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Furyl-terminated hyperbranched polyester as well as preparation method and application thereof

A technology of hyperbranched polyester and furanyl group is applied in the field of terminal furanyl hyperbranched polyester and its preparation, and can solve the problems of reducing the heat resistance of hyperbranched polymers, hindering the application of fluorescent properties, lacking biocompatibility and the like, Achieve the effects of high reproducibility of the preparation method, easy industrialized mass production, and low cost

Active Publication Date: 2022-04-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are no rigid groups introduced into the hyperbranched polymer chains synthesized by the above two techniques. Although the terminal amino or hydroxyl groups keep the reactivity of the polymer, they also greatly reduce the heat resistance of this type of hyperbranched polymer. , in addition, the lack of a molecular structure with good biocompatibility in the synthesized hyperbranched polymer hampers the application of its fluorescent properties in biomedical imaging

Method used

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  • Furyl-terminated hyperbranched polyester as well as preparation method and application thereof
  • Furyl-terminated hyperbranched polyester as well as preparation method and application thereof
  • Furyl-terminated hyperbranched polyester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] This embodiment provides a furyl-terminated hyperbranched polyester whose algebra is 1, and its structural formula is as follows:

[0045]

[0046] Among them, R 1 It is the nucleus of the furyl-terminated hyperbranched polyester, containing 1 carboxyl group and 1 acid anhydride; R 2 It is a branch of the furyl-terminated hyperbranched polyester, containing one hydroxyl group and three carboxyl groups; n is 9. Its preparation method comprises the following steps:

[0047] S1. Carboxyl-terminated hyperbranched polyester

[0048] Add 0.04mol of trimellitic anhydride, 0.12mol of citric acid, 0.31g of p-toluenesulfonic acid, 100mL of toluene and 100mL of dioxane into a reaction vessel equipped with a reflux device, a nitrogen protection device and a mechanical stirring device, and first stir at 100°C for 6h , and then reacted at 125°C for 5 hours to obtain a carboxyl-terminated hyperbranched polyester;

[0049] S2. Epoxy terminated hyperbranched polyester

[0050] A...

Embodiment 2

[0054] This embodiment provides a furan-terminated hyperbranched polyester whose generation number is 2, and its structural formula is as follows:

[0055]

[0056] Among them, R 1 It is the nucleus of the furyl-terminated hyperbranched polyester, containing 1 carboxyl group and 1 acid anhydride; R 2 It is a branch of the furyl-terminated hyperbranched polyester, containing one hydroxyl group and three carboxyl groups; n is 27. The difference between its preparation method and Example 1 is that the raw materials in step S1 are 0.04mol trimellitic anhydride, 0.48mol citric acid, 1g p-toluenesulfonic acid, 100mL toluene and 100mL dioxane; the amount of epichlorohydrin used in step S2 The amount of sodium hydroxide is 1.6 mol, and the amount of sodium hydroxide is 42.3 g; the amount of 2-furanmethylamine in step S3 is 0.162 mol.

Embodiment 3

[0058] This embodiment provides a furan-terminated hyperbranched polymer whose generation number is 3, and its structural formula is as follows:

[0059]

[0060] Among them, R 1 It is the nucleus of the furyl-terminated hyperbranched polyester, containing 1 carboxyl group and 1 acid anhydride; R 2 It is a branch of the furyl-terminated hyperbranched polyester, containing one hydroxyl group and three carboxyl groups; n is 81. The difference between its preparation method and Example 1 is that the raw materials in step S1 are 0.04mol trimellitic anhydride, 1.56mol citric acid, 3.07g p-toluenesulfonic acid, 100mL toluene and 100mL dioxane; in step S2, epichlorohydrin The dosage is 4.85 mol, and the dosage of sodium hydroxide is 41.7 g; the dosage of 2-furylmethylamine in step S3 is 0.486 mol.

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Abstract

The invention discloses furyl-terminated hyperbranched polyester as well as a preparation method and application thereof. The structure of the furyl-terminated hyperbranched polyester disclosed by the invention is shown as a formula (I), and the furyl-terminated hyperbranched polyester has a non-traditional luminous fluorescence response characteristic due to the fact that a molecular skeleton of the furyl-terminated hyperbranched polyester contains a large amount of hydroxyl, secondary amine and other reactive hydrogen-containing groups and ester groups; the hyperbranched polyester has better thermal stability, biocompatibility and the like due to the fact that a large number of rigid furan structures are contained at the tail end, the hyperbranched polyester can further react with maleimide and other dienes to form a self-repairing functional polymer with reversible covalent DA bonds, and therefore the reaction activity of the hyperbranched polyester is kept; the material is suitable for the fields of biological fluorescence imaging, medical drug sustained release, biosensing, light emitting diodes and the like, and is mainly prepared from bio-based raw materials, so that the cost is low, and the preparation method is high in reproducibility and easy for industrial mass production.

Description

technical field [0001] The invention belongs to the field of polymer luminescent materials, and relates to a furyl-terminated hyperbranched polyester and a preparation method and application thereof. Background technique [0002] In recent years, organic light-emitting materials have attracted the interest of many researchers due to their special photophysical properties and their applications in biological monitoring, cell imaging, and drug delivery. Traditional fluorescent polymers are generally doped or grafted with light-emitting molecules on the polymer matrix. These light-emitting molecules usually have structures such as large Π delocalized conjugated unsaturated groups, benzene rings or heterocycles, or organic-inorganic light-emitting molecules. Direct doping of crystals, these substances can produce strong fluorescence effects when combined with polymers, and are widely used in the fields of fluorescence, biosensing and light-emitting diodes, but due to the large p...

Claims

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Application Information

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IPC IPC(8): C08G63/02C08G63/91C08G83/00
CPCC08G63/02C08G63/91C08G83/005C08G83/006
Inventor 阮文红黄思琦章明秋
Owner SUN YAT SEN UNIV