Photoswitchable Bis(amidopyrroles): Modulating Anion Transport Activity Independent of Binding Affinity

David Villarón, Jasper E. Bos, Fabien Kohl, Stefan Mommer, Jorn de Jong, Sander J. Wezenberg

The Journal of Organic Chemistry · 2023 · 23 citations · 37 references

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Abstract

High Resolution Image Download MS PowerPoint Slide Toward photocontrol of anion transport across the bilayer membrane, stiff-stilbene, which has dimethyl substituents in the five-membered rings, is functionalized with amidopyrrole units. UV–vis and 1 H NMR studies show high photostability and photoconversion yields. Where the photoaddressable ( E )- and ( Z )-isomers exhibit comparable binding affinities, as determined by 1 H NMR titrations, fluorescence-based transport assays reveal significantly higher transport activity for the ( Z )-isomers. Changing the binding affinity is thus not a necessity for modulating transport. Additionally, transport can be triggered in situ by light.

References

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