Self-Assembly of a Water-Soluble Tricyclic Heterocycle into J-Type Rosette Nanotubes

The synthesis and self-assembly of a water-soluble, tricyclic, self-complementary heterocycle that features the hydrogen bond donor-acceptor arrays of both guanine (G) and cytosine (C) juxtaposed between a pyridine ring is presented. In solution, this tricycle, which has been termed xK1, self-assembles into Rosette Nanotubes (RNTs) that have an inner diameter of 1.4 nm. Unlike the RNTs formed from the bicyclic congener K1, we demonstrate that xK1 with its extended ð system, forms a J-type RNT assembly determined through UV-Vis, CD and fluorescence spectroscopy experiments. This observation brings the possibility of developing electrically conducting RNTs for applications in the areas of photovoltaics and molecular wires.