Building with cubane-1,4-diyl. Synthesis of aryl-substituted cubanes, p-[n]cubyls, and cubane-separated bis(arenes)

On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-di yl, a highly reactive species, shown here to be a versatile precursor to nu merous aryl substituted cubanes, available now for the first time in high y ield. The diyl is demonstrated to provide a good route to bicubyl and its d erivatives. A kind of "living polymerization" of the diyl is developed to g ive the p-[n]cubyls. These oligomers are rigid rods made up of cubanes link ed together at the 1 and 4 positions, each cubane adding similar to 4.15 An gstrom to the length. The properties of these rods, some more than 15 Angst rom long, are discussed, as are methods for modifying their solubility. X-r ay crystallographic analyses of some of these compounds an presented, with emphasis on packing parameters.