A Vinyl Ether-Functional Polycarbonate as a Template for Multiple Postpolymerization Modifications

Title
A Vinyl Ether-Functional Polycarbonate as a Template for Multiple Postpolymerization Modifications
Authors
조상호Gyu Seong HeoSarosh KhanJessica HuangDavid A. HunstadMahmoud ElsabahyKaren L. Wooley
Issue Date
2018-05
Publisher
Macromolecules
Citation
VOL 51, NO 9-3242
Abstract
A highly reactive vinyl ether-functionalized aliphatic polycarbonate and its block copolymer were developed as templates for multiple postpolymerization conjugation chemistries. The vinyl ether-functional sixmembered cyclic carbonate monomer was synthesized by a well-established two-step procedure starting from 2,2-bis-(hydroxymethyl)propionic acid. An organobase-catalyzed ring-opening polymerization of the synthesized monomer afforded polycarbonates with pendant vinyl ether functionalities (PMVEC). The vinyl ether moieties on the resulting polymers were readily conjugated with hydroxyl- or thiolcontaining compounds via three different postpolymerization modification chemistries: acetalization, thio-acetalization, and thiol− ene reaction. Acetal-functionalized polycarbonates were studied in depth to exploit their acid-labile acetal functionalities. Acetalization of the amphiphilic diblock copolymer of poly(ethylene glycol) methyl ether (mPEG) and PMVEC, mPEG113-b-PMVEC13, with the model hydroxyl compound 4-methylbenzyl alcohol resulted in a maximum of 42% acetal and 58% hydroxyl side chain groups. Nonetheless, the amphiphilicity of the block polymer allowed for its self-assembly in water to afford nanostructures, as characterized via dynamic light scattering and transmission electron microscopy. The kinetics of acetal cleavage within the block polymer micelles were examined in acidic buffered solutions (pH 4 and 5). In addition, mPEG-b-PMVEC and its hydrolyzed polymer mPEG-b-PMHEC (i.e., after full cleavage of acetals) exhibited minimal cytotoxicity to RAW 264.7 mouse macrophages, indicating that this polymer system represents a biologically nonhazardous material with pH-responsive activity.
URI
http://pubs.kist.re.kr/handle/201004/67588
ISSN
0024-9297
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KIST Publication > Article
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