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Macrocycles containing aromatic or heterocyclic units within the macrocyclic core draw an increasing attention for the last few decades.[1] The aromatic units, being rigid building blocks, allow the design and synthesis of molecular cavities with defined spatial characteristics, and also serve as binding sites for hosts capable of interacting with their π-electron systems.[1b-d] On the other side heterocyclic rings are also of special interest for the construction of cyclophane-type molecules[2] because the presence of donor heteroatoms provides means for the incorporation of a binding site for transition metals within the macrocyclic structure. Macrocycles formed both by the aromatic and the heterocyclic units with three-coordinated phosphorus atoms as donors[3] are able to provide a variety of the donoracceptor and the non-valent interactions so they are of interest both for supramolecular chemistry (in particular as selective sensors[4]) and as unusual ligands for transition metal catalyzed reactions in organic synthesis,[5] as the geometry and well-defined position of the complexing donor centers could lead to specific catalytically active complexes.[6] However, the chemistry of cyclophane ligands containing phosphine groups as donor centers within the macrocyclic skeleton is less developed than that of their oxygen or nitrogen analogues.[3] This fact has been mainly attributed to the air sensitivity of these compounds and the poor yields obtained in their preparations by high-dilution[3,7] or template methods,[3] although the high-yield synthesis of a few types of phosphamacrocycles has been reported. [3,8] To the best of our knowledge there are no examples of P-containg cyclophanes with chiral intramolecular cavity. But we are sure that if P-containing cyclophanes, especially chiral, with a unique shape, distinct architecture, and set of functional groups become easily available from natural or synthetic sources, they would start to inspire the imagination of supramolecular chemists to devise and synthesize novel sophisticated receptors, machines, and devices,[1-3,6,8] as well as new types of molecular reactors.[9] Recently, a highly effective self-assembly process giving macrocyclic tetraphosphines with a relatively large hydrophobic prismatic or helical twisted cavities by condensation of the three-component system diamine/ formaldehyde/phosphine was discovered.[10] In the present work diamines possessing inherent chirality, namely N-alkyl-2,6-diamino-9,10-dihydro-9,10-ethanoanthracenecis-11,12-dicarboximide 2-4,[11] were used as spatially divided diamine component of the self-assembling system to prepare a novel type of P,N-containing cyclophanes with chiral intramolecular cavity.

Novel P,N-Containing Cyclophane with a Chiral Hydrophobic Cavity