (10 g, 50 mmol), stirred, 15 minutes after stirring. 1-bromo-dodecane (14.4 ml, 60 mmol) was slowly added, and the resulting solution was stirred for 12 hours, and then deionized water was slowly added, stirred for a mixture of half an hour, extracted with ethyl acetate, then purified using a column chromatography to use oil. Ether: EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc (EtOAc)

[0057] Step Second, NBS (8.9 g, 50 mmol) was slowly added to a flask of 10-dodecyl-10H-phenothiazine (7.35 g, 20 mmol) and 80 ml DCM, cooled to 0 ° C. The resulting suspension was stirred overnight, then the deionized water was slowly added and stirred for 20 minutes, then saturated brine was added and extracted, and then dried over magnesium sulfate, filtered, remove the solvent, then column chromatography (petroleum ether: EtOAc (EtOAc)

[0058] Step three, add 3,7-dibromo-10-dodecyl-phenothiazin...

Embodiment 3

[0062] Step 1, NaH (100 mL) flask containing 3,6-dibromo-9H-carbazole (16.25 g, 50 mmol) was slowly added to 0 ° C (40% mineral oil, 4.00 g, After 15 minutes, 1-bromoate dodecane (18.0 mL, 75 mmol) was slowly added, and the resulting suspension was stirred overnight and the deionized water was slowly added, filtered and washed with petroleum ether, resulting in 3,6-two Bromo-9-dodecyl-carbazole, a gray solid 21.61 g, yield 88%, purity 96%;

[0063] Step Second, 3,6-dibromo-9-dodecyl-oxazole (4.93 g, 10 mmol), Cui (190 mg, 1 mmol), Cui (190 mg, 1 mmol), PDCl 2 (PPH 3 ) 2 (350mg, 0.5mmol), PPH 3 (262 mg, 1 mmol), 1,1-dimethyl-2-butyn-1-alcohol (2.91 mL, 30 mmol) and triethylamine (80 mL), under AR protection, the resulting mixture was refluxed to reflow at 90 ° C for 8 hours. After cooling, the solvent was removed, and the residue was poured into saturated brine and extracted with ethyl acetate (5 × 100 mL), combined with organic layers, using MgSO 4 Dry, concentrated, and used petr...

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 an A-π-D-π-A structure two-photon polymerization initiator and a preparation method thereof, comprising the following steps: step 1, the raw materials phenothiazine and 3,6-dibromo-9H-carba Azole is protected by adding dodecyl through substitution reaction; bromination reaction is carried out to phenothiazine, and para-bromine is introduced; step 2, Sonogashira coupling reaction is carried out to the result obtained in step 1, and alkyne hydroxyl group is introduced; step 3, to step 2. The product obtained is deprotected to remove the hydroxyl group; step 4, the result obtained in step 3 is subjected to Sonogashira coupling reaction, and a functional electron-withdrawing group is introduced. The optical properties and two-photon polymerization performance of the initiator of the present invention are studied, and the results show that the scanning speed of the initiator with the best performance can reach 2000 μm / s during the polymerization process under the laser power of 50mw.

Description

Technical field [0001] The present invention is in the micro and nano manufacturing field of chemical technology, particularly to an A-π-D-π-A structure of two-photon polymerization initiators preparation thereof. Background technique [0002] Two-photon effect is a third-order nonlinear effects. In 1931, Goppert-Mayer theoretically predicted molecular two-photon absorption (TPA) will occur in bright light excitation. However, until the emergence of high-energy lasers, the researchers only observed TPA phenomenon. When the light irradiation intensity reaches the order of megawatts, the material it may be two-photon absorption occurs. Since the two-photon absorption properties of a specific absorption of two photons, derived from the application of this effect on large. Photon polymerization (TPP) a three-dimensional (3D) additive manufacturing is one of the most important applications of two-photon absorption. TPA proportional to the square of the intensity of the incident light ...

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): C08F2/46C07D279/22C07D209/86
CPCC08F2/46C07D279/22C07D209/86
Inventor 张帅李尚耕徐嘉靖尹强万翔宇朱方华李娃王宇光
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com