Thermosensitive type organic/inorganic hybrid dendrimers and preparation method thereof

A dendritic and macromolecular technology, applied in the field of organic/inorganic hybrid dendritic macromolecules and their preparation, to achieve the effect of reducing the difficulty of synthesis

Inactive Publication Date: 2014-04-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although more and more POSS-based hybrid dendrimers have been prepared, so far, there are few reports on temperature-responsive POSS-based hybrid dendrimers.

Method used

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  • Thermosensitive type organic/inorganic hybrid dendrimers and preparation method thereof
  • Thermosensitive type organic/inorganic hybrid dendrimers and preparation method thereof
  • Thermosensitive type organic/inorganic hybrid dendrimers and preparation method thereof

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Effect test

Embodiment 1

[0034] The present invention relates to POSS 8 -EtG 1 Preparation and synthesis. Synthetic route reference Figure 1-3 .

[0035] 1.1 The core point is a first-generation ethoxyether dendron with pentafluorophenol active ester ( 1b ) Synthesis

[0036] A first-generation ethoxyether dendron with the core point as a carboxyl group 1a (2.30 g, 3.50 mmol, refer to literature Li, W.; Zhang, A.; Schlüter, A. D. Chem. Commun. 2008 , 5523 and Yan J T; Li W; Liu K; Wu D L; Chen F; WuP Y; Zhang A. Chem. Asian J. 2011, 6, 3260 synthesis) and pentafluorophenol (0.97 g, 5.3 mmol) dissolved in 30 mL of dry dichloromethane and at -15 o C was stirred for 10 min, then 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.81 g, 4.23 mmol) was added to the solution. The mixed solution was stirred at room temperature for 12 h, washed with saturated sodium bicarbonate solution and saturated brine, and the organic phase was dried with anhydrous magnesium sulfate and filtered. The...

Embodiment 2

[0042] The present invention relates to POSS 8 -EtG 2 Preparation and synthesis. Synthetic route reference Figure 1-3 .

[0043] 2.1 The core point is the diethoxyether branching unit of pentafluorophenol active ester ( 2b ) Synthesis

[0044] Diethoxyether dendron with the core point as carboxyl group 2a (2 g, 0.84 mmol, refer to literature Li, W.; Zhang, A.; Schlüter, A. D. Chem. Commun. 2008 , 5523 and Yan J T; Li W; Liu K; Wu D L; Chen F; WuP Y; Zhang A. Chem. Asian J. 2011, 6, 3260 synthesized) and pentafluorophenol (0.24 g, 1.30 mmol) dissolved in 20 mL of dry dichloromethane and at -15 o C was stirred for 10 min, then 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.20 g, 0.98 mmol) was added to the solution. The mixed solution was stirred at room temperature for 12 h, washed with saturated sodium bicarbonate solution and saturated brine, and the organic phase was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated ...

Embodiment 3

[0049] The synthetic route reference of the present invention Figure 9 .

[0050] Synthesis of dendrons with double bonds at the nucleus: Add 1 to 1.5 mmol of acryloyl chloride in dry dichloromethane (10 mL) dropwise to a solution of 1 mmol of benzyl alcohol at the nucleus ( 1a ) or second generation ( 2a ) ethoxyether dendrons, triethylamine (3~4.5 mmol) and DMAP (0.3~0.45 mmol) in dry DCM (100 mL) solution, keep the ice bath temperature at 0 during the dropwise addition oC After half an hour, the ice bath was removed, and stirring was continued at room temperature for 4 h, and then methanol was added dropwise to terminate the reaction. The reaction solution was sequentially washed with saturated NaHCO 3 solution and saturated NaCl solution, and after separation, use anhydrous MgSO 4 The organic phase is dried and filtered. Repurify with silica gel column chromatography, developing solvent is DCM / MeOH (30:1, v / v), obtains colorless oil ( 1b or 2b ).

[0051] Take 0....

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Abstract

The invention relates to thermosensitive type organic / inorganic hybrid dendrimers and a preparation method thereof. The hybrid dendrimers are prepared through chemical reaction between multifunctional polyhedral oligomeric silsesquioxane (POSS) with reaction activity and alcoxyl ether dendronized elements with reactive functional groups in nuclei. Compared with dendrimers of other types, the dendrimers have the beneficial effects that spherical polymers with plenty of peripheral groups can be obtained under the condition of low algebra, thus greatly reducing the synthesis difficulty of the dendrimers; meanwhile, the dendrimers endow materials with good thermosensitivity and biocompatibility; therefore, the dendrimers are expected to be applied to the fields such as drug controlled release, catalysis, intelligent materials and the like.

Description

technical field [0001] The invention relates to an organic / inorganic hybrid dendritic macromolecule and a preparation method thereof, in particular to a temperature-sensitive organic / inorganic hybrid dendritic macromolecule and a preparation method thereof. Background technique [0002] Dendritic macromolecules are a kind of dendritic three-dimensional macromolecules with a highly branched structure, which start from a multifunctional core and gradually repeat growth through dendronization units. Compared with traditional linear macromolecules, dendrimers have the following salient features: (1) Dendrimers have clear molecular weight and molecular size, regular structure, and molecular volume, shape and functional groups can be determined at the molecular level. Precise control; (2) The interior of the molecule has a wide cavity, and the surface of the molecule has a very high density of functional groups; (3) The single molecule scale is at the nanometer level. The unique ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/42C08G77/00C07F7/18C08G65/48
Inventor 张阿方苏新艳李娟夏文杰李文刘坤
Owner SHANGHAI UNIV
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