text: In host–guest chemistry the bistable states of molecular switches differ in their affinity for guests. Many early examples of such systems are based on crown ether chemistry. The first switchable host is described in 1978 by Desvergne & Bouas-Laurent who create a crown ether via photochemical  anthracene dimerization. Although not strictly speaking switchable the compound is able to take up cations after a photochemical trigger and exposure to acetonitrile gives back the open form.
  In 1980 Yamashita et al. construct a crown ether already incorporating the anthracene units (an anthracenophane) and also study ion uptake vs photochemistry.
  Also in 1980 Shinkai throws out the anthracene unit as photoantenna in favor of an azobenzene moiety and for the first time envisions the existence of molecules with an on-off switch. In this molecule light triggers a trans-cis isomerization of the azo group which results in ring expansion. Thus in the trans form the crown binds preferentially to ammonium, lithium and sodium ions while in the cis form the preference is for potassium and rubidium (both larger ions in same alkali metal group). In the dark the reverse isomerization takes place.
  Shinkai employs this devices in actual ion transport mimicking the biochemical action of monensin and nigericin: in a biphasic system ions are taken up triggered by light in one phase and deposited in the other phase in absence of light.