The thermodynamically controlled reactions of water-soluble tetraformylcavitand 2 with two equivalents of H(2)N(CH(2))(n) NH(2) (n=2-4) in the presence of a suitable templating guest give hemicarceplexes 1 a-c⋅guest, the yield of which depends on the match between size and shape of the guest and that of the inner phase. These hemicarceplexes are dynamic and dissociate upon addition of acid and reform upon basification. In water, they exchange guests through temporary hydrolysis of imine bonds. To test 1 b as molecular reaction flask, 3-noradamantyldiazirine 6 was encapsulated and photolyzed at 350 nm to produce Bredt olefin protoadamantene 5 and 1-noradamantyldiazomethane 8 in a 4:1 ratio. Encapsulated protoadamantene is stable for days at room temperature in (CD(3))(2)SO/CD(3)CN (t(1/2) = 5.5 days) and has a lifetime of several minutes in D(2)O.

A moisture-triggered release system was developed using porous metal-organic materials as encapsulating agents. Release of both hydrophilic (ethyl butyrate) and hydrophobic (D-limonene) fragrance compounds was investigated by gas adsorption measurement, thermogravimetric analysis and gas chromatography-mass spectroscopy. These materials exhibit exceptional fragrance compatibility and controlled release compared to the current leading encapsulation technology.