N-Heterotriangulenes: Fascinating Relatives of Triphenylamine

Abstract

Carbonyl- and dimethylmethylene-bridged triphenylamines called N-heterotriangulenes are not only aesthetically pleasing π-conjugated scaffolds interesting on their own but also provide numerous possibilities for further synthetic modifications to serve as versatile precursors for the construction of functional organic molecules. In this Personal Account we give a historical synopsis depicting the long way from the initial synthesis of N-heterotriangulenes back in the 1970s to their derivatization followed by recent applications in organic electronics. As a part of our ongoing research on heteroatom-doped π-conjugated scaffolds we provide an overview of our synthetic efforts involving the N-heterotriangulene scaffolds and discuss the optoelectronic, redox, and self-assembly properties of the resulting molecular entities.

Keywords: aromaticity; heterocycles; polycyclic aromatic hydrocarbons; push-pull chromophores; self-assembly.