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At the present time different molecular devices, created on the basis of organic supramolecular host-guest complexes, are becoming increasingly popular. In this paper the photocontrolled molecular system, consisting of crown-containing 2-styryl dyes as guest molecules, as well as 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and cucurbit[7]uril (CB[7]) as host molecules, is advanced. The aim of the research was to study the processes of self-assembly and breakage of this molecular ensemble, taking place under the action of UV irradiation.