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Quinacridone derivatives containing urea bonds and gels thereof

A technology of quinacridone and derivatives is applied in the field of quinacridone derivative luminescent materials and the gel formed thereof, and can solve rare problems and the like

Active Publication Date: 2010-06-23
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Molecular gels can respond to changes in the external environment, including light, heat, enzymes, magnetism, redox, and ions, but there are very few reports on ultrasound-responsive gels. Therefore, in order to effectively design functions with superior assembly performance Molecules must develop a deep understanding of their gelation mechanism

Method used

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  • Quinacridone derivatives containing urea bonds and gels thereof
  • Quinacridone derivatives containing urea bonds and gels thereof
  • Quinacridone derivatives containing urea bonds and gels thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of compound DUC6

[0025] Under nitrogen protection conditions, DCB6 (2.55 g), sodium iodide (0.5 g) and phthalimide potassium salt (2.96 g) in dimethylformamide solution (100 ml) were heated at 60 ° C for 24 hours, cooled , 200 ml of water was added to stop the reaction, and the resulting solid was subjected to column chromatography (silica gel, chloroform) to obtain 2.70 g (88%) of the orange DUP6 target product.

[0026] DUP6 (0.90 g) and hydrazine hydrate (5.0 ml) were refluxed in 90 ml of tetrahydrofuran / ethanol=1:1 (volume / volume) for 5 hours, the organic solvent was evaporated under reduced pressure, and 100 ml of water was added for suction filtration to obtain the filter cake to dry. The solid was recrystallized from chloroform and cyclohexane to obtain the target product DUN6 (0.54 g, 90%).

[0027] DUN6 (0.4 g) was added to a solution of 50 ml of hexyl isocyanate (0.24 g) in 30 ml of chloroform / methanol=1:1 (volume / volume), and s...

Embodiment 2

[0028] Embodiment 2: the synthesis of compound DUC8

[0029] The synthesis of compound DUC8 is the same as in Example 1, except that 1,8-dibromooctane is used instead of 1,6-dibromohexane when preparing DCBn. Product DUC8 mass spectrum molecular ion peak: 820.8. Elemental analysis according to chemical formula C 50 h 72 N 6 o 4 Calculated: C: 73.13%; H: 8.84%; N: 10.23%; O: 7.79%. Experimental values: C: 73.28%; H: 8.79%; N: 10.02%.

Embodiment 3

[0030] Embodiment 3: the synthesis of compound DUC10

[0031] The synthesis of compound DUC10 is the same as in Example 1, except that 1,10-dibromodecane is used instead of 1,6-dibromohexane when preparing DCBn. Product DUC10 mass spectrum molecular ion peak: 877.2. Elemental analysis according to chemical formula C 54 h 80 N 6 o 4 Calculated: C: 73.93%; H: 9.19%; N: 9.58%; O: 7.30%. Experimental values: C: 73.69%; H: 9.35%; N: 9.40%.

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Abstract

The invention belongs to the technical field of organic photoelectric material and particularly relates to four quinacridone derivative luminescent materials containing urea bond functional groups and gels thereof. The structural formula of the luminescent material is shown as follows, wherein n is 6, 8, 10 or 12, and the luminescent material is obtained through the following steps: DCBn reacts with potassium phthalimidate in DMF to obtain DUPn, a pure product is obtained through simple column chromatography, a protection group is separated in solution with hydrazine hydrate as alkaline environment to form end amino, and the product directly reacts with cyanate. The luminescent material can obtain stable gel in the organic solvent and reflects stronger yellow green fluorescence emission.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to four quinacridone derivative light-emitting materials containing urea bond functional groups and the gel formed therefrom. Background technique [0002] In recent years, it has been found that certain small molecular organic compound solutions can gel organic solvents at very low concentrations (even lower than 1 wt%) to form organic gels, or molecular gels. Such organic compounds are called gelling factors. Gelation factor can spontaneously aggregate and assemble into an ordered structure in a solvent, and then gel the whole system. The preparation method is that the gel factor is heated and dissolved in an organic solvent, and then cooled to room temperature. A three-dimensional network system is formed between molecules through hydrogen bonding, van der Waals forces, hydrophobic interactions, and π-π interactions. Among them, stimuli-resp...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06
Inventor 王悦
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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