Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[1(6)]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).

Automated summary

A S6-symmetric triarylamine-based macrocycle decorated with six lateral amide functions is synthesized and shown to undergo supramolecular polymerization in specific solvent to form nanotubular structures. Spectroelectrochemical analysis reveals extended electronic delocalization of charge carriers within the macrocycles and between the macrocycles during sequential oxidation.