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Method for synthesizing fluorescent functional polyester-based amphiphilic polymer

A functional molecule, polyester-based technology, applied in the field of synthesizing fluorescent functional polyester-based amphiphilic polymers, can solve the problems of difficult polymer end group and topology regulation, poor biocompatibility, uncontrollable polymerization, etc. Excellent biodegradability, easy stability, low price effect

Pending Publication Date: 2021-08-24
ANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many methods for synthesizing fluorescent functionalized amphiphilic polymer materials, including micellar polymerization, atom transfer radical polymerization, reversible addition-fragmentation chain transfer polymerization and ring-opening polymerization, etc. Many, it is difficult to precisely control the polymer terminal group and topological structure, and most of them are slow or difficult to degrade in vivo, have poor biocompatibility, and are even prone to toxicity (Progress in polymer science, 2010, 35(1- 2), 45-93. Progress in Polymer Science, 2007, 32(3), 283-351. Biomacromolecules, 2010, 11(5), 1331-1338.)

Method used

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  • Method for synthesizing fluorescent functional polyester-based amphiphilic polymer
  • Method for synthesizing fluorescent functional polyester-based amphiphilic polymer
  • Method for synthesizing fluorescent functional polyester-based amphiphilic polymer

Examples

Experimental program
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Effect test

Embodiment 1

[0042] In a nitrogen-filled glove box, add NBD-OH as an initiator in a dry polymerization reaction tube, and then add monohydroxy functionalized 7-nitrobenzo-2-oxa-1,3-oxadiazole (NBD-OH) (13.9mg, 0.05mmol), allyl glycidyl ether (0.593mL, 0.005mol), phthalic anhydride (sublimed twice) (0.74g, 0.005mol), triethylboron (TEB) / THF solution (20μL, 0.02mmol), phosphazene base (t-BuP 1 ) (5 μL, 0.02 mmol) and THF (2 mL). After feeding, shake evenly to dissolve the monomer, initiator and catalyst completely under stirring. Take it out and place it in an oil bath at 80°C under magnetic stirring for 18 hours. After the reaction, take a small amount of crude product for NMR test to calculate the monomer conversion rate. Subsequently, the crude product was precipitated three times in a mixed solvent of diethyl ether and n-hexane to obtain a purified product, which was placed in a vacuum drying oven to dry to obtain an alternating polyester with a conversion rate of phthalic anhydride mo...

Embodiment 2

[0045] The polymerization conditions are the same as in Example 1, the difference is that hydroxyrhodamine (Rh-OH) is used as the initiator, the other feeding ratios are the same, the acid anhydride is sublimated twice, reacted in an oil bath at 80°C for 18 hours, and the conversion rate of phthalic anhydride monomer 90%, the resulting polyester yield was 64%. The SEC weight average molecular weight of the obtained polymer was 5.8k Da, and the molecular weight distribution was 1.45.

Embodiment 3

[0047] The polymerization conditions were the same as in Example 1, except that 9-anthracene acetic acid was used as the initiator, the other feeding ratios were the same, the acid anhydride was sublimated twice, and the reaction was carried out in an oil bath at 80°C for 18 hours. The conversion rate of phthalic anhydride monomer was 96%, and the obtained The polyester yield was 67%. The SEC weight average molecular weight of the obtained polymer was 6.4k Da, and the molecular weight distribution was 2.23.

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Abstract

The invention discloses a method for synthesizing polyunsaturated side group-containing polyester and preparing a fluorescent functional amphiphilic polymer through post-modification of the polyunsaturated side group-containing polyester. Fluorescent functional small organic molecules such as rhodamine and the like are used as initiators, an organoboron compound is used as lewis acid and organic alkali to form different lewis acid-base pair catalytic systems, ring-opening copolymerization of cyclic anhydride and epoxide is catalyzed, and polyunsaturated side group-containing completely alternating polyesters with different molecular weights are prepared. Post-modification is conducted on unsaturated double bonds of side groups through a mercapto-alkene click reaction, and hydrophilic side groups or side chains are introduced, so as to prepare the fluorescent functional amphiphilic polymer. The catalyst is cheap and easy to obtain, the initiator is selected according to the requirement of fluorescence characteristics, different types of amphiphilic polymers can be obtained by adjusting the types of cyclic anhydride, epoxide and hydrophilic side groups, no metal is introduced in the preparation process, the main chain structure of the product is polyester, and the advantages of low toxicity, biodegradability and excellent biocompatibility are achieved.

Description

technical field [0001] The invention belongs to the technical field of functional polymer synthesis, and relates to a method for synthesizing fluorescent functional polyester-based amphiphilic polymers. Background technique [0002] Fluorescence-functionalized amphiphilic polymer materials are currently the most important drug nano-preparation carrier materials, because of their wide variety, adjustable structure, and due to their excellent fluorescence and fluorescence response characteristics, they are widely used in the field of fluorescent tracer and biosensing of drug carriers. Great value. [0003] There are many methods for synthesizing fluorescent functionalized amphiphilic polymer materials, including micellar polymerization, atom transfer radical polymerization, reversible addition-fragmentation chain transfer polymerization and ring-opening polymerization, etc. Many, it is difficult to precisely control the polymer terminal group and topological structure, and mo...

Claims

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Application Information

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IPC IPC(8): C08G63/685C08G63/58C08G63/87C08G63/84C08G63/91C09K11/06
CPCC08G63/6858C08G63/58C08G63/87C08G63/84C08G63/918C09K11/06
Inventor 王利军王芳宋海香王艳飞杨立国
Owner ANYANG INST OF TECH
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