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Bay-position oxygen-intercalation aza-heptatomic ring 3, 4:9, 10-perylene tetracarboxylic acid butyl acetate and synthesis method thereof

A technology of perylene tetracarboxylic acid and synthesis method, which is applied in the direction of organic chemistry, can solve the problems such as the difficulty in the synthesis of perylene compounds with seven-membered rings, and achieve the effects of high yield, mild reaction conditions, and good photophysical properties

Inactive Publication Date: 2015-09-30
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the seven-membered ring is not a common stable structure, there are certain difficulties in the synthesis of the related bay-positioned seven-membered ring perylene compounds, so the bay-positioned seven-membered ring perylene compound is rare, but the new bay-positioned seven-membered ring perylene Since the oxygen and nitrogen atoms with strong electron-donating ability are connected on the same side of the bay position, the electronic structure of the target compound can be changed to a large extent, and it has good photophysical properties. Based on this, it is urgent to provide a A new method for the synthesis of perylene-based compounds with seven-membered rings at the Bay position, providing a new idea for the cyclization reaction of perylene-based derivatives

Method used

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  • Bay-position oxygen-intercalation aza-heptatomic ring 3, 4:9, 10-perylene tetracarboxylic acid butyl acetate and synthesis method thereof
  • Bay-position oxygen-intercalation aza-heptatomic ring 3, 4:9, 10-perylene tetracarboxylic acid butyl acetate and synthesis method thereof
  • Bay-position oxygen-intercalation aza-heptatomic ring 3, 4:9, 10-perylene tetracarboxylic acid butyl acetate and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 100 ml round bottom flask, add 1-amino-12-hydroxyl-3,4:9,10-perylenetetracarboxylic acid n-butyl ester (200 mg, 0.29 mmol), paraformaldehyde (60 mg, 2.0 mg mol), dehydrated ethanol (50 milliliters), reacted for 12 hours at 78 degrees Celsius. After the reaction was completed, it was cooled to room temperature, and the solvent was removed to obtain a crude product. The crude product was purified by column chromatography (silica gel 200-300 mesh, eluent dichloromethane: ethyl acetate = 20:1 (volume ratio)) to obtain 123 mg of a red solid, which is compound A (structurally characterized as figure 1 with 2 ), yield 61%. 1 H-NMR (300MHz, CDCl 3 ,ppm):δ=8.16(d,J=6.0Hz,2H),7.96(d,J=9Hz,1H),7.89(d,J=9Hz,1H),7.80(s,1H),7.52(s ,1H),5.98(t,J=7.3Hz,1H),5.02(d,J=7.3Hz,2H),4.34-4.28(m,8H),1.80-1.73(m,8H),1.53–1.46( m,8H),1.02-0.98(m,12H).MS(MALDI-TOF):m / z=696.3168(M + ).

[0038] The paraformaldehyde was purchased from Sinopharm Chemical Reagent Co., Ltd., product number ...

Embodiment 2

[0046] In a 50 ml round bottom flask, add 1-amino-12-hydroxyl-3,4:9,10-perylenetetracarboxylic acid n-butyl ester (200 mg, 0.29 mmol), pyridine-2-carbaldehyde (107 mg, 1 mmol), tetrahydrofuran (20 ml), and reacted at 65 degrees Celsius for 48 hours. After the reaction was completed, it was cooled to room temperature, and the solvent was removed to obtain a crude product. The crude product was purified by column chromatography (silica gel 200-300 mesh, eluent dichloromethane: ethyl acetate = 20:1 (volume ratio)), and 117 mg of a red solid was obtained, which was compound B (structural characterization as image 3 with 4 ), yield 52%.1 H-NMR (300MHz, CDCl 3 ,ppm): δ=8.73(d,J=6.0Hz,1H),8,28(d,J=3Hz,1H),8.25(d,J=3Hz,1H),8.05(d,J=7.8Hz ,1H),7.96-7.93(m,3H),7.84-7.81(m,2H),7.74(d,J=7.8Hz,1H),4.35-4.29(m,8H),1.79-1.75(m,8H ),1.52–1.43(m,8H),1.03-0.96(m,12H).MS(MALDI-TOF):m / z=773.3508(M + ).

[0047] The source of the 1-amino-12-hydroxyl-3,4:9,10-perylenetetracarboxylic acid n-b...

Embodiment 3

[0054] In a 50 ml round bottom flask, add 1-amino-12-hydroxyl-3,4:9,10-perylenetetracarboxylic acid n-butyl ester (200 mg, 0.29 mmol), 8-hydroxyquinoline-2-formaldehyde (173 mg, 1 mmol), 1,4-dioxane (30 ml), reacted at 80°C for 10 hours. After the reaction was completed, it was cooled to room temperature, and the solvent was removed to obtain a crude product. The crude product was purified by column chromatography (silica gel 200-300 mesh, eluent dichloromethane: ethyl acetate = 20:1 (volume ratio)), and 103 mg of red solid was obtained, which was compound C (structural characterization as Figure 5 with 6 ), yield 55%. 1 H-NMR (300MHz, CDCl 3 , ppm): δ=8.36(d, J=9.0Hz, 1H), 8.30(s, 1H), 8.10-8.05(m, 2H), 7.97(d, J=9Hz, 1H), 7.84-7.81(m ,2H),7.75(d,J=9Hz,1H),7.62-7.56(m,2H),7.46(d,J=9Hz,1H),7.34(d,J=6Hz,1H),5.76(d, J=6Hz, 1H), 5.02(d, J=7.3Hz, 2H), 4.44-4.31(m, 8H), 1.89-1.77(m, 8H), 1.53–1.40(m, 8H), 1.07-1.02( m,12H).MS (MALDI-TOF): m / z=839.3389 (M + ).

[0055] The ...

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Abstract

The invention discloses bay-position oxygen-intercalation aza-heptatomic ring 3, 4:9, 10-perylene tetracarboxylic acid butyl acetate and a synthesis method thereof. 1-amino-12-hydroxy-3, 4:9, 10-perylene tetracarboxylic acid butyl acetate is dissolved in an organic solvent, aldehyde substances are added and react at the temperature of 60 DEG C-80 DEG C for 10 hours-60 hours through stirring, the organic solvent is removed after reaction is completed, and the product can be obtained through separation and purification. The reaction condition is mild, the reaction steps are simple, and the yield is high and is above 50%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a n-butyl perylenetetracarboxylic acid 3,4:9,10-perylenetetracarboxylate and a synthesis method thereof. Background technique [0002] The π-conjugated system has strong absorption and emission properties, and has a wide range of applications in the fields of organic photovoltaics, nonlinear optics, and functional bioimaging. As a member of the π-conjugated system, perylene derivatives have good planar It has the advantages of high charge mobility, high quantum yield, and photothermal stability, and has attracted much attention from researchers. [0003] Perylene compounds can easily tune the photophysical properties of perylene compounds through the ring expansion reaction. Perylene compounds with five-membered rings and six-membered rings fused in the bay position are very common and have good photoelectric properties. more mature. However, since the sev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/06
CPCC07D267/06
Inventor 石志强李教富
Owner SHANDONG NORMAL UNIV
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