A cyclic oligophenylene containing two 1,8-naphthalene units bridged by two face to-face biphenyl linkages exhibiting unusual strain and π-π interaction

GRAPHICS 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.