Abstract
A series of quaternary ammonium cyclophanes, 2b∼e and 4a∼d, having well-defined hydrophobic cavities rationally designed with diphenylmethane and naphthylphenylmethane units, respectively, were synthesized and fully characterized. A systematic study on the molecular recognition and discrimination properties of these hosts in neutral water was carried out. Whereas host 2 having diphenylmethane units formed inclusion complexes selectively with aromatic guests, host 4 having naphthylphenylmethane units were proved to form inclusion complexes with bulky aliphatic guests that were not complexed by host 2.