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Cage type polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide as well as preparation method and application of polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide

A polyisonitrile and hybrid technology is applied in the field of cage-type polysilsesquioxane-based star-shaped hybrid helical polyisonitrile and its preparation, which can solve the problems of rare hybrid star-shaped polyisonitrile research and the like, and achieves The experimental conditions are not demanding, the preparation is simple, and the operation is convenient.

Active Publication Date: 2020-11-27
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past few decades, various functional polyisonitriles have been reported one after another. However, most of these polyisonitriles are linear, but there are few studies on hybrid star polyisonitriles.

Method used

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  • Cage type polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide as well as preparation method and application of polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide
  • Cage type polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide as well as preparation method and application of polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide
  • Cage type polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide as well as preparation method and application of polysilsesquioxane-based star-shaped hybrid spiral polyisocyanide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation method of organic / inorganic hybrid palladium catalyst

[0042] a. Dissolve 0.17mmol (0.20g) of octaamino POSS and 4.09mmol (0.63g) of monopropynyl succinate into 50mL of dichloromethane, and add 2.73mmol (1.03g) of O-benzotriazepam Azole-tetramethyluronium hexafluorophosphate, 2.73 mmol (0.37 g) of 1-hydroxybenzotriazole and 10 mL of triethylamine. Under nitrogen atmosphere, react at room temperature for 24h, stop the reaction. The organic phase was taken with 30 mL of dichloromethane, washed three times with saturated ammonium chloride solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution successively, dried by adding anhydrous sodium sulfate, and evaporated to remove the solvent to obtain a crude product. Add 2 mL of dichloromethane and precipitate with 20 mL of ether to obtain intermediate I; the structural formula is as follows:

[0043] In the formula

[0044] b. Add 2mmol (726.64mg) of bis(trie...

Embodiment 2

[0049] Example 2: Initiating Chiral C 10 Isonitrile Polymerization

[0050] Chiral C 10Isonitrile polymerization is carried out under anhydrous and oxygen-free conditions, and 1.60 mg (0.0003 mmol) of the palladium catalyst prepared in Example 1 is added in a 10 mL polymerization bottle, and the chiral C 10 Isonitrile isonitrile monomer 19.31mg (0.0614mmol), vacuumize and inflate with nitrogen for 3 times, add 1mL dry tetrahydrofuran, reflux reaction at 55°C for 8h, add 10mL methanol to quench, precipitate the polymer, wash with methanol Centrifuge 5 times to obtain a yellow flocculent precipitate, and vacuum-dry until the mass remains unchanged.

[0051] The structural formula of the phenylisonitrile monomer in the present embodiment is:

[0052]

[0053] The structural formula of the product obtained is:

[0054]

Embodiment 3

[0055] Example 3: Chiral C 10 Isonitrile block three-armed hydrophilic isonitrile

[0056] Add 15.2mg of the polymer prepared in Example 2 and 139.81mg (0.19mmol) of the three-armed hydrophilic isonitrile monomer into a 10mL polymerization bottle, vacuumize and inflate with nitrogen three times, add 0.8mL of dry tetrahydrofuran, and reflux at 55°C After 20 hours, 10 mL of methanol was added to quench the polymer, and the polymer was washed 5 times with methanol, centrifuged to obtain a white flocculent precipitate, and vacuum-dried until the mass remained unchanged.

[0057] The structural formula of the phenylisonitrile monomer in the present embodiment is:

[0058]

[0059] The structural formula of the product obtained is:

[0060]

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Abstract

The invention discloses cage type polysilsesquioxane(POSS)-based star-shaped hybrid spiral polyisocyanide as well as a preparation method and an application thereof. The structure of the POSS-based star-shaped hybrid spiral polyisocyanide is shown as the following general formula: in the formula, during preparation, firstly, aminated POSS is synthesized, then alkynyl is introduced through an amidation reaction, an organic / inorganic hybrid palladium catalyst is obtained through reaction with palladium, then isocyanide polymerization is initiated, and POSS-based star-shaped hybrid spiral polyisocyanide is prepared. According to the invention, an organic material and an inorganic material are combined, so that the prepared catalyst has good catalytic capability, and the star-shaped hybrid spiral polyisocyanide can be easily and conveniently obtained. The polymer obtained by the catalyst is of an eight-arm star-shaped spiral structure, and has high molecular weight and narrower molecular weight distribution. The product has great potential application value in the fields of self-assembly, drug loading, chiral separation, dye adsorption and the like.

Description

technical field [0001] The invention belongs to the field of polymer catalysis and preparation of functional polymers, in particular to a cage-type polysilsesquioxane (POSS)-based star-shaped hybrid helical polyisonitrile and its preparation method and application. Background technique [0002] Polyisonitrile is a synthetic polymer with stable helical conformation that can be used in many aspects such as chiral recognition, enantiomer separation and asymmetric catalysis. Because of its readily available monomers and simple polymerization methods, it is very popular. In the past few decades, various functional polyisonitriles have been reported one after another. However, most of these polyisonitriles are linear, but there are few studies on hybrid star polyisonitriles. Compared with linear polymers, star polymers have a smaller dynamic mechanical size in solution, and have the characteristics of low solution and bulk viscosity, which is of great significance for the process...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08G77/398C08G77/38
CPCC08G61/12C08G77/398C08G77/38C08G77/045C08G2261/11C08G2261/126C08G2261/1426C08G2261/1432C08G2261/148C08G2261/74
Inventor 邹辉李前炜吴启亮
Owner HEFEI UNIV OF TECH
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