A series of novel oligobipyridine molecules linked by pseudo-crown-ethers have been synthesized and have been shown to be excellent host molecules for small cationic quests. The ion pair complexes that result follow the expected “same-fit” concept for the ether pocket size of the host and the ionic radii of the guest. When the peripheral bipyridine units are metallated, these flexible complexes contain the ability to function as electro- or photo-activated mechanical switches in a variety of solvents directed by the alkali ion encapsulation. The ‘on' or ‘off' position of the molecular switch is visibly or electrochemically detected through the photoelectric or electrochemical response of two facially interacting square planar transition metals. The reversible nature of this process serves as the basis for these systems to perform as molecular switching devices capable of functioning as analytical sensors, energy transfer and storage devices, and ion transport shuttles for semi-permeable membranes. The ion transport properties were probed using a liquid-liquid (aqueous-organic) membrane.