Abstract: | Seven new cryptands 3–9 containing two or three aromatic rings in one bridge were prepared in good yields by treating N,N'-bis(p-chlorophenol)-substituted diaza-18-crown-6 ( 2 ) with three oligoethylene glycol ditosylates, 1,3-propanediol ditosylate, 2,6-pyridinedimethanol ditosylate, α,α'-dibromo-o-xylene and α,α'-dibromo-p-xylene. Because of the convenient synthesis of 2 from N,N'-bis(methoxymethyl)diaza-18-crown-6 ( 1 ) and the relative ease of isolation of the cryptand products, this is an excellent method for the design of three-dimensional cavities containing aromatic fragments. In an attempt to better understand the synthetic route to the cryptands, the crystal structures of KI·2 and Na Picrate·2 were determined using X-ray analysis. In addition, crystal structure analyses of cryptands 3, 6 and 8 were used to establish their structures. |