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Synthesis method for triphyrin compound with no center coordination

A center-uncoordinated, ternary porphyrin technology, applied in the direction of organic chemistry, can solve problems such as constraints, and achieve the effects of improving synthesis yield, prolonging oxidation time, and simplifying the treatment process

Inactive Publication Date: 2014-07-16
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the highest yield of this method is about 30%, which seriously restricts the research on the synthesis of metal ternary porphyrin complexes using the central uncoordinated ternary porphyrin as a ligand.

Method used

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  • Synthesis method for triphyrin compound with no center coordination
  • Synthesis method for triphyrin compound with no center coordination
  • Synthesis method for triphyrin compound with no center coordination

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1, the synthesis and purification of tetraphenyl center uncoordinated ternary porphyrin

[0030] Step 1. At room temperature, add 1mmol of pyrrole to a 250ml single-necked flask, and then add 50ml of dry dichloromethane, 1mmol of benzaldehyde and 1.2mmol of boron trifluoride ether solution under the condition of aluminum foil to protect from light and nitrogen atmosphere. Stir at room temperature for 12 hours to obtain solution 1;

[0031] Step 2, adding 0.5 mmol of chlorobenzoquinone to solution 1, and oxidizing it at room temperature for 2 hours to obtain solution 2;

[0032] Step 3, add 1 mmol DDQ to solution 2, and oxidize for 10 hours at room temperature. Get solution three;

[0033] Step 4, add saturated sodium bicarbonate solution to solution 3 to quench the reaction, then wash the organic phase with distilled water and saturated brine respectively, and finally filter after drying with anhydrous sodium sulfate, and collect the filtrate;

[0034] Step 5...

Embodiment 2

[0037] Example 2, the synthesis and purification of four (4-fluorophenyl) center uncoordinated ternary porphyrins

[0038] Step 1. At room temperature, add 1mmol of pyrrole to a 250ml single-necked flask, and then add 50ml of dry dichloromethane, 1mmol of p-fluorobenzaldehyde and 1.2mmol of boron trifluoride ether solution . Stir at room temperature for 12 hours to obtain solution 1;

[0039] Step 2: Add 0.5 mmol of chlorobenzoquinone to solution 1, and oxidize it for 0.5 hours at room temperature to obtain solution 2;

[0040] Step 3: add 1 mmol DDQ to solution 2, and oxidize for 13 hours at room temperature. Get solution three;

[0041] Step 4, add saturated sodium bicarbonate solution to solution 3 to quench the reaction, then wash the organic phase with distilled water and saturated brine respectively, and finally filter after drying with anhydrous sodium sulfate, and collect the filtrate;

[0042] Step 5, the filtrate is rotary evaporated to dryness to obtain a residu...

Embodiment 3

[0045] Embodiment three, the synthesis and purification of four (4-methylphenyl) center uncoordinated ternary porphyrins

[0046]Step 1. At room temperature, add 1mmol of pyrrole to a 250ml single-necked flask, and then add 50ml of dry dichloromethane, 1mmol of p-tolualdehyde and 1.2mmol of boron trifluoride ether solution. Stir at room temperature for 12 hours to obtain solution 1;

[0047] Step 2: Add 0.5 mmol of chlorobenzoquinone to solution 1, and oxidize it at room temperature for 1 hour to obtain solution 2;

[0048] Step 3: add 1 mmol DDQ to solution 2, and oxidize for 12 hours at room temperature. Get solution three;

[0049] Step 4, add saturated sodium bicarbonate solution to solution 3 to quench the reaction, then wash the organic phase with distilled water and saturated brine respectively, and finally filter after drying with anhydrous sodium sulfate, and collect the filtrate;

[0050] Step 5, the filtrate is rotary evaporated to dryness to obtain a residue, a...

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Abstract

The present invention discloses a synthesis method for a triphyrin compound with no center coordination. According to the present invention, the adopted mixed oxidant is tetrachlorobenzoquinone and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, and the oxidation time is prolonged so as to significantly improve the synthesis yield of the triphyrin with no center coordination and simplify the process treatment. The synthesis method can be applied for synthesis of the triphyrin compound with no center coordination.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic macrocyclic molecules, in particular to a central uncoordinated ternary porphyrin [0002] Synthetic technology of morphine compounds. Background technique [0003] Triphyrin is a porphyrin macrocyclic compound formed by connecting three pyrrole rings and four methylene groups, and has a 14-π electronic structure. In terms of molecular structure, compared with porphyrin, the symmetry of ternary porphyrin is significantly lower, and the central ring is significantly smaller. Therefore, ternary porphyrin is also called subporphyrin (Subporphyrin). It has broad application prospects in many fields such as ion detection, sensors, solar cells, and medicine. [0004] So far, the ternary porphyrin compounds can be roughly divided into three types: the first is the ternary porphyrin compound containing a boron atom in the center. The compound is synthesized by using a compound containing ...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 薛兆历诸晓波王叶梅
Owner JIANGSU UNIV
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