Aza-aromatic polycycles based on triphenylene and acridine or acridone: synthesis and properties

Abstract

Acridine- and acridone-based polycyclic aromatics were prepared by using as the key steps a copper-catalysed N-arylation of 2-aminobenzaldehyde, 2-aminophenones, or ethyl 2-aminobenzoate with 2-iodotriphenylene, and an acid-mediated cyclization. The regioselectivity of this intramolecular S_EAr reaction was studied by performing Hückel theory calculations on the precursors. Due to their structural similarity with some MALDI-MS matrices, two acridine-based polycycles were evaluated for this purpose. Finally, in view of structure–property relationships, preliminary studies of the photophysical properties of the synthesized acridine- and acridone-based polycycles were performed.