A light-driven molecular shuttle is organized on a gold electrode surface. The assembly consists of a ferrocene-functionalized beta -cyclodextrin, Fc-beta -CD, molecule threaded on a monolayer-immobilized long alkyl component containing a photoisomerizable azobenzene unit, and terminated with a bulky anthracene group. The Fc-beta -CD resides preferentially on the trans-azobenzene component, and photoisomerization of the trans-azobenzene to the cis-azobenzene state causes the translocation of the Fc-beta -CD to the alkyl-chain component of the assembly. The state of the molecular shuttle is electronically transduced by chronoamperometry. The interfacial electron transfer rate constants for the oxidation of the ferrocene units of Fc-beta -CD in the respective positions are k(t) = 65 s(-1) and k(c) = 15 s(-1). The light-driven translocation of Fc-beta -CD is reversible, and proceeds by the cyclic isomerization of the azobenzene component between the trans and cis states.