Issue 9, 2022

A disulfide-based linker for thiol–norbornene conjugation: formation and cleavage of hydrogels by the use of light

Abstract

Photolabile groups are the key components of photo-responsive polymers, dynamically tunable materials with multiple applications in materials and life sciences. They usually consist of a chromophore and a labile bond and are inherently light sensitive. An exception are disulfides, simple reversible linkages, which become photocleavable upon addition of a photoinitiator. Despite their practical features, disulfides are rarely utilized due to their impractical formation. Here, we report a disulfide-based linker series bearing norbornene terminals for facile crosslinking of thiol-functionalized macromers via light-triggered thiol–ene conjugation (TEC). Besides finding a highly reactive lead compound, we also identify an unexpected TEC-retardation, strongly dependent on the molecular linker structure and affecting hydrogel stability. Finally, we present a useful method for localized disulfide cleavage by two-photon irradiation permitting micropatterning of disulfide-crosslinked networks.

Graphical abstract: A disulfide-based linker for thiol–norbornene conjugation: formation and cleavage of hydrogels by the use of light

Supplementary files

Article information

Article type
Paper
Submitted
07 jul 2021
Accepted
03 jan 2022
First published
10 jan 2022
This article is Open Access
Creative Commons BY license

Polym. Chem., 2022,13, 1158-1168

A disulfide-based linker for thiol–norbornene conjugation: formation and cleavage of hydrogels by the use of light

M. Lunzer, B. Maryasin, T. Zandrini, S. Baudis, A. Ovsianikov and R. Liska, Polym. Chem., 2022, 13, 1158 DOI: 10.1039/D1PY00914A

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