Conjugated Macrocycles in Organic Electronics

ConspectusThis Account describes a body of research on the design, synthesis, and application of a new class of electronic materials made from conjugated macrocycles. Our macrocyclic design takes into consideration the useful attributes of fullerenes and what properties make fullerenes efficient n-type materials. We identified four electronic and structural elements: (1) a three-dimensional shape; (2) a conjugated and delocalized π-space; (3) the presence of an interior and exterior to the π-surface; and (4) low-energy unoccupied molecular orbitals allowing them to accept electrons. The macrocyclic design incorporates some of these properties, including a three-dimensional shape, an interior/exterior to the π-surface, and low-lying LUMOs maintaining the n-type semiconducting behavior, yet we also install synthetic flexibility in our approach in order to tune the properties further.Each of the macrocycles comprises perylenediimide cores wound together with linkers. The perylenediimide building block endows...