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Preparation method of double-sensitivity cyclodextrin supermolecule aggregate

A supramolecular aggregate and sensitive technology, applied in the field of functional materials, can solve the problem of no photosensitive stimuli-responsive supramolecular polymer, and achieve the effect of good photosensitivity and temperature sensitivity, and broad application prospects.

Inactive Publication Date: 2014-01-22
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although there are many research reports on stimuli-responsive CD supramolecular assemblies, there is no research on photosensitive cinnamic acid groups combined with CD to prepare stimuli-responsive supramolecular polymers.

Method used

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  • Preparation method of double-sensitivity cyclodextrin supermolecule aggregate
  • Preparation method of double-sensitivity cyclodextrin supermolecule aggregate
  • Preparation method of double-sensitivity cyclodextrin supermolecule aggregate

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Experimental program
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Effect test

Embodiment 1

[0024] The synthesis of embodiment 1,4-acetyl cinnamic acid

[0025] Add 4.60g (28mmol) of 4HCA and 10mL of anhydrous pyridine into a 100mL three-necked flask, install a constant temperature heating system and a stirring system, stir for 30min under a constant temperature ice bath at 0°C, then add 7.5mL of acetic anhydride at this temperature, and continue stirring After stirring for 1.5 hours, the obtained solution was heated to reflux for 5 hours under constant temperature oil bath magnetic stirring at 130°C, and the obtained solution was poured into a 500mL beaker, washed twice with 0.1mol / L hydrochloric acid solution, and filtered to obtain a white powder with a large amount of deionized water. washing. Take the filter cake and dry it under vacuum at 50°C for 24 hours to obtain cinnamic acid derivative 4ACA with acetylated hydroxy group as white powder.

Embodiment 2

[0026] The synthesis of embodiment 2,4-acetyl cinnamoyl chloride

[0027] Add 4.12g (20mmol) of 4-acetyl cinnamic acid and 20mL of thionyl chloride into a 100mL one-necked flask, then add 0.018g of DMF as a catalyst, and 10mL of dichloromethane as a solvent. ℃ under a constant temperature oil bath with magnetic stirring and heated to reflux for 7 hours, and distilled off under reduced pressure to remove the solvent and unreacted thionyl chloride. The product obtained was a pale yellow powder.

Embodiment 3、4

[0028] The preparation of embodiment 3,4HCA-CD

[0029] Add 5g (4.4mmol) of β-CD and 150mL of anhydrous pyridine into a 250mL three-neck flask, stir in a constant temperature ice bath at 0°C until β-CD is completely dissolved, and dissolve 0.7633g (3.4mmol) of 4-acetyl cinnamic acid Prepare a solution in 14 mL of anhydrous pyridine, add this solution dropwise into a three-necked flask within 20 minutes, and continue to stir and react at room temperature for 5 hours after the dropwise addition is completed. After the reaction was completed, a little water was added to terminate the reaction, and pyridine was distilled off under reduced pressure. The residue was extracted with methanol, and then recrystallized twice from methanol-water to obtain 4HCA-CD. The product obtained was a reddish-brown powder.

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Abstract

The invention discloses a preparation method of a double-sensitivity cyclodextrin supermolecule aggregate, belonging to the technical field of functional materials. The preparation method comprises the following steps of preparing a host molecule-photosensitive 4-hydroxycinnamic acid-cyclodextrin (4HCA-CD) by using 4-hydroxycinnamic acid (4HCA) to modify beta-cyclodextrin (beta-CD); using trithioester with adamantine (AD) at tail end as a chain transfer agent, and preparing temperature-sensitive object polymer-double-arm adamantine-poly(N-isopropyl acrylamide)-adamantine (AD-PNIPAM-AD) by using a reversible addition-fragmentation chain transfer free radical polymerization (RAFT) method; constructing a double-sensitivity supermolecule inclusion complex 4HCA-CD / AD-PNIPAM-AD by utilizing comprehensive performance of a beta-CD dewatering cavity and AD; and self-assembling the 4HCA-CD / AD-PNIPAM-AD to form the supermolecule aggregate which is capable of realizing reversible conversion in shape and size by changing light and temperature. The supermolecule aggregate prepared by the preparation method disclosed by the invention has good light / temperature double sensitivities and is capable of carrying out smart response onto external stimulus, so that the supermolecule aggregate has a wide application prospect in the fields of drug loading, controlled release, and the like.

Description

technical field [0001] The invention discloses a method for preparing a double-sensitive cyclodextrin supramolecular aggregate, which belongs to the technical field of functional materials. Background technique [0002] Cyclodextrins (Cyclodextrins, CDs) are cyclic oligosaccharides composed of D-glucopyranose units linked by α-1,4-glycosidic bonds. much attention. The CD molecule has a slightly conical hollow cylindrical three-dimensional ring structure. In its structure, the outer side is composed of secondary hydroxyl groups of C2 and C3 and primary hydroxyl groups of C6, which is hydrophilic; The shielding effect forms the hydrophobic region. The characteristics of the inner cavity of CD and the outer hydrophilic make CD and its derivatives can be included with hydrophobic molecules of matching size according to van der Waals force, hydrophobic interaction force, interaction between host and guest molecules, etc., to prepare cyclodextrin compounds , cyclodextrin nanopa...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08B37/16C08F120/54C08F2/38
Inventor 施冬健刘蓉瑾陈明清吴超陈元勋潘阳阳
Owner JIANGNAN UNIV
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