Multi-State Redox and Light-Driven Switching of Pseudorotaxanation and Cation Shuttling

Robert Hein*, Yohan Gisbert, Ben L. Feringa*

*Corresponding author voor dit werk

OnderzoeksoutputAcademicpeer review

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Samenvatting

The modulation of molecular recognition underpins numerous wide-ranging applications and has inspired the development of a myriad of switchable receptors, in particular photo- or redox-responsive hosts. Herein, we report a highly versatile three-state cation receptor family and switch system based on an overcrowded alkene strapped with crown ethers, which can be switched by both redox and light stimuli, thereby combining the advantages of both approaches. Specifically, the neutral switches can be quantitatively converted between anti- and syn-folded receptor geometries by irradiation, leading to the discovery of a significant increase or decrease in cation binding affinity, which was exploited to shuttle the pseudorotaxane-forming dibenzylammonium guest between the switchable crown ethers of slightly different sizes. Alternatively, two-electron oxidation to the orthogonal, dicationic, nonvolatile state completely turns off cation binding to the host, thereby ejecting the guest. Upon reduction, the metastable syn-folded state is first formed, which then thermally relaxes, resulting in a unique, autonomous, and cation-dependent multistate switching cascade.

Originele taal-2English
Artikelnummer5c00997
Pagina's (van-tot)13649–13657
Aantal pagina's9
TijdschriftJournal of the American Chemical Society
Volume147
Nummer van het tijdschrift16
Vroegere onlinedatum11-apr.-2025
DOI's
StatusPublished - 23-apr.-2025

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