Catalytic electron drives host-guest recognition.

ABSTRACT: Electron injection is demonstrated to trigger electrocatalytic chain reactions capable of releasing a solvent molecule and forming a redox active guest molecule. One-electron reduction of a hydroxy anthrone derivative (AQH-CH₂CN) results in the formation of an anthraquinone radical anion (AQ˙^-) and acetonitrile (CH₃CN). The resulting fragment of AQ˙^- exhibits high stability under mild reducing conditions, and it has enough reducing power to reduce the reactant of AQH-CH₂CN. Hence, subsequent electron transfer from AQ˙^- to AQH-CH₂CN yields the secondary AQ˙^- and CH₃CN, while the initial AQ˙^- is subsequently oxidized to AQ. Overall, the reactants of AQH-CH₂CN are completely converted into AQ and CH₃CN in sustainable electrocatalytic chain reactions. These electrocatalytic chain reactions are mild and sustainable, successfully achieving catalytic electron-triggered charge-transfer (CT) complex formation. Reactant AQH-CH₂CN is non-planar, making it unsuitable for CT interaction with an electron donor host compound (U_HAnt₂) bearing parallel anthracene tweezers. However, conversion of AQH-CH₂CN to planar electron acceptor AQ by the electrocatalytic chain reactions turns on CT interaction, generating a host CT complex with U_HAnt₂ (AQ ⊂ U_HAnt₂). Therefore, sustainable electrocatalytic chain reactions can control CT interactions using only a catalytic amount of electrons, ultimately affording a one-electron switch associated with catalytic electron-triggered turn-on molecular recognition.

SUBMITTER: Owatari Y 

PROVIDER: S-EPMC9093170 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature