2, 9-Diaza-1, 10-dioxo [10] paracyclophanes were prepared in short steps from the terephthaloyl chlorides via the corresponding 4, 6-diyne derivatives, and the amide groups on the bridge endow the skeleton with the guest-binding properties as demonstrated by complexation with adrenaline by hydrogen bonds. The chiral auxiliaries on the bridge induce diastereomeric preference in terms of the planar chirality for the octadehydro ...