Microwave solid-phase method for synthesizing tetraphenylporphyrinatozinc (II)

A technology of tetrabenzoporphyrin and solid-phase synthesis, applied in the direction of organic chemistry, etc., can solve the problems of difficult separation and purification, many operation steps, long reaction time, etc., and achieves the effect of reducing cost, reducing reaction energy barrier and facilitating purification.

Active Publication Date: 2019-01-18
HUANGGANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These conventional synthetic methods have many operating steps, long reaction times and low yields.
Due to the serious sublimation of the solid direct heating metho

Method used

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  • Microwave solid-phase method for synthesizing tetraphenylporphyrinatozinc (II)
  • Microwave solid-phase method for synthesizing tetraphenylporphyrinatozinc (II)
  • Microwave solid-phase method for synthesizing tetraphenylporphyrinatozinc (II)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Microwave Synthesis of Tetrabenzoporphyrin Zn(Ⅱ)

[0026] Weigh 0.19g (18mmol) malonic acid, 0.33g (18mmol) potassium phthalimide and 0.75g (3.75mmol) zinc acetate in a mortar, mix and grind for 5min, transfer the mixed powder to a 150mL round bottom flask , the microwave power was 800W under the radiation for 5 minutes after the reaction was completed, the product was taken out, and the crude product was obtained by cooling in the dark. The crude product was separated by column chromatography to obtain the refined product. The yield was 30%.

[0027] Adopt this method to carry out synthesis, because of fast reaction speed, short reaction time, no sublimation phenomenon. The conventional method is to fully grind the raw materials, mix them uniformly, first place the powder on a quartz boat, and then put it into a quartz tube, and react at 400° C. for 60 minutes under the protection of argon, with a yield of 15%. It can be seen from the comparison that this method can...

Embodiment 2

[0029] Product map verification

[0030] Infrared Spectrum Verification: figure 1 The infrared spectrogram of the tetrabenzoporphyrin zinc (II) prepared in embodiment 1 is shown, as can be known from the analysis in the figure, 1400cm -1 ~1600cm -1 The strong absorption peaks can be attributed to the characteristic absorption peaks of C=C and C=N in the porphyrin molecule, 1340cm -1 is the C-N stretching vibration absorption peak.

[0031] UV Spectrum Verification: figure 2 The ultraviolet spectrogram of the tetrabenzoporphyrin zinc (II) prepared in Example 1 is shown, as can be seen from the analysis in the figure, there are two strong absorptions at 424nm and 623nm, wherein the strong absorption peak at 424nm is The characteristic peak of porphyrin Soret band, the absorption peak at 623nm is the Q band absorption peak.

[0032] NMR verification: 1 H NMR: 7.89(m,2H), 7.78(m,4H), 7.71(d,2H), 7.57(m,4H), 7.35(m,3H), 7.19(m,4H), 7.02(d,1H ).

[0033] From the above spec...

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Abstract

The invention discloses a microwave solid-phase method for synthesizing tetraphenylporphyrinatozinc (II). The microwave solid-phase method comprises the following preparation steps: (1) weighing malonic acid, potassium phthalimide and zinc acetate, and mixing and grinding to obtain mixed powder; (2) irradiating the mixed powder through microwaves and completely reacting to obtain a reactant; (3) after cooling the reactant in a dark place, carrying out column chromatography separation. The microwave solid-phase method has the beneficial effects that (1) reaction is carried out under a solid phase, reaction environments are wide, the limitation on reaction conditions is small and the practicality is strong; (2) microwave three-dimensional heating reaction is adopted so that the reaction timeis effectively shortened, a reaction energy barrier is reduced, no thermal sublimation occurs and the yield is improved; (3) the reaction does not need a solvent and utilization and recycling of thesolvent can be avoided so that the cost is reduced; (4) no solvent participates in the reaction and purification is facilitated.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of tetrabenzoporphyrin zinc (II). Background technique [0002] Metalloporphyrin compounds and their derivatives are a class of macrocyclic aromatic compounds containing 18r electronic structures, which are widely used in the fields of cancer diagnosis and identification, catalysis, photocells, molecular recognition, and photosensitive materials. It can also simulate physiological processes in living organisms and deal with NO in automobile exhaust x Wait. [0003] At present, the methods for synthesizing metalloporphyrin compounds include Alder synthesis method, Lindesy synthesis method, Guo Cancheng's new synthesis method and Gaode's improved new method. These conventional synthetic methods have many operating steps, long reaction times and low yields. The solid direct heating method has serious sublimation and low yield (up to 15%), and also h...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 杨水彬周庆张玉洁张雪梅
Owner HUANGGANG NORMAL UNIV
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