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A meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivative and its preparation method

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

Active Publication Date: 2018-01-05
JIANGSU RUIDA TECH CO LTD
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  • 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

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  • A meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivative and its preparation method
  • A meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivative and its preparation method
  • A meso-position long-chain alkoxyphenyl tetraphenanthrene ring conjugated porphyrin derivative and its preparation method

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 in a 50mL single-necked bottle, and propionic acid ( 15mL) for dissolution. Under the protection of argon and dark conditions, the reaction was heated to reflux for 2 h. Cool to room temperature, add an appropriate amount of methanol, filter, the residue is separated by silica gel column chromatography, the eluent is dichloromethane-petroleum ether, chloroform, and then recrystallized by methanol and chloroform to obtain a dark red product. Yield: 28.0%. mp>250℃.UV-vis(CHCl 3 )λmax nm(ε×10 -5 )583(1.319), 849(0.378)( figure 1 ); 1 H NMR (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-TOF MASS cacd for C 220 h 310 N 4 o 8 3138....

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 in a 50mL single-necked bottle, and propionic acid ( 15mL) for dissolution. Under the protection of argon and dark conditions, the reaction was heated to reflux for 2 h. Cool to room temperature, add an appropriate amount of methanol, filter, the residue is separated by silica gel column chromatography, the eluent is dichloromethane-petroleum ether, chloroform, and then recrystallized by methanol and chloroform to obtain a dark red product. Yield: 25.3%. mp 220℃.UV-vis(CHCl 3 )λmax nm(ε×10 -5 )578(0.869), 809(0.161)( Figure 4 ); 1 H NMR (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-TOF MASS cacd for C 220 h 310 N...

Embodiment 3

[0039] Synthesis of Compound 1c: The preparation method is the same as in Example 1, and the yield: 321.9mg, 30.2%. mp>250℃; UV-vis(CHCl 3 )λmax nm(ε×10 -5 )575(0.892), 849(0.226)( Figure 7 ); 1 H NMR (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-TOF MASS cacd for C 144 h 150 N 4 o 12 2128.75, found: 2131.23 (M+H + )( Figure 9 ).

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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] Porphyrin compounds have many unique photoelectric properties, good light and thermal stability, and have a large molar absorptivity in the visible light range, so they have been widely used in biochemistry, medicine, analytical chemistry, photocatalysis, and material science. It has received extensive attention and application. In recent years, using the unique electronic structure and photoelectric properties of porphyrin molecules, the design and synthesis of photoelectric functional materials and the development of photoelectric 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 realize light-induced charg...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 徐海军杜欣杨剑
Owner JIANGSU RUIDA TECH CO LTD
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