The synthesis of rigid receptors based on triphenylene ketals, including some improved procedures, is described in detail. Since chemical transformations are strongly influenced by the rigid character and steric bulkiness of the receptors, the construction of a subunit allowing quicker synthetic development is also reported. The preparation of these receptor structures involves an oxidative trimerization and a subsequent repeated isomerization procedure. The scope for the attachment of sterically demanding affinity groups on the receptor scaffold and the corresponding subunit is discussed, and the molecular structures and available space for molecular recognition of the chirally modified systems are outlined by some crystal structures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

Multiply iodinated biaryls can be prepared in yields up to 75% by direct oxidative coupling reaction of the iodinated arenes. The PIFA-mediated dehydrodimerization is superior to all other known methods. The developed protocol is reliable and easy to perform.

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A modification of our triphenylene ketal based receptor facilitates electrospray tandem mass spectrometry investigations. Binding affinities of eleven potential substrates, e.g. caffeine and other xanthine alkaloids, are probed in the gas phase with collision induced dissociation. The relative stabilities of the substrate-receptor complexes are rapidly determined and the findings are correlated with the corresponding results in solution.