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Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole

A technology of aggregation-induced luminescence and polytriazole, which is applied in chemical instruments and methods, luminescent materials, fluorescence/phosphorescence, etc., can solve the problem of less hyperbranched polymers, achieve enhanced fluorescence intensity, excellent aggregation-induced luminescence performance, and performance Improved effect

Inactive Publication Date: 2011-08-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole
  • Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole
  • Hyperbranched polytriazole with aggregation induced light-emitting performance and preparation method and application of hyperbranched polytriazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Synthesis of a first monomer with three azide groups with an alkyl chain length of 6 (m=6) and a second monomer with two triple bond groups containing tetraphenylethylene AIE active unit body.

[0050] The first monomer can be prepared according to the following specific steps:

[0051] 1,6-Dibromohexane (16.104g, 66mmol), K 2 CO 3 (20.732g, 150mmol) was added to a 250mL two-necked round bottom flask and dissolved with 60mL of acetone. The raw material 1,1,1-tris(4-hydroxyphenyl)ethane (6.128 g, 20 mmol) was dissolved in 40 mL of acetone, and was slowly added dropwise to the reaction system under reflux. After the reflux reaction for 24 hours, it was filtered, and the crude product obtained after the filtrate was spin-dried was separated by silica gel column chromatography (petroleum ether was the eluent) to obtain the first intermediate (7.941 g, yield 49.9%) as a white solid.

[0052] mp 55℃. 1 H NMR(400MHz, CDCl 3 ), δ(TMS, ppm): 6.96(d, 6H), 6.75(d, 6H), 3.91(t, 6H),...

Embodiment 2

[0068] (1) The synthesis of the first monomer and the second monomer is the same as in Example 1.

[0069] (2) The main process of the polymerization reaction is the same as in Example 1, except that the amount of the first monomer added in the reaction is 109.1 mg (0.167 mmol), and the second monomer is 95.1 mg (0.25 mmol). Obtained 204.2 mg (yield 100%) of a novel hyperbranched polytriazole with AIE performance, a yellow solid, and partly soluble. The weight average molecular weight of the dissolved part is 8500, and the molecular weight distribution is 2.91.

[0070] (3) The AIE performance of the hyperbranched polytriazole obtained in this example is the same as that of Example 1. The hyperbranched polytriazole has almost no fluorescence in its good solvent such as tetrahydrofuran solution. With the continuous addition of poor solvents such as water, the polymer Aggregation occurs, and its fluorescence intensity continues to increase, showing typical aggregation-induced lumine...

Embodiment 3

[0072] (1) The synthesis of the first monomer and the second monomer is the same as in Example 1.

[0073] (2) The main process of the polymerization reaction is the same as in Example 1, except that the amount of the first monomer added in the reaction is 22.7 mg (0.033 mmol) and the second monomer is 19.0 mg (0.05 mmol). A new type hyperbranched polytriazole with AIE performance was obtained, 25.5 mg (yield 61.2%), yellow solid. The weight average molecular weight is 4100 and the molecular weight distribution is 1.67.

[0074] (3) The AIE performance of the hyperbranched polytriazole obtained in this example is the same as that of Example 1. The hyperbranched polytriazole has almost no fluorescence in its good solvent such as tetrahydrofuran solution. With the continuous addition of poor solvents such as water, the polymer Aggregation occurs, and its fluorescence intensity continues to increase, showing typical aggregation-induced luminescence properties.

[0075] (4) The detecti...

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Abstract

The invention discloses hyperbranched polytriazole with the aggregation induced light-emitting performance and a preparation method and application of the hyperbranched polytriazole. The hyperbranched polytriazole has the following structural formula, wherein in the formula, m is in the range of 1 to 12. The hyperbranched polytriazole almost does not emit fluorescence in a good solvent. The fluorescence is strengthened when the hyperbranched polytriazole is in an aggregation state. The hyperbranched polytriazole has typical aggregation induced light-emitting performance expressively. Moreover, in the aggregation state, the polytriazole can be used for detecting multi-nitro explosives.

Description

Technical field [0001] The invention relates to a hyperbranched polytriazole with aggregation-induced luminescence performance and a preparation method and application thereof. Background technique [0002] High-efficiency solid-state luminescent materials have extremely important practical value in a variety of applications such as light-emitting diodes, solid-state lasers and fluorescent probes. However, the fluorescence quenching of traditional fluorescent chromophores in the solid state is the so-called aggregate fluorescence quenching (ACQ). This bottleneck restricts the further development of such materials. [0003] In 2001, Professor Tang Benzhong et al. reported (article number: Chem.Commun.2001, 1740) a photophysical phenomenon completely different from ACQ—aggregation-induced emission (AIE) effect: one type has Propeller-shaped molecules do not emit fluorescence in the solution state, but the fluorescence intensity of the material in the aggregate state increases, and t...

Claims

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Application Information

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IPC IPC(8): C08G73/08C09K11/06G01N21/64
Inventor 汪剑秦安军孙景志唐本忠梅菊
Owner ZHEJIANG UNIV
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