This project aims to develop rotaxane-based artificial molecular machines capable of controlled light-induced transmembrane transport of sugars. The central hypothesis is that integrating photoresponsive switching and ring shuttling with dynamic covalent bond formation is expected to enable directional, stimulus-controlled transport of cargo across lipid bilayers. The proposed rotaxanes will contain axles featuring multiple stations and macrocycles incorporating phenylboronic acid (PBA) moieties capable of covalently binding diols. When embedded within the liposome membrane, the PBA-functionalised macrocycle will capture saccharide substrates at the membrane exterior. Subsequent azobenzene photoisomerisation will induce steric destabilisation of the primary station, triggering macrocycle shuttling towards the station at the membrane interior. If the liposome internal microenvironment has a lower pH, PBA-diol affinity will be reduced, resulting in substrate release and completion of the light-driven transport cycle. The efficiency and directionality of such systems are governed by the interplay of individual (photo)chemical reactions within a complex reaction network describing the transport cycle.