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a kind of a 3 B-type monomercapto porphyrin compound and its preparation method and use

A single thiol porphyrin, A3B technology, used in organic chemistry, pharmaceutical formulations, drug combinations, etc., can solve problems such as easy agglomeration, and achieve the effects of overcoming insoluble in water, retaining photosensitivity, good dispersibility and stability.

Inactive Publication Date: 2020-09-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] For the problems existing in the above-mentioned prior art, the object of the present invention is to provide a kind of A 3 B-type monomercapto porphyrin compound and its preparation method and application, the monomercapto porphyrin prepared by the method of the present invention has a strong coordination ability, and the compound is combined with UiO-66 through a post-modification synthesis method to prepare monomercapto porphyrin modified Framework nanomaterials, namely UiO-66-H 2 TClPP-(SH) 1 , UiO-66-H prepared by the present invention 2 TClPP-(SH) 1 It can well overcome the problems of poor solubility in water, easy aggregation and poor stability of porphyrin molecular compounds in the prior art, so that the quantum yield, fluorescence lifetime and photosensitivity of porphyrin and its derivatives can be improved. greatly improved

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  • a kind of a <sub>3</sub> B-type monomercapto porphyrin compound and its preparation method and use
  • a kind of a <sub>3</sub> B-type monomercapto porphyrin compound and its preparation method and use
  • a kind of a <sub>3</sub> B-type monomercapto porphyrin compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] A 3 Preparation of B-type monomercapto porphyrin H2TCLPP-(SH)1:

[0075] (1)H 2 TClPP-(COOH) 1 Preparation of:

[0076] Mix p-chlorobenzaldehyde (7.0g, 0.050mol), p-formylbenzoic acid (1.5g, 0.010mol) and 200mL propionic acid, stir to dissolve, heat to reflux (145°C), and mix 50mL propionic acid and pyrrole ( 4.5mL, 0.065mol) was added dropwise to the mixture, and continued to reflux for 0.5h after the dropwise addition.

[0077] Then, cool to room temperature naturally, add 200mL methanol / water mixed solution (V 甲醇 :V 水 =95:5), placed in the refrigerator overnight.

[0078] Finally, filter with suction, wash the filter cake with water and methanol until the filtrate is light red, and dry naturally. The product is firstly separated by silica gel column chromatography with dichloromethane as eluent, and the first product collected is tetrachlorophenylporphyrin H 2 TClPP. Then use dichloromethane instead: anhydrous methanol=10:1 as eluent, separate by silica gel ...

Embodiment 2

[0090] A 3 B-type monomercaptoporphyrin H 2 TCLPP-(SH) 1 Preparation of:

[0091] (1)H 2 TClPP-(COOH) 1 The preparation method is with embodiment 1.

[0092] (2)H 2 TClPP-(SH) 1 Preparation of:

[0093] H 2 TClPP-(COOH) 1 (76mg, 0.10mmol) was dissolved in 10mL of dry dichloromethane, and then SOCl 2 (5mL, 0.069mol) was slowly added dropwise to the mixed solution, and after reflux (45°C) for 5h, the excess SOCl was distilled off under normal pressure 2 and dichloromethane to obtain porphyrinyl chloride H as a black-green solid 2 TClPP-(COCl) 1 . 75 mg H 2 TClPP-(COCl) 1 Dissolve in 15 mL of dried THF to obtain the first reaction solution.

[0094] 1,2-Dimercaptoethane (168 μL, 2.0 mmol) and triethylamine (40 μL, 0.29 mmol) were dissolved in 15 mL of dry THF to obtain a second reaction solution.

[0095] The first reaction solution was added dropwise to the second reaction solution at room temperature and protected from light at a rate of 3 seconds / drop, and the...

Embodiment 3

[0098] A 3 B-type monomercaptoporphyrin H 2 TClPP-(SH) 1 Preparation of:

[0099] (1)H 2 TPP-(COOH) 4 The preparation method is with embodiment 1.

[0100] (2)H 2 TClPP-(SH) 1 Preparation of:

[0101] H 2 TClPP-(COOH) 1 (96mg, 0.13mmol) was dissolved in 6mL of dry dichloromethane, and then SOCl 2 (6mL, 0.083mol) was slowly added dropwise to the mixed solution, and after reflux (40°C) for 4h, the excess SOCl was distilled off under normal pressure 2 and dichloromethane to obtain porphyrinyl chloride H as a black-green solid 2 TClPP-(COCl) 1 . 100 mg H 2 TClPP-(COCl) 1 Dissolve in 15 mL of dried THF to obtain the first reaction solution.

[0102] A second reaction solution was obtained by dissolving 1,2-dimercaptoethane (126 μL, 1.5 mmol) and triethylamine (40 μL, 0.29 mmol) in 12.5 mL of dry THF.

[0103] The first reaction solution was added dropwise to the second reaction solution under the condition of normal temperature and light avoidance, and the rate of ...

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Abstract

The invention relates to the field of functional coordination compounds, and concretely relates to an A3B type monothiol porphyrin compound as well as a preparation method and application thereof. Themonothiol porphyrin compound prepared through the method provided by the invention has a strong coordination ability; the compound and UiO-66 is synthesized through a post-modification synthesis method so as to prepare a frame nanometer material modified by monothiol porphyrin, i.e., UiO-66-H2TC1PP-(SH)1. The UiO-66-H2TC1PP-(SH)1 prepared by the invention can well solve the problems that a porphyrin molecular compound in the prior art is insoluble in water, easy to agglomerate and poor in stability, so that the quantum yield, the fluorescent lifetime and a light sensitive characteristic of singlet oxygen of porphyrin and derivatives thereof are greatly improved.

Description

technical field [0001] The invention relates to the field of functional complexes, in particular to a kind of A 3 B-type monomercapto porphyrin compound and its preparation method and application. Background technique [0002] Porphyrin compounds are a class of macrocyclic conjugated molecules that widely exist in nature and have special physiological activities. Chlorophyll and heme are typical representatives, and they both play important roles in organisms. The artificially synthesized porphyrin molecules are mainly substituted at the meso-position (middle position) by various types of functional groups, and the number and arrangement of substituent groups are various. They can be simply divided into symmetrical porphyrin compounds and asymmetric porphyrin compounds. At present, the meso-position of the reported asymmetric porphyrin compounds is mainly composed of two different substituent groups (represented by A and B), which are divided into AABB, ABAB and A 3 Type B...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C07D487/22A61K41/00A61P35/00
Inventor 董育斌姜嫄阚京兰
Owner SHANDONG NORMAL UNIV
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