Our expedition in eight-membered ring compounds: from planar dehydrocyclooctenes to tub-shaped chiral tetraphenylenes.

Our research focus for almost forty years concerning eight-membered ring compounds is herein summarized. The design and preparation of these structurally unique compounds featuring a central cyclooctene ring are described in the context of their planar or tub-shaped conformations. Furthermore, their intrinsic properties and potential applications are also presented.