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Compound with intramolecule change transfer and its preparing process

A compound and molecular technology, applied in the field of compounds with intramolecular charge transfer and their preparation

Inactive Publication Date: 2004-08-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metal phthalocyanines assembled from alkoxy groups and substituted tetrathiafulvalene monomers have not been reported.

Method used

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  • Compound with intramolecule change transfer and its preparing process
  • Compound with intramolecule change transfer and its preparing process
  • Compound with intramolecule change transfer and its preparing process

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0022] The preparation method of compound described in the present invention is described further below:

[0023] (1) 2-(4,5-Di-n-hexylthio-1,3-dithio-2-ylidene)-5-hydroxymethylene-5-hydrogen-6-dihydro-1,3-dithio Preparation of [4,5-b][1,4]dithiocyclohexane:

[0024] After dissolving zinc salt (Zincate) in acetone, add hexyl bromide dissolved in acetone dropwise in the boiling state, wherein the molar ratio of zinc salt (Zincate) to hexyl bromide is 1:5.3, continue to reflux for 2-4 hours, and filter with suction Remove insolubles. The solvent was distilled off, and the residue was purified by column chromatography to obtain 4,5-di-n-hexylthio-1,3-dithiol-2-thione, one of the raw materials required for the coupling reaction. The reaction formula is as follows: Show:

[0025]

[0026] After reflux for 20 hours in the same way, another raw material 5,6-dihydro-5-acetoxymethylene-1,3-dithio[4,5-b][1,4] was purified to obtain the coupling reaction Dithiocyclohexane-2-thione...

Embodiment

[0040] 4,5-Di-n-hexylthio-1,3-dithiole-2-thione

[0041] 8g zinc salt (Zincate) (11.2mmol) was dissolved in 100mL acetone, heated to reflux with stirring, 50mL acetone solution containing 9.4mL (60mmol) bromohexane was added dropwise, and refluxed for 4 hours. Suction filtration to remove insoluble matter. Acetone was removed by rotary evaporation. The residue was subjected to column chromatography (chloroform:petroleum ether=1:2 as the developing solvent) and the developing solvent was rotated to obtain 8 g of orange-red oil with a yield of 98%.

[0042] MS(EI): m / z(%)=367(M + +1, 14.119), 366 (M + , 27.196)

[0043] 5,6-Dihydro-5-acetoxymethylene-1,3-dithio[4,5-b][1,4]dithiocyclohexane-2-thione

[0044] Add 7.2g (10mmol) Zincate and 100mL acetone into a 250mL three-neck flask. 11.4 mL (80 mmol) 2,3-dibromopropyl acetate / 50 mL acetone were added dropwise under stirring and reflux, and the reaction was carried out for about 20 hours. TLC tracking, the developing solvent...

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PUM

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Abstract

The present invention discloses the structure and preparing process of a molecular assembly of metal phthalocyamine and substituted dithioethylene tetrathiofulvalene. The said molecular assembly is a macro-molecular compound with intramolecule charge transfer, and can be used in molecule switch field.

Description

technical field [0001] The invention relates to a molecular assembly of metal phthalocyanine and substituted disulfideethylenetetrathiafulvalene and a preparation method thereof. Background technique [0002] Tetrathiafulvalene (TTF) and its derivatives are good π-electron donors (Donor), which can generate stable cationic radicals. This free radical can generate conductive intermolecular charge transfer complexes with numerous electron acceptors, for example, the CT-complex of tetrathiofulvalene and tetracyanoquinodimethane (TTF-TCNQ ) have metallic conductivity at room temperature. At the same time, tetrathiafulvalene and its derivatives are good molecular assembly materials, which can be matched with other functional material molecules to form intramolecular CT-complexes. This intramolecular charge transfer complex has multiple electrical, optical, and magnetic activities, and can be used as a molecular electronic device material for VLSI or as a "molecular switch" for ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00
Inventor 沈永嘉胡莹玉许煦
Owner EAST CHINA UNIV OF SCI & TECH
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