A Cyclic Oligophenylene Containing Two 1,8-Naphthalene Units Bridged by Two Face-to-Face Biphenyl Linkages Exhibiting Unusual Strain and π−π Interaction

Abstract

1,8-[1,8-Naphthalenediylbis(4',4-biphenyldiyl)]naphthalene, a very stable strained cyclophane, has been synthesized in moderate yield using the copper-catalyzed coupling of 1, 8-bis(4-(tributylstannyl)phenyl)naphthalene. The X-ray analysis of the titled compound discloses bent p,p'-biphenylylene chains with splayed naphthalene rings, and the p,p'-biphenylylene chains located face-to-face indicate a fairly strong pi-pi interaction.