Abstract

Capped cyclodextrins are prepared by reaction with a planar porphine molecule capable of hydrogen bonding to hydroxyl groups of the torus-shaped cyclodextrin. Absorption, fluorescence and NMR data indicated the formation of a semi-closed assembly where the porphine molecule “caps” the cyclodextrin, closing off one end of the cyclodextrin host. A quantitative change in the absorption profile of an assembly prepared from highly water-soluble 2-hydroxypropyl-β-CD and planar 4, 4′4″,4‴-(21H, 23H-porphine-5,10,15, 20-tetrayl)tetrakis benzoic acid (POR) occurred highly selectively in response to a guest-host complexation of pentachlorophenol.

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