Light‐Fueled Transformations of a Dynamic Cage‐Based Molecular System

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Abstract: In a chemical equilibrium, the formation of high‐energy species—in a closed system—is inefficient due to microscopic reversibility. Here, we demonstrate how this restriction can be circumvented by coupling a dynamic equilibrium to a light‐induced E/Z isomerization of an azobenzene imine cage. The stable E‐cage resists intermolecular imine exchange reactions that would “open” it. Upon switching, the strained Z‐cage isomers undergo imine exchange spontaneously, thus opening the cage. Subsequent isomerization of the Z‐open compounds yields a high‐energy, kinetically trapped E‐open species, which cannot be efficiently obtained from the initial E‐cage, thus shifting an imine equilibrium energetically uphill in a closed system. Upon heating, the nucleophile is displaced back into solution and an opening/closing cycle is completed by regenerating the stable all‐E‐cage. Using this principle, a light‐induced cage‐to‐cage transformation is performed by the addition of a ditopic aldehyde.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Light‐Fueled Transformations of a Dynamic Cage‐Based Molecular System ; day:19 ; month:01 ; year:2023 ; extent:10
Angewandte Chemie ; (19.01.2023) (gesamt 10)

Creator: Ovalle, Marco
Kathan, Michael
Toyoda, Ryojun
Stindt, Charlotte N.
Crespi, Stefano
Feringa, Ben L.

DOI: 10.1002/ange.202214495

URN: urn:nbn:de:101:1-2023012014201733253693

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Ovalle, Marco
Kathan, Michael
Toyoda, Ryojun
Stindt, Charlotte N.
Crespi, Stefano
Feringa, Ben L.

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