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The effect of pendant group structure on the thermoresponsive properties of N-substituted polyesters

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Abstract

Synthetic polymers exhibiting reversible lower critical solution temperature (LCST), such as poly(N-isopropylacrylamide) (PNIPAM), are intriguing materials with various potential applications. We recently developed a new class of biodegradable thermoresponsive polyesters (TR-PEs) based on N-substituted diol monomers. TR-PEs exhibited reversible cloud point temperatures (Tcp) between 0–50 °C and were shown to be non-cytotoxic. The synthesis of N-substituted diols and TR-PEs is highly modular, allowing for a wide variety of possible homo- and copolyesters. In this work, we report the synthesis and characterization of 20 homopolyesters in order to better understand the structure–property relationship of TR-PEs. UV-vis spectroscopy showed that the Tcp of TR-PEs was highly dependent on pendant group structure, such as secondary or tertiary amides, cyclic and linear groups, and substitution of oxygen atoms. Structure-Tcp analysis provides a correlation between Tcp and the number of heteroatoms relative to the number of carbon atoms in the pendant group thereby providing a rationale for the design of thermoresponsive polyesters with desired Tcp values. To demonstrate the expanded tunability of the TR-PE system, copolyesters bearing covalently attached ibuprofen were synthesized and shown to exhibit LCST behavior dependent on comonomer hydrophilicity.

Graphical abstract: The effect of pendant group structure on the thermoresponsive properties of N-substituted polyesters

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Publication details

The article was received on 18 Aug 2017, accepted on 02 Nov 2017 and first published on 03 Nov 2017


Article type: Paper
DOI: 10.1039/C7PY01391D
Citation: Polym. Chem., 2017, Advance Article
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    The effect of pendant group structure on the thermoresponsive properties of N-substituted polyesters

    J. P. Swanson, M. A. Cruz, L. R. Monteleone, M. R. Martinez, P. J. Costanzo and A. Joy, Polym. Chem., 2017, Advance Article , DOI: 10.1039/C7PY01391D

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