Poly(2-oxazoline) with Pendant Hydroxyl Groups via a Silyl Ether-Based Protecting Group. Kim, J., Beyer, V., & Becer, C. R. MACROMOLECULES, November, 2022. doi abstract bibtex The introduction of a functionality onto a poly(2-oxazoline) (POx) chain has been widely explored, yet reports of POx bearing hydroxyl side chains in a well-defined manner have not. Here, we report a simple yet elegant approach for the synthesis of POx with pendant hydroxyl groups through use of silyl protecting groups. First, a hydroxyl group containing 2-oxazoline monomer was synthesized from L-caprolactone, which on its own results in poorly defined polymers. Moreover, protecting the hydroxy group with silyl ether-based protecting group led to well-defined polymers with free hydroxyl groups on the side chains upon deprotection. Finally, copolymers with 2-ethyl-2-oxazoline resulted in polymers with tunable hydrophilicity, and copolymers with 2-n-propyl-2-oxazoline resulted in polymers with tunable thermoresponsive behavior in water.
@article{kim_poly2-oxazoline_2022,
title = {Poly(2-oxazoline) with {Pendant} {Hydroxyl} {Groups} via a {Silyl} {Ether}-{Based} {Protecting} {Group}},
issn = {0024-9297},
doi = {10.1021/acs.macromol.2c02050},
abstract = {The introduction of a functionality onto a poly(2-oxazoline) (POx) chain has been widely explored, yet reports of POx bearing hydroxyl side chains in a well-defined manner have not. Here, we report a simple yet elegant approach for the synthesis of POx with pendant hydroxyl groups through use of silyl protecting groups. First, a hydroxyl group containing 2-oxazoline monomer was synthesized from L-caprolactone, which on its own results in poorly defined polymers. Moreover, protecting the hydroxy group with silyl ether-based protecting group led to well-defined polymers with free hydroxyl groups on the side chains upon deprotection. Finally, copolymers with 2-ethyl-2-oxazoline resulted in polymers with tunable hydrophilicity, and copolymers with 2-n-propyl-2-oxazoline resulted in polymers with tunable thermoresponsive behavior in water.},
urldate = {2022-12-14},
journal = {MACROMOLECULES},
author = {Kim, Jungyeon and Beyer, Valentin and Becer, C. Remzi},
month = nov,
year = {2022},
}
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