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Tuning of the morphology and sizeof supramolecular self-assembliesis of theoretical and practical significance. To date, supramoleculardriving forces in different solvents remain unclear. In this study,we first synthesized an amphiphilic β-cyclodextrin (β-CD)dimer that consists of one hydrophobic ibuprofen (Ibu) and two hydrophilicβ-CD moieties (i.e., Ibu-CD2). Ibu-CD2possesses double supramolecular driving forces, namely, the host–guestrecognition and hydrophilic–hydrophobic interaction. The host–guestinteraction of Ibu-CD2induced the formation of branchedsupramolecular polymers (SPs) in pure water, whereas the hydrophilic–hydrophobicinteraction generated spherical or irregular micelles in water/organicmixtures. The SP size increased with the increase in Ibu-CD2concentration in pure water. By contrast, the size of micelles decreasedwith the increase in volume ratio of water in mixtures. [ABSTRACT FROM AUTHOR]