1,4-Oxazepan-7-one trifluoroacetate: a modular monomer precursor for the synthesis of functional and biodegradable poly(amino esters)

Abstract

N-acylated poly(amino esters) (PAEs) synthesized via organocatalytic ring-opening polymerization (ROP) offer potential for tailored, functional and degradable polymers. In this study, a universal monomer precursor toward N-acylated-1,4-oxazepan-7-ones (OxP)s was synthesized using a three-step approach, allowing for the introduction of various functional groups. Two novel oxidation sensitive OxP monomers bearing a double bond and a sulfide group were designed, as well as two monomers with alkyl moieties. The organocatalytic ROP of the OxP monomers using 1,8-diazabicyclo[5.4.0]undec-7-en (DBU) and 1 (3,5 bis(trifluoromethyl)phenyl)-3-cyclohexyl thiourea (TU) as catalysts was investigated. Polymerizations were performed under ambient temperature, affording homopolymers with narrow dispersities (Đ = 1.09–1.13). As a proof of concept, a post-polymerization thiol-ene functionalization of the allyl functional PAE was performed via photo-rheology experiments. Finally, the (bio)degradability of the N acylated poly(amino esters) was evaluated through a series of degradation studies under mild enzymatic catalysis, in neutral phosphate-buffered saline solution and under accelerated conditions.

Supplementary files

Article information

Article type
Paper
Submitted
27 May 2025
Accepted
21 Jun 2025
First published
03 Jul 2025
This article is Open Access
Creative Commons BY license

Polym. Chem., 2025, Accepted Manuscript

1,4-Oxazepan-7-one trifluoroacetate: a modular monomer precursor for the synthesis of functional and biodegradable poly(amino esters)

T. Mackiol, C. Pascouau, M. Nagel, T. Bizmark, L. Montesel, J. Fischer-Schuch and P. Besenius, Polym. Chem., 2025, Accepted Manuscript , DOI: 10.1039/D5PY00522A

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