Structure-directed synthesis of polyacene derivatives

Abstract

The synthesis of a range of novel polycyclic and macropolycyclic molecular structures has been achieved. By dictating the outcome of these cycloaddition reactions through the utilization of stereoelectronic information that is pre-programmed into the π-systems of each building block, we have shown that the structures of the products can be imagined and attained in a kinetically-controlled substrate-directed Diels-Alder oligomerization sequence. The use of building blocks possessing different topologies and heteroatom substitutions will provide access to a wide range of outwardly-complex molecular structures. Further to being appealing synthetic targets in their own right, these polyacene derivatives represent useful precursors to a wide range of novel unsaturated and saturated hydrocarbon structures.