A new photo-switchable "on-off" host-guest system comprising cucurbit[7]uril (CB[7]) and a photoresponsive cinnamamide derivative (trans-(3-phenyl-acryloylamino)-acetic acid, E-1) is studied. The cinnamamide derivative and CB[7] forms a stable 1 : 1 host-guest complex (CB[7]·E-1) with a high binding constant (K = 2.1 × 10(4) M(-1)). Irradiation of UV light (300 nm) to an aqueous solution of CB[7]·E-1 induces the E- to Z-conformational change of the cinnamamide derivative, which then leads to the dissociation of the complex as evidenced by UV-visible and (1)H-NMR spectroscopy. The reverse process, photo-induced host-guest complex formation between CB[7] and Z-1 is achieved by irradiation of UV light at 254 nm. The photo-switchable "on-off" host-guest system shows high reversibility and switching efficiency, which makes it potentially useful in designing photoresponsive gating systems.
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