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

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 1H NMR studies show high photostability and photoconversion yields. Where the photoaddressable (E)- an...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (15), p.11328-11334
Main Authors: Villarón, David, Bos, Jasper E., Kohl, Fabien, Mommer, Stefan, de Jong, Jorn, Wezenberg, Sander J.
Format: Article
Language:English
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Summary: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 1H NMR studies show high photostability and photoconversion yields. Where the photoaddressable (E)- and (Z)-isomers exhibit comparable binding affinities, as determined by 1H 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01018