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

Meso-position long chain alkyloxyphenyltetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof

A technology of chain alkoxyphenyl tetraphenanthrene ring and long-chain alkoxy aromatic aldehyde, which is applied in the field of preparation of meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivatives, which can solve the problem of porphyrin There are many synthetic steps, less synthetic research, and difficult separation, etc., to achieve the effects of high yield, simple and economical operation, and good reaction selectivity

Active Publication Date: 2016-04-13
JIANGSU RUIDA TECH CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, there are many steps in the synthesis of meso-position long-chain alkyl modification and β-position phenanthrene ring conjugated porphyrin, which are difficult and difficult to separate, so there are few studies on the synthesis of such compounds.

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
  • Meso-position long chain alkyloxyphenyltetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof
  • Meso-position long chain alkyloxyphenyltetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof
  • Meso-position long chain alkyloxyphenyltetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of compound 1a: 3,4-bis(hexadecyloxy) (1.173g, 2mmol) benzaldehyde and phenanthrene-ring conjugated pyrrole (0.572g, 2mmol) were added to a 50mL single-neck flask, and propionic acid ( 15mL) to dissolve. Under argon protection and dark conditions, the reaction was heated and refluxed for 2h. Cool to room temperature, add an appropriate amount of methanol, filter, and separate the residue by silica gel column chromatography. The eluent is dichloromethane-petroleum ether, chloroform, and then recrystallize from methanol and chloroform to obtain a dark red product. Yield: 28.0%. mp>250℃.UV-vis(CHCl 3 )λmaxnm(ε×10 -5 )583(1.319), 849(0.378)( figure 1 ); 1 HNMR (CDCl 3 )δ8.53(s, 8H), 8.34(m, 4H), 8.21-8.24(m, 4H), 7.80-7.93(m, 8H), 7.39(m, 8H), 7.20-7.23(m, 4H) , 6.98-7.04(m, 8H), 4.28-4.31(m, 8H), 4.05-4.12(m, 8H), 1.70(m, 16H), 1.45(s, 208H), 1.03-1.09(t, 24H) , 0.73(b, 2H)( figure 2 ); MALDI-TOFMASScacdforC 220 H 310 N 4 O 8 3138.84, found: 3140.28...

Embodiment 2

[0037] Synthesis of compound 1b: 3,4-bis(hexadecyloxy) (1.173g, 2mmol) benzaldehyde and phenanthrene ring conjugated pyrrole (0.572g, 2mmol) were added to a 50mL single-neck flask, and propionic acid ( 15mL) to dissolve. Under argon protection and dark conditions, the reaction was heated and refluxed for 2h. Cool to room temperature, add an appropriate amount of methanol, filter, and separate the residue by silica gel column chromatography. The eluent is dichloromethane-petroleum ether, chloroform, and then recrystallize from methanol and chloroform to obtain a dark red product. Yield: 25.3%. mp220℃.UV-vis(CHCl 3 )λmaxnm(ε×10 -5 )578(0.869), 809(0.161)( Figure 4 ); 1 HNMR (CDCl 3 )δ8.36-8.40(m, 8H), 7.80-7.83(m, 4H), 7.72-7.76(m, 12H), 7.26-7.30(m, 8H), 6.88-6.95(m, 8H), 6.60- 6.68(m, 4H), 3.92-4.01(m, 8H), 3.67-3.68(m, 4H), 3.57-3.59(m, 4H), 1.58-1.59(m, 16H), 1.30-1.32(s, 210H ), 0.90(t, 24H)( Figure 5 ); MALDI-TOFMASScacdforC 220 H 310 N 4 O 8 3138.84, found:...

Embodiment 3

[0039] Synthesis of compound 1c: The preparation method is the same as that of Example 1, yield: 321.9 mg, 30.2%. mp>250℃; UV-vis (CHCl 3 )λmaxnm(ε×10 -5 )575(0.892), 849(0.226)( Figure 7 ); 1 HNMR (CDCl 3, 500M) 58.8-8.58(m, 8H), 8.35-8.40(m, 8H), 7.66-7.73(m, 8H), 7.23(m, 8H), 7.07-7.09(m, 8H), 6.84-6.86( m, 8H), 4.13-4.17 (m, 16H), 2.28-2.35 (m, 8H), 1.86-1.88 (t, 8H), 1.66-1.69 (m, 8H), 1.54 (m, 8H), 1.38 ( s, 40H), 1.28 (t, 12H), 0.88 (b, 2H) ( Figure 8 ); MALDI-TOFMASScacdforC 144 H 150 N 4 O 12 2128.75, found: 2131.23 (M+H + )( Figure 9 ).

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 a structure and a preparation method of a porphyrin compound containing a long chain alkyloxyphenyl group and a phenanthrene ring group. The above tetraphenanthroporphyrin derivative is generated from long chain alkyloxyaryl aldehyde and phenanthrene ring conjugated pyrrole through a one-step reaction under the catalysis of propionic acid under heating refluxing conditions. The preparation method has the advantages of simple reaction steps, short reaction time, good selectivity and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivative. Background technique [0002] Porphyrins have many unique optoelectronic properties, good optical and thermal stability, and have large molar absorption coefficients in the visible light range, so they have been widely used in the fields of biochemistry, medicine, analytical chemistry, photocatalysis and materials science. It has been widely concerned and applied. In recent years, using the unique electronic structure and optoelectronic properties of porphyrin molecules, the design and synthesis of optoelectronic functional materials and the development of optoelectronic devices have become very active research fields at home and abroad. In terms of energy transfer, porphyrin molecules, as light-absorbing units in model compounds, can achieve photo-indu...

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): C07D487/22
CPCC07D487/22
Inventor 徐海军杜欣杨剑
Owner JIANGSU RUIDA TECH CO LTD
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