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

Preparation method of light-driven molecular motor based on oxidized benzofuran structure

A technology of light-driven molecules and molecular motors, which is applied in the preparation of carbon-based compounds, the preparation of organic compounds, and the preparation of aminohydroxy compounds, etc., can solve the problems of degradation, incompatible wavelengths, low pollution and convenience, and achieves less waste, less waste, The effect of low environmental pollution

Active Publication Date: 2021-12-24
HUBEI UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are some limitations in light-activated methods, some molecular motors may irreversibly degrade after long-term exposure, or they require wavelengths that are not compatible with the local environment, etc.; however, light-driven molecular motors are less polluted by light. Sex and the convenience of light still attract the attention of light-driven molecular motor researchers
[0005]Currently, light-activated organic molecular motors still cannot achieve the efficiency and complexity of their chemically driven biological counterparts, and further optimization design is still needed to develop more efficient molecular motors and its synthesis method

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 method of light-driven molecular motor based on oxidized benzofuran structure
  • Preparation method of light-driven molecular motor based on oxidized benzofuran structure
  • Preparation method of light-driven molecular motor based on oxidized benzofuran structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Synthesis of Compound 4: Add AlCl to a 100mL flask under nitrogen protection 3 (8g, 0.06mol, 2.0eq.) and nitrobenzene (PhNO 2 , 25mL), stirred until dissolved, then added succinic anhydride (3g, 0.03mol, 1.0eq.) and naphthalene (5.8g, 0.045mmol, 1.5eq.), stirred at room temperature overnight. After the TLC detection reaction was completed, ice water (20mL) and 6mol / L hydrochloric acid (5mL) were added, and a pale yellow precipitate was precipitated. The mixture was filtered, and the filter cake was rinsed 3 times with n-hexane (30mL) and water (30mL) (10mL ×3). Toluene (20 mL) was added to a 100 mL single-necked bottle containing the above filter cake, heated to 65° C. and stirred for 0.5 h, cooled to 35° C., filtered, and rinsed with a little toluene to obtain compound 4 (off-white solid, 2.54 g). The rate is 37%. 1 H NMR (400MHz, CDCl 3 )δ8.52(s,1H),8.05(d,J=8.4Hz,1H),7.97(d,J=8.0Hz,1H),7.89(t,J=8.6Hz,2H),7.61(t, J=7.2Hz, 1H), 7.56(t, J=7.4Hz, 1H), 3.47(t, J=6.6H...

Embodiment 2

[0079] Synthesis of Molecular Motor 1: Under the protection of nitrogen, add compound 2 (100mg, 0.47mmol, 1.0eq) and anhydrous THF (3mL) into a 25mL two-necked flask, cool to 0°C, add titanium tetrachloride (TiCl 4 , 0.1mL, 0.7mmol, 1.5eq), the dropwise addition was completed and stirred for 5min, then added 2-coumaranone 3 (95mg, 0.7mmol, 1.5eq) dissolved in THF (2mL) and 1,8-di Azabicycloundec-7-ene (DBU, 0.15 mL, 0.7 mmol, 1.5 eq). Wait until it rises to room temperature and react for 5h. Add 10 mL of hydrochloric acid (1mol / L) to the reaction mixture to quench, extract with ethyl acetate (50 mL×3), combine the organic phases, wash with saturated brine and dry over anhydrous sodium sulfate, and concentrate the organic phases under reduced pressure to obtain a reddish-brown oily substance, crude Motor 1 (yellow solid, 118 mg) was separated by thin layer chromatography with a yield of 76%. 1 H NMR (400MHz, CDCl 3 )δ7.94-7.92(m,2H),7.71(d,J=8.4Hz,1H),7.47-7.44(m,2H),7.36-7....

Embodiment 3

[0081] The light-driven process of molecular motor 1: when (P)-(S)-stable E-1 is irradiated with a 365nm light source, it will cause photoisomerization of the double bond in the middle of the axis, and generate (M)-(S)-unstable Z-1, which can undergo irreversible thermally induced helical inversion (THI) at room temperature (25°C) to form (P)-(S)-stable Z-1, completes the first 180° rotation. Similarly, (P)-(S)-stable Z-1 was irradiated with a 365 nm light source to form (M)-(S)-unstable E-1, which undergoes irreversible thermally induced helical inversion (THI) at 80 °C and then Obtain initial (P)-(S)-stable E-1. After the second rotation cycle is completed, the upper half of the motor completes a 360° unidirectional rotation relative to the lower half.

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 relates to a preparation method and application of a molecular motor containing an oxidized benzofuran structure, and belongs to the technical field of organic chemistry. A first motor takes 3-methyl-2,3-dihydrophenanthren-4(1H)-one and 2-coumaranone as raw materials, a second motor takes 3-methyl-2,3-dihydrophenanthren-4(1H)-one and naphtho[1,2-b]furan-2(3H)-one as raw materials, a third motor takes 3-methyl-2,3-dihydrophenanthren-4(1H)-one and 6-isopropylbenzofuran-2(3H)-one as raw materials, in the presence of titanium tetrachloride and 1,8-diazabicyclo[5.4.0]undec-7-ene and in an anhydrous tetrahydrofuran solvent, nucleophilic addition reaction is performed to prepare the molecular motor containing the oxidized benzofuran structure. The method has the advantages of mild reaction conditions, no need of adding strong acid and strong alkali, low requirements on equipment and reduction of the operation cost; few three wastes are generated in the reaction process, and the environmental pollution degree is low; and the obtained product motor is novel in structure and has potential application value in the field of molecular devices.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a series of preparation methods of benzofuran molecular motor compounds. Background technique [0002] Molecular motors are molecules that move their submolecular components in a well-defined and controllable manner in response to specific stimuli to generate mechanical work. Generating mechanical work and controlled motion at the nanoscale is very important and prospective. At this level, molecular motors are in equilibrium with the ubiquitous thermal noise from surrounding molecules and must resist the effects of this Brownian motion. Thus, viscous forces are many orders of magnitude stronger than inertial forces, and the laws and physics used by macroscopic motors do not apply at the molecular level. Molecular motors must therefore employ different mechanisms to absorb energy and thereby complete a mechanical cycle that drives them away from thermal equilibrium in a ...

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 Applications(China)
IPC IPC(8): C07D307/83C07D307/92C07C51/09C07C59/84C07C51/347C07C57/30C07C45/45C07C49/675C07C41/16C07C43/225C07C41/24C07C43/20C07C213/06C07C213/08C07C217/84
CPCC07D307/83C07D307/92C07C51/09C07C51/347C07C45/455C07C41/16C07C41/24C07C213/06C07C213/08C07C59/84C07C57/30C07C49/675C07C43/225C07C43/20C07C217/84
Inventor 彭芬张臣李全曾明华
Owner HUBEI UNIV
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