Issue 27, 2022

Introducing SuFEx click chemistry into aliphatic polycarbonates: a novel toolbox/platform for post-modification as biomaterials

Abstract

As a biodegradable and biocompatible biomaterial, aliphatic polycarbonates (APCs) have attracted substantial attention in terms of post-polymerization modification (PPM) for functionalization. A strategy for the introduction of sulfur(VI)-fluoride exchange (SuFEx) click chemistry into APCs for PPM is proposed for the first time in this work. 4′-(Fluorosulfonyl)benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (FMC) was designed as a SuFEx clickable cyclic carbonate for APCs via ring-opening polymerization (ROP), and an operational and nontoxic synthetic route was achieved. FMC managed to undergo both ROP and PPM through the SuFEx click chemistry organocatalytically without constraining or antagonizing each other, using 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) as a co-organocatalyst here. Its ROP was systematically investigated, and density functional theory (DFT) calculations were performed to understand the acid–base catalytic mechanism in the anionic ROP. Exploratory investigations into PPM by SuFEx of poly(FMC) were conducted as biomaterials, and the one-pot strategies to achieve both ROP and SuFEx were confirmed.

Graphical abstract: Introducing SuFEx click chemistry into aliphatic polycarbonates: a novel toolbox/platform for post-modification as biomaterials

Supplementary files

Article information

Article type
Paper
Submitted
18 5 2022
Accepted
13 6 2022
First published
13 6 2022

J. Mater. Chem. B, 2022,10, 5203-5210

Introducing SuFEx click chemistry into aliphatic polycarbonates: a novel toolbox/platform for post-modification as biomaterials

W. Sun, K. Lu, L. Wang, Q. Hao, J. Liu, Y. Wang, Z. Wu and H. Chen, J. Mater. Chem. B, 2022, 10, 5203 DOI: 10.1039/D2TB01052F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements