Method for preparing self-healed phosphorescence organic gel material

An organic gel, self-healing technology, applied in the direction of luminescent materials, chemical instruments and methods, etc.

Inactive Publication Date: 2019-12-20
CHANGCHUN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the preparation and properties of self-healing phosphorescent materials that have broader application prospects in optical sensing, biomarkers, etc.

Method used

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  • Method for preparing self-healed phosphorescence organic gel material
  • Method for preparing self-healed phosphorescence organic gel material
  • Method for preparing self-healed phosphorescence organic gel material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of diimine ligand Ura-Phen-1 in structural formula (I)

[0024]

[0025] Under nitrogen protection, 4-(4-bromobutoxy)benzaldehyde (1.028g, 4mmol), uracil (0.672g, 6mmol) and anhydrous potassium carbonate (0.828g, 6mmol) were successively added to 30mL N, In N-dimethylformamide, the reaction was continued for 36 hours after slowly heating to 80°C. After the temperature dropped to room temperature, 150 mL of deionized water was added to the reaction system. Stir at room temperature until the solution is clear and then filter. The collected crude product is purified by column chromatography using ethyl acetate / petroleum ether (v / v=2 / 1) as eluent to obtain 0.644 g of white Ura-CHO-1 solid (56% yield). Ura-CHO-1 (0.576 g, 2 mmol), 1,10-phenanthroline-5,6-dione (0.420 g, 2 mmol) and ammonium acetate (1.540 g, 20 mmol) were added to 15 mL of glacial acetic acid, The reaction was continued for 6 hours after heating to 118° C. under the protecti...

Embodiment 2

[0026] Embodiment 2: the synthesis of diimine ligand Ura-Phen-2 in structural formula (I)

[0027]

[0028] The synthesis method of Ura-Phen-2 is similar to that of Ura-Phen-1, replacing 4-(4-bromobutoxy)benzaldehyde (1.028g, 4mmol) with 4-(6-bromohexyloxy)benzaldehyde (1.140 g, 4 mmol)), and 0.732 g of white Ura-CHO-2 solid powder was obtained (58% yield). Then Ura-CHO-2 (0.101 g, 2 mmol), 1,10-phenanthroline-5,6-dione (0.420 g, 2 mmol) and ammonium acetate (1.540 g, 20 mmol) were added to 15 mL of glacial acetic acid, Heated to 118°C under nitrogen protection and continued to react for 6 hours. After the temperature dropped to room temperature, 150 mL of deionized water was added to the reaction system, and the pH of the reaction system was adjusted to about 7 with 10% aqueous sodium hydroxide solution. The precipitated solid was recrystallized from methanol to collect 0.138 g of pale yellow Ura-Phen-2 solid powder (81% yield). 1 H NMR (DMSO, 400Hz, ppm): δ = 1.350 (t,...

Embodiment 3

[0029] Embodiment 3: the synthesis of diimine ligand Ura-Phen-3 in structural formula (I)

[0030]

[0031] The synthesis method of CHO-Ura-3 is similar to that of CHO-Ura-1, replacing 4-(4-bromobutoxy)benzaldehyde (1.028g, 4mmol) with 4-(8-bromooctyloxy)benzaldehyde (1.252g, 4mmol), 0.728g of white CHO-Ura-3 solid powder was obtained, the yield was 53%. CHO-Ura-3 (0.688g, 2mmol), 1,10-phenanthroline-5,6-dione (0.420g, 2mmol) and ammonium acetate (1.540g, 20mmol) were added to 15mL of glacial acetic acid, in Heated to 118°C under nitrogen protection and continued to react for 6 hours. After the temperature dropped to room temperature, 150 mL of deionized water was added to the reaction system, and the pH of the reaction system was adjusted to about 7 with 10% aqueous sodium hydroxide solution. After the precipitated solid was recrystallized from methanol, 0.982 g of light yellow Ura-Phen-3 solid powder was collected (89% yield). 1 H NMR (DMSO, 400Hz, ppm): δ = 1.276 (d, ...

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Abstract

The invention provides an experiment method for preparing a self-healed phosphorescence organic gel through a physical doping process. The microstructure of the prepared self-healed phosphorescence organic gel is shown in formula (I) in the description. The invention designs and synthesizes a uracil functionalized Re(I) complex, in addition, an organic gel which is capable of emitting characteristic phosphorescence spectrum of the Re(I) complex can be prepared together with polyacrylic acid through physical doping, the gel is capable of enduring stress of 0.191MPa and strain of 525%, and in addition, a sample which is broken down by pull can be recovered to 40% of an initial state within 5 minutes.

Description

technical field [0001] The invention belongs to the preparation of a self-healing phosphorescent organic gel material, which provides a new research idea for further expanding the application field of phosphorescent materials and designing new phosphorescent materials. Background technique [0002] Since the scientific concept of "supramolecular chemistry" was put forward in 1988, supramolecular chemistry has developed rapidly, using intermolecular non-covalent bond interaction (such as hydrogen bond interaction, electrostatic interaction, intermolecular multiple interaction, etc.) A large number of self-healing gel materials with self-healing properties have been prepared through the interaction of valence bonds (such as borate ester bonds, acylhydrazone bonds, etc.). In particular, the development and application of self-healing luminescent gel materials has gradually become a new research hotspot in recent years. Through research, it is found that factors such as the con...

Claims

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Application Information

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IPC IPC(8): C09K11/02C09K11/06
CPCC09K11/025C09K11/06C09K2211/1074C09K2211/188
Inventor 司振君魏青云鲍文丽左青卉王志杰李翔王钟俭
Owner CHANGCHUN UNIV OF SCI & TECH
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