TY - JOUR
T1 - Poly(2-oxazoline) with Pendant Hydroxyl Groups via a Silyl Ether-Based Protecting Group
AU - Kim, Jungyeon
AU - Beyer, Valentin
AU - Becer, C.R.
N1 - Copyright © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 (https://creativecommons.org/licenses/by/4.0/).
PY - 2022/11/28
Y1 - 2022/11/28
N2 - 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 ε-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.
AB - 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 ε-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.
UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-85143497416&partnerID=MN8TOARS
UR - https://pubs.acs.org/doi/10.1021/acs.macromol.2c02050
U2 - 10.1021/acs.macromol.2c02050
DO - 10.1021/acs.macromol.2c02050
M3 - Article
SN - 0024-9297
VL - 55
JO - Macromolecules
JF - Macromolecules
IS - 23
ER -