Issue 47, 2021

Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry

Abstract

We report the design of easily accessible, photocleavable meso-methyl BODIPY monomers suitably functionalised for incorporation into macromolecules. Firstly a BODIPY-diol as a novel AA-type bifunctional monomer is reported. Secondly, from the same common BODIPY precursor, a clickable, azide functionalised AB-type hetero-bifunctional monomer was prepared. Photochemical studies of model compounds confirmed the ability of these compounds to undergo photocleavage in green light (λ > 500 nm). Their usefulness for photoclippable macromolecular systems is then demonstrated: firstly by incorporating the diols into polyurethane hydrogels shown to undergo photocleavage and hence dissolution under visible light irradiation and secondly, the preparation of water-soluble macromolecular photocages able to photorelease small molecules. Thus the results presented herein describe a proof-of-principle for BODIPY-based photoresponsive materials, for example, for use as degradable polymers, sacrificial materials for lithography or for the delivery of caged pharmaceuticals.

Graphical abstract: Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry

Supplementary files

Article information

Article type
Paper
Submitted
15 9 2021
Accepted
15 11 2021
First published
16 11 2021
This article is Open Access
Creative Commons BY license

Polym. Chem., 2021,12, 6927-6936

Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry

P. Strasser, M. Russo, P. Stadler, P. Breiteneder, G. Redhammer, M. Himmelsbach, O. Brüggemann, U. Monkowius, P. Klán and I. Teasdale, Polym. Chem., 2021, 12, 6927 DOI: 10.1039/D1PY01245B

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