(Invited) Making Stacks of Nitrogenated Polycyclic Aromatic Hydrocarbons with Hydrogen Bonds

Abstract

Architectures constituted of stacked aromatics play a crucial role in the development of function in biomacromolecules. Recreating this feature on synthetic systems would not only allow understanding and reproducing biological functions but also developing new functions. For instance, the performance of organic field-effect transistors, light-emitting diodes, and solar cells critically depends on the charge transport efficiency of stacks of organic semiconductors. Among different packing configurations, lamellar π-stacking has been identified as an optimal configuration for electronic transport, because of the efficient intermolecular electronic coupling.Nitrogenated polycyclic aromatic hydrocarbons and nanographenes have attracted considerable attention in recent years. Besides the effect of nitrogen doping on the electronic structure, sp2 nitrogens can be engaged in hydrogen bonding interactions as acceptors. We have developed the synthesis of novel architectures constituted of stacked nitrogenated polycyclic aromatic hydrocarbons held together by hydrogen bonds, which include new families of pseudorotaxanes, rotaxanes, foldamers and supramolecular polymers. The synthesis and self-assembling properties of these systems will be discussed together with their charge transporting properties.