Coumarin-porphyrin schiff base compounds and preparation method

A porphyrin Schiff base and compound technology, applied in the field of coumarin-porphyrin Schiff base compound and its preparation, can solve the problem that tetraphenylporphyrin does not have special groups, is not conducive to large-scale synthesis, and has application prospects Limitation and other issues, to avoid the separation process of column chromatography, facilitate large-scale synthesis, and improve the effect of reaction yield

Inactive Publication Date: 2009-07-29
TIANJIN UNIV
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AI Technical Summary

Problems solved by technology

[0002] Tetraphenylporphyrin itself does not have a special group, so the application prospect is limited
Although this method shortens the reaction time, post-processing is cumbersome
Also not conducive to large-scale synthesis

Method used

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  • Coumarin-porphyrin schiff base compounds and preparation method
  • Coumarin-porphyrin schiff base compounds and preparation method
  • Coumarin-porphyrin schiff base compounds and preparation method

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0018] Example 1: Preparation of 5-[4-(6-methyl-2-oxo-2H-benzopyran-4-methylimino)phenyl]-10,15,20-triphenylporphyrin (Ia)

[0019] Take 17mg (0.09mmol) of coumarin aldehyde 1 and 15mg (0.02mmol) of 5-(4-aminophenyl)-10,15,20-triphenylporphyrin in a 50mL round bottom bottle, under nitrogen protection , add processed 15mL toluene or dimethylbenzene, heat to reflux, thin plate chromatography detects, after the raw material reaction is complete, steam the toluene, use methanol / chloroform 5 / 1 (v / v) recrystallization, obtain product (Ia ) 16 mg, yield 71%. Its characterization: melting point > 300 ° C; NMR (CDCl 3 , 500MHz, δppm): -2.77 (s, 2H, NH in the porphyrin ring), 2.55 (s, 3H, methyl H), 7.03 (s, 1H, 3-position H of coumarin), 8.37 (d, J =9Hz, 1H, 8-position H of coumarin), 7.47~7.51(m, 1H, 8-position H of coumarin), 7.72~7.78(m, 11H, para- and meta-11H of porphyrin and 5-position of coumarin H), 7.92~8.04(m, 2H, porphyrin ortho-H), 8.23~8.26(m, 6H, porphyrin ortho-H), 8....

example 2

[0022] Example 2: 5-[4-(7-methoxy-2 oxygen-2H-benzopyran-4-methylimino)phenyl]-10,15,20-triphenylporphyrin (Ib) preparation

[0023] The coumarin aldehyde 1 in Example 1 is replaced by coumarin aldehyde 2, and 17mg (0.08mmol) coumarin aldehyde 2 and 15mg (0.02mmol) of 5-(4-aminophenyl)-10,15 are added, 20-triphenylporphyrin is in a 50mL round bottom bottle, and other operations are the same as in Example 1. Finally generate 5-[4-(7-methoxy-2 oxygen-2H-benzopyran-4-methylimino)phenyl]-10,15,20-triphenylporphyrin (Ib) 14mg, Yield 62%.

[0024] Melting point > 300°C.

[0025] NMR (CDCl 3 , 500MHz, δppm): -2.75 (s, 2H, NH in the porphyrin ring), 3.96 (s, 3H, methoxy H), 6.97 (d, J=10Hz, 1H, 8-position H of coumarin), 7.02~7.06(d, 1H, 6-position H of coumarin), 7.47~7.51(m, 1H, 8-position H of coumarin), 7.70~7.82(m, 11H, porphyrin para-position and meta-position 11H and coumarin 5-position H), 7.90~8.00 (m, 2H, ortho-position H of porphyrin), 8.22-8.24 (m, 6H, ortho-position...

example 3

[0028] Example 3: Preparation of 5-[4-(2-oxo-2H-naphthopyran-4-methylimino)phenyl]-10,15,20-triphenylporphyrin (Ic)

[0029] In example 1, coumarin aldehyde 1 is replaced by coumarin aldehyde 3, and 17mg (0.08mmol) coumarin aldehyde 3 and 15mg (0.02mmol) of 5-(4-aminophenyl)-10,15,20 are added -Triphenylporphyrin 1 is in the 50mL round bottom bottle, and other operations are all the same as example 1. Finally, 5-[4-(2-oxo-2H-naphthopyran-4-methylimino)phenyl]-10,15,20-triphenylporphyrin (Ic) was generated with a yield of 62%.

[0030] Melting point > 300°C.

[0031] NMR (CDCl 3 , 500MHz, δppm): -2.75 (s, 2H, NH in the porphyrin ring), 7.72~7.82 (m, 15H, porphyrin ortho-para H and coumarin 3, 5, 6, 8 H), 7.97~ 8.05(m, 2H, porphyrin ortho-H), 8.22~8.24(m, 7H, porphyrin ortho-H and coumarin 7-position H), 8.68~8.75(m, 2H, coumarin 9, 10-position H ), 8.86~8.90 (m, 8H, 2-position H of porphyrin), 8.945 (s, 1H, -C=NH position H).

[0032] ESI-MS m / z 836.4(M+H) + (calcd.for C ...

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Abstract

The invention relates to a coumarin-porphyrin Schiff alkali compound and a preparation method thereof. 5-(4-aminophenyl)-10, 15, 20-triphenyl porphyrin and coumarin aldehyde are dissolved in inertia solvent and heated until refluxing under the protection of nitrogen. A thin-layer chromatography is used for monitoring the reaction liquid. After the 5-(4-aminophenyl)-10, 15, 20-triphenyl porphyrin reacts fully, the reaction is stopped. Decompression is carried out for steaming out the solvent. After the recrystal purification, corresponding coumarin-porphyrin Schiff alkali is obtained. With the structure shown in formula (I), the porphyrin Schiff alkali compound has the advantages of high yield and simple separation and purification, and the product yield can reach 60-70 percent.

Description

technical field [0001] The invention relates to a coumarin-porphyrin Schiff base compound and a preparation method thereof. Background technique [0002] Tetraphenylporphyrin itself does not have special groups, so its application prospects are limited. However, there are many active sites on the core of tetraphenylporphyrin, and if it is connected with other groups with special structures, its spectral response can be changed. [0003] In recent years, people have made rapid progress in the research on the modification of tetraphenylporphyrin at different positions. Complex systems have been constructed through the reaction of the middle phenyl group of porphyrin and the reaction of porphyrin β position. In particular, the introduction or conversion of functional groups on the benzene ring of tetraphenylporphyrin is a very important porphyrin modification method. [0004] Schiff base compounds are formed by condensation of aldehydes or ketones with ammonia or amines. As a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07D311/18C07D311/92
Inventor 冯亚青李成杰汪磊刘秀军
Owner TIANJIN UNIV
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