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We studied charge transport phenomena through a core substitutednaphthalenediimide (NDI) single-molecule junctions using the electrochemicalSTM-based break junction technique in combination with DFT calculations. Theconductance switch among three well-defined states is acquired byelectrochemically controlling the redox state of the pendent diimide unit ofthe molecule in ionic liquid, and the conductance difference is more than oneorder of magnitude between di-anion states and neutral state. The potentialdependent charge transport characteristics of the NDI molecules are confirmedby DFT calculations accounting for electrochemical double-layer effects on theconductance of the NDI junctions. This work suggests that the integration ofredox unit in the pendent position with strong coupling to molecular backbonecan significantly tune the charge transport of the single-molecule device bycontrolling different redox states.

A Three State NDI Switch: Integration of Pendant Redox Unit for Conductance Tuning