P. Eaton, K. Pramod, T. Emrick
Apr 20, 1999
Citations
1
Influential Citations
47
Citations
Journal
Journal of the American Chemical Society
Abstract
On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of “living polymerization” of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up of cubanes linked together at the 1 and 4 positions, each cubane adding ∼4.15 A to the length. The properties of these rods, some more than 15 A long, are discussed, as are methods for modifying their solubility. X-ray crystallographic analyses of some of these compounds are presented, with emphasis on packing parameters.