Synthetic hosts for neutral molecules and metal ion guests

A series of lariat ether ester and amide derivatives were prepared as hosts for metal ion guests and a series of monotopic tetraaza cyclophanes was synthesized as potential molecular receptors for aromatic guests.

The lariat ether esters have either a hydrogen or propyl group geminal to the ester-containing side arm. The lariat ether amide possess geminal propyl, isopropyl and neopentyl groups. These lariat ether amides were prepared for use as ionophores in solvent polymeric membrane ion-selective electrodes.

A new method for cleavage of tosylamide protecting groups was developed which allowed monotopic tetraaza cyclophanes with alkyl spacers of varying lengths between the two polyaromatic units of the macrocycle to be prepared. A tetraaza cyclophane with eight phenylene groups in the structure was also synthesized.