Method for preparing one-class ferrocene modified porphyrin and metal porphyrin liquid crystal

A metalloporphyrin, ferrocene technology, applied in metallocene, chemical instruments and methods, organic chemistry and other directions, can solve problems such as no research reports

Inactive Publication Date: 2014-06-25
INNER MONGOLIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although both porphyrin and ferrocene-based metal-organic compounds have good liquid crystal properties, the research on porphyrin-based metal-organic liquid crystals containing ferrocene has not been reported.

Method used

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  • Method for preparing one-class ferrocene modified porphyrin and metal porphyrin liquid crystal
  • Method for preparing one-class ferrocene modified porphyrin and metal porphyrin liquid crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Series of compounds 3 Preparation of:

[0028] In a 250 mL three-neck flask equipped with a reflux condenser, add aluminum trichloride (3.5 g, 0.026 mol) and 30 mL of dichloromethane, and add long-chain n-alkyl acid chloride (0.015 mol) dropwise in an ice-water bath for 15 min. Dissolve the solution in 10 mL of dichloromethane, after dropping, continue to stir for 20 min. A solution of methyl ferrocenecarboxylate (3.0 g, 0.012 mol) dissolved in 20 mL of dichloromethane was dropped into the above system over 20 min under an ice-water bath, and the reaction was continued for 2 h after the addition was complete. Pour the reaction mixture into ice water to decompose, separate the organic phase, wash with 5% sodium carbonate solution and water successively, dry over anhydrous magnesium sulfate, and go through silica gel column chromatography with benzene as the eluent. The product is a brownish-red solid. The rate is 88%.

Embodiment 2

[0030] Series of compounds 4 Preparation of:

[0031] In a 250 mL three-neck flask, add zinc powder (13 g, 0.2 mol), wash with 4% dilute hydrochloric acid three times, pour off the supernatant, and wash with water several times. Add mercuric chloride (1.2 g, 0.017 mol) to 1 mL of concentrated hydrochloric acid to dissolve it, then add 20 mL of water to make a solution, add this solution to the above-mentioned three-neck flask and stir for 20 min to make zinc-amalgam. Methyl 1'-long chain acylferrocenecarboxylate 3 (10 mmol) was dissolved in 22 mL of benzene and 5.0 mL of methanol, added to a three-necked flask containing zinc-amalgam, heated to reflux, and 7 mL of concentrated hydrochloric acid was added dropwise, and refluxed for 3 h. Cool, filter with suction, and wash the filter cake with benzene. The organic phase was washed successively with saturated brine, 5% sodium carbonate solution and water, dried over anhydrous sodium sulfate, filtered, and evaporated to remove ...

Embodiment 3

[0033] Series of compounds 5 Preparation of:

[0034] Add sodium hydroxide (1.2 g, 0.3 mol) and 4.5 mL of water into a 50 mL round bottom flask, stir to dissolve the sodium hydroxide. Then add 4.5 mL of 1'-long-chain n-alkylferrocene formic acid methyl ester 4(7.4 mmol) ethanol solution, heated in a boiling water bath, and monitored the reaction process by thin-layer chromatography. Benzene was used as the developer. After the reaction was completed, 20 mL of water was added to dilute, extracted with ether, and the aqueous phase was adjusted to pH = 1 with dilute hydrochloric acid to precipitate out , the precipitate was dissolved in ether, washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain a reddish-brown solid with a yield of 89%.

[0035]

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Abstract

The invention relates to a method for preparing one-class ferrocene modified porphyrin and metal porphyrin liquid crystal. The method comprises the following steps: based on ferrocene methyl formate, preparing 1'-long-chain alkyl ferrocene formic acid through fourier acetoxylation acylation, Clemmensen reduction reaction and saponification, subsequently reacting the 1'-long-chain alkyl ferrocene formic acid with phosphorus trichloride to obtain 1'-long-chain alkyl ferrocene formyl chloride, and subsequently reacting the 1'-long-chain alkyl ferrocene formyl chloride with p-hydroxy benzaldehyde to obtain long-chain alkyl ferrocene substituted benzaldehyde; reacting the long-chain alkyl ferrocene substituted benzaldehyde with pyrrole to synthesize meso-tert long-chain alkyl ferrocene substituted phenyl porphyrin, and subsequently coordinating the porphyrin center with metal zinc ion to prepare metal zinc porphyrin. Due to introduction of the long-chain alkyl, the compound is both rigid and soft, and is wide in application prospect in the fields of organic photoelectric functional materials, organic semiconductor materials and liquid crystal materials.

Description

technical field [0001] The invention relates to the field of preparation of porphyrin organic liquid crystal materials, in particular to a preparation method of meso-tetra-long-chain n-alkyl ferrocene modified porphyrin and metal porphyrin. Background technique [0002] Porphyrin compounds have a delocalized two-dimensional large π electron structure, good visible light absorption and luminescence properties, and high thermal and chemical stability. They are a class of photosensitizers with excellent performance. Since porphyrins are easy to modify through peripheral substitution and central metal ion coordination, molecules with specific structures can be synthesized to adjust their electrochemical and photochemical properties, and are widely used in the fields of biology, medicine, photoelectric functional materials and devices. Connect the long-chain alkyl, alkoxy, acyloxy and amide side chains to the periphery of the porphyrin, and make the porphyrin compounds have a goo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 赵海英陈强苏敏李晴王亚光
Owner INNER MONGOLIA UNIVERSITY
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