[6.6](1,8)Naphthalenophane containing 2,2′-bithienyl-5,5′-ylene bridges

Two isomeric 1,8-[1,8-naphthylenebis(2,2′-bithienyl-5,5′-ylene)]naphthalenes (major and minor isomers) were synthesized using the coupling reaction of 1,8-di(5-lithio-2-thienyl)naphthalene with CuCl2. The major isomer easily isomerized photochemically to yield the minor isomer. The redox and fluorescence behavior of the two isomers reflect both face-to-face interaction of the 2,2′-bithienyl-5,5′-ylene units and deformation of the naphthalene moieties.