Serial compounds with triptycene as framework and in bridge connection with metalloporphyrin through pyrene tetrone and preparation method therefor

A technology of metalloporphyrin and pyrenetetrane bridge, which is applied in the field of photoelectric conversion materials, can solve the problems of general poor solubility, multiple by-products, difficult separation and purification, etc.

Inactive Publication Date: 2016-01-20
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on porphyrin is currently mainly aimed at modifying tetraphenylporphyrin, but the general solubility is not good, and more by-products are easily generated during the modification process, which is difficult to separate and purify.
Molecular links are mainly realized through amide bonds, acid anhydride bonds and adipic acid, which have a relatively large impact on the planarity of molecules, and are not conducive to electron transfer, thus affecting its photoelectric effect.

Method used

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  • Serial compounds with triptycene as framework and in bridge connection with metalloporphyrin through pyrene tetrone and preparation method therefor
  • Serial compounds with triptycene as framework and in bridge connection with metalloporphyrin through pyrene tetrone and preparation method therefor
  • Serial compounds with triptycene as framework and in bridge connection with metalloporphyrin through pyrene tetrone and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The preparation method of pyrenetetraone bridged triptycene-copper porphyrin comprises the steps:

[0073] (1) Synthesis of 2,6,14-trinitrotriptycene

[0074] Add 200ml of concentrated nitric acid and 5g of triptycene to a 500mL round bottom flask in turn, stir, heat to 65°C, reflux for 12-24h under stirring, add water and stir after cooling to room temperature, filter the precipitate with a Buchner funnel, and wash with water for two time, vacuum-dried to obtain a pale yellow solid; use 200-300 mesh silica gel to pass through the column, the eluent is ethyl acetate:petroleum ether=1:3, collect the product of the third band, and obtain 2,6,14-trinitro Triptycene compound 0.8g, yield 33%.

[0075] (2) Synthesis of 2,6,14-triaminotriptycene

[0076] Add 50ml of dichloride, 0.8g of 2,6,14-trinitrotriptycene, 1.65g of sodium borohydride and 0.2g of palladium / carbon (5%) to a 250ml pear-shaped bottle, and react for 1 to 2 hours under nitrogen protection , add 10ml of meth...

Embodiment 2

[0099] The preparation method of pyrenetetraone bridged triptycene-nickel porphyrin compound comprises the steps:

[0100] (1) Synthesis of 2,6,14-trinitrotriptycene

[0101] Add 200ml of concentrated nitric acid and 5g of triptycene to a 500mL round bottom flask in turn, stir, heat to 65°C, reflux for 12-24h under stirring, add water and stir after cooling to room temperature, filter the precipitate with a Buchner funnel, and wash with water for two time, vacuum-dried to obtain a pale yellow solid; use 200-300 mesh silica gel to pass through the column, the eluent is ethyl acetate:petroleum ether=1:3, collect the product of the third band, and obtain 2,6,14-trinitro Triptycene compound 0.8g, yield 33%.

[0102] (2) Synthesis of 2,6,14-triaminotriptycene

[0103] Add 50ml of dichloride, 0.8g of 2,6,14-trinitrotriptycene, 1.65g of sodium borohydride and 0.2g of palladium / carbon (5%) to a 250ml pear-shaped bottle, and react for 1 to 2 hours under nitrogen protection , add 10m...

Embodiment 3

[0119] The preparation method of pyrenetetraone bridged triptycene-palladium porphyrin compound comprises the steps:

[0120] (1) Synthesis of 2,6,14-trinitrotriptycene

[0121] Add 200ml of concentrated nitric acid and 5g of triptycene to a 500mL round bottom flask in turn, stir, heat to 65°C, reflux for 12-24h under stirring, add water and stir after cooling to room temperature, filter the precipitate with a Buchner funnel, and wash with water for two time, vacuum-dried to obtain a pale yellow solid; use 200-300 mesh silica gel to pass through the column, the eluent is ethyl acetate:petroleum ether=1:3, collect the product of the third band, and obtain 2,6,14-trinitro Triptycene compound 0.8g, yield 33%.

[0122] (2) Synthesis of 2,6,14-triaminotriptycene

[0123]Add 50ml of dichloride, 0.8g of 2,6,14-trinitrotriptycene, 1.65g of sodium borohydride and 0.2g of palladium / carbon (5%) to a 250ml pear-shaped bottle, and react for 1 to 2 hours under nitrogen protection , add 1...

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Abstract

The invention discloses serial compounds with triptycene as a framework and in bridge connection with metalloporphyrin through pyrene tetrone and a preparation method therefor, and belongs to the photoelectric conversion material field. The compound molecular formula is C320H348N24M3. The structural formula is shown in the specification. Triptycene is subjected to nitration by utilization of concentrated nitric acid, and 2,6,14-trinitro-triptycene; after reduction, a reaction with propionic anhydride, p-toluenesulfonic acid and potassium nitrate is carried out, then sodium hydroxide is added, hydrolysis is carried out, and 2,6,14-triamino-3,7,15-trinitro-triptycene is prepared; after reduction of stannous chloride, ethanol and concentrated hydrochloric acid, 2,3,6,7,14,15-hexaamino triptycene hexachloro hydrochloride. 3,5-bis-tert-butyl benzaldehyde and pyrrole are reacted and porphyrin is prepared; porphyrin is reacted with cupric acetate and cupric nitrate solutions and nitro copper porphyrin is prepared; 4-amino-1,2,4-triazole is added, a reaction is carried out, and an amino substituted nitro copper porphyrin is prepared; after reduction, diamino copper porphyrin is prepared. 2,3,6,7,14,15-hexaamino triptycene hexachloro hydrochloride and 2,7-bis-tert-butyl pyrene-4,5,9,10- tetrone are reacted, and a compound 1 is prepared; the compound 1 is reacted with the diamino copper porphyrin, and a compound 2 is prepared; after metal removal, a reaction with a methanol solution of corresponding metal acetate is carried out, and the compound is prepared.

Description

technical field [0001] The invention relates to a metalloporphyrin series compound with triptycene as a skeleton bridged by pyrenetetraketone and a preparation method thereof, belonging to the field of photoelectric conversion materials. Background technique [0002] Triptycene and its derivatives are a class of bridged ring compounds with a three-dimensional rigid structure. The highly anisotropic materials synthesized from the unique three-dimensional structure of triptycene and a series of conjugated derivatives have excellent photoelectric properties. In recent years, triptycene has shown attractive applications in many fields due to its unique structural characteristics and rich reactivity. Porphyrin compounds themselves have excellent photoelectric properties and thermal stability, and have strong characteristic electronic absorption spectra in the visible light region. The design and synthesis of optoelectronic functional materials and devices based on porphyrin comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 张汝波王勤思黄学斌
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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