There is growing interest in artifi cial receptors that serve as sensors of charged species. Studies of the interaction between hosts and organic cations can also advance our understanding of the recognition properties of biological systems. Because many bioactive molecules such as the neurotransmitters acetylcholine, serotonin, nicotine, or protonated γ -aminobutyric acid are ammonium ions, the complexation of these organic cations is of particular interest. Aliphatic biogenic amines are being monitored in several foodstuffs like fi sh, meat cheese and wine during ageing and storage. 1 The design of selectively bound host -guest complexes is a challenge for supramolecular chemistry. This chapter deals with host -guest systems including cyclophanes, calixarenes, homocalixarenes, and cucurbiturils as hosts. Such molecular containers (cavitands) should provide a cavity surrounded by rigid walls that enables close proximity of the guest to the wall of the host. In order to take advantage of cation -π interactions, aromatic subunits are necessary. The infl uences of shape, rigidity, and the chemical structure of the host molecules as well as the nature of the organic cations will be reviewed. More complex systems such as sensors and switchable host -guest complexes are applications which will play a pronounced role in the development of new receptors developed from base structures of the hosts.
Molecular Encapsulation: Organic Reactions in Constrained SystemsEdited by Udo H. Brinker and Jean-Luc Mieusset