By a non-conjugating trimethylene chain, a π-extended p-phenylenediamine unit and a trinitrofluorenone unit are connected to furnish an electron-donor–acceptor dyad, which prefers a π–π stacking geometry between donor and acceptor units exhibiting a charge-transfer band in the visible-near infrared region. Redox-triggered structural switching is induced upon one-electron oxidation or reduction with a change in conformation into a non-stacking extended form. The dyad with a lipoate subunit, which is suitable for the formation of a self-assembled monolayer, can serve as a promising material to make a molecular electronic junction working as a current rectifier.
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