Light-driven progesterone release from trans-1 in a biphasic solvent system. CD3CN and cyclopentane formed two distinct immiscible solvent layers. Slice-selective 1H NMR(42) indicated that the complex of progesterone inside trans-1 dissolved only in CD3CN. Ultraviolet irradiation triggered cage disassembly and concomitant progesterone release. Slice-selective 1H NMR revealed that the released progesterone distributed across both solvent phases.