Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry
| Authors | |
|---|---|
| Year of publication | 2021 |
| Type | Article in Periodical |
| Magazine / Source | POLYMER CHEMISTRY |
| MU Faculty or unit | |
| 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 |
| Attached files | |
| 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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