Issue 40, 2023

Water-soluble polyphosphonate-based bottlebrush copolymers via aqueous ring-opening metathesis polymerization

Abstract

Ring-opening metathesis polymerization (ROMP) is a versatile method for synthesizing complex macromolecules from various functional monomers. In this work, we report the synthesis of water-soluble and degradable bottlebrush polymers, based on polyphosphoesters (PPEs) via ROMP. First, PPE-macromonomers were synthesized via organocatalytic anionic ring-opening polymerization of 2-ethyl-2-oxo-1,3,2-dioxaphospholane using N-(hydroxyethyl)-cis-5-norbornene-exo-2,3-dicarboximide as the initiator and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the catalyst. The resulting norbornene-based macromonomers had degrees of polymerization (DPn) ranging from 25 to 243 and narrow molar mass dispersity (Đ ≤ 1.10). Subsequently, these macromonomers were used in ROMP with the Grubbs 3rd-generation bispyridyl complex (Ru-G3) to produce a library of well-defined bottlebrush polymers. The ROMP was carried out either in dioxane or in aqueous conditions, resulting in well-defined and water-soluble bottlebrush PPEs. Furthermore, a two-step protocol was employed to synthesize double hydrophilic diblock bottlebrush copolymers via ROMP in water at neutral pH-values. This general protocol enabled the direct combination of PPEs with ROMP to synthesize well-defined bottlebrush polymers and block copolymers in water. Degradation of the PPE side chains was proven resulting in low molar mass degradation products only. The biocompatible and biodegradable nature of PPEs makes this pathway promising for designing novel biomedical drug carriers or viscosity modifiers, as well as many other potential applications.

Graphical abstract: Water-soluble polyphosphonate-based bottlebrush copolymers via aqueous ring-opening metathesis polymerization

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Mai 2023
Accepted
26 Sep 2023
First published
26 Sep 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 11273-11282

Water-soluble polyphosphonate-based bottlebrush copolymers via aqueous ring-opening metathesis polymerization

D. A. Resendiz-Lara, S. Azhdari, H. Gojzewski, A. H. Gröschel and F. R. Wurm, Chem. Sci., 2023, 14, 11273 DOI: 10.1039/D3SC02649C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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