Synthesis and Structure of [9]Cycloparaphenylene Catenane: An All-Benzene Catenane Consisting of Small Rings

Abstract

A catenane consisting of two [9]cycloparaphenylenes ([9]CPPs) has been synthesized. Density functional theory calculations suggested that [<i>n</i>]CPPs (<i>n</i> = 5, 6) are highly strained upon the formation of catenanes compared with the corresponding uncatenated CPPs, whereas [<i>n</i>]CPP catenanes (<i>n</i> ≥ 7) are not strained. The synthesis of ([9]CPP)([9]CPP)catenane was accomplished via the following route: (i) a spirosilylation, (ii) a nickel(0)-mediated macrocyclization, (iii) a desilylation, and (iv) reductive aromatization reactions. An X-ray diffraction analysis revealed a catenated structure of ([9]CPP)([9]CPP)catenane.