Triazatriangulenium salts – hosts and guests in supramolecular assemblies in solution

Abstract

Self-assembly of triazatriangulenium dyes (TATA) bearing C3-C8 substituents and their interaction with aromatic compounds were studied. The dyes with alkyl chains longer than C5 were strongly aggregated in solution, while those with shorter alkyl chains formed hetero-stacks with aromatic compounds in chloroform. Anthracene, pyrene, coronene, and a naphthalene diimide dye formed heterostacks in solution with association constants 10⁴ M⁻¹. Anthracene and pyrene-based water-soluble cyclophanes were designed to investigate host–guest complexes with TATA dyes in an aqueous solution. Experimental and theoretical investigations suggest that only pyrene-based cyclophane is able to encapsulate TATA dyes. These self-assembled structures constitute new supramolecular motifs to construct multilayered organic structures.