In host–guest chemistry, a carcerand (from Latin carcer 'prison') is a host molecule that completely entraps its guest (which can be an ion, atom or other chemical species) so that it will not escape even at high temperatures.[1] This type of molecule was first described in 1985 by Donald J. Cram and coworkers. The complexes formed by a carcerand with permanently imprisoned guests are called carceplexes.
In contrast, hemicarcerands allow guests to enter and exit the cavity at high temperatures but will form stable complexes at ambient temperatures.[2] The complexes formed by a hemicarcerand and a guest are called hemicarceplexes.