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Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes.

Flavio PiciniSusanne SchneiderOdile GavatAndreas Vargas JentzschJunjun TanMounir MaaloumJean-Marc StrubShoichi TokunagaJean-Marie LehnEmilie MoulinGiuseppone Nicolas
Published in: Journal of the American Chemical Society (2021)
A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]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).
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