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

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Authors

STRASSER Paul RUSSO Marina STADLER Pauline BREITENEDER Patrick REDHAMMER Guenther HIMMELSBACH Markus BRUGGEMANN Oliver MONKOWIUS Uwe KLÁN Petr TEASDALE Ian

Year of publication 2021
Type Article in Periodical
Magazine / Source POLYMER CHEMISTRY
MU Faculty or unit

Faculty of Science

Citation
Web https://pubs.rsc.org/en/content/articlelanding/2021/PY/D1PY01245B
Doi http://dx.doi.org/10.1039/d1py01245b
Keywords PHOTOREMOVABLE PROTECTING GROUPS; PHOTOPROTECTING GROUPS; POLYMER; DERIVATIVES; REACTIVITY; COPOLYMER; MICELLES; RELEASE
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Description 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 (lambda > 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.
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