Related Experiment Video
Updated: Jun 24, 2026
05:48
Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Polyester-graft-phosphorylcholine prepared by ring-opening polymerization and click chemistry
Beth M Cooper1, Delphine Chan-Seng, Debasis Samanta
1Department of Polymer Science and Engineering, University of Massachusetts, Amherst, MA 01003, USA.
Chemical Communications (Cambridge, England)
|March 27, 2009
Summary
Aliphatic polyesters were modified using click chemistry to attach phosphorylcholine (PC). This method enables the creation of advanced biomaterials with enhanced biocompatibility.
Area of Science:
- Polymer Chemistry
- Biomaterials Science
- Organic Synthesis
Background:
- Aliphatic polyesters are widely used in biomedical applications.
- Surface modification is crucial for improving the biocompatibility of synthetic polymers.
- Phosphorylcholine (PC) is a zwitterionic phosphoryl group found in cell membranes, known for its excellent biocompatibility and resistance to protein adsorption.
Purpose of the Study:
- To develop a facile and efficient method for the surface functionalization of aliphatic polyesters with phosphorylcholine (PC).
- To create novel biomaterials with enhanced hemocompatibility and reduced inflammatory responses.
- To explore the potential of click chemistry for precise polymer modification.
Main Methods:
- Synthesis of PC-substituted azides.
- Click chemistry reaction between azide-functionalized polyesters and PC-substituted alkynes (or vice versa).
- Characterization of the modified polyesters using techniques such as NMR, FTIR, and XPS.
Main Results:
- Successful grafting of PC moieties onto the surface of aliphatic polyesters was confirmed.
- The PC-substituted polyesters exhibited significantly reduced protein adsorption compared to unmodified polyesters.
- Enhanced hemocompatibility, including reduced platelet adhesion and hemolysis, was observed for the modified materials.
Conclusions:
- Click chemistry provides a versatile and efficient platform for the surface modification of aliphatic polyesters with phosphorylcholine.
- The resulting PC-substituted polyesters demonstrate improved biocompatibility, making them promising candidates for various biomedical applications.
- This approach offers a pathway to engineer advanced biomaterials with tailored surface properties for enhanced performance in biological environments.
Related Concept Videos
01:20Types of Step-Growth Polymers: Polyesters
The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...
01:16Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
01:20Anionic Chain-Growth Polymerization: Overview
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
00:57Cationic Chain-Growth Polymerization: Mechanism
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
01:03Step-Growth Polymerization: Overview
Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
Many natural and synthetic polymers are produced by...
01:17Ziegler–Natta Chain-Growth Polymerization: Overview
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...