Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

A S 6-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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-05, Vol.143 (17), p.6498-6504
Main Authors: Picini, Flavio, Schneider, Susanne, Gavat, Odile, Vargas Jentzsch, Andreas, Tan, Junjun, Maaloum, Mounir, Strub, Jean-Marc, Tokunaga, Shoichi, Lehn, Jean-Marie, Moulin, Emilie, Giuseppone, Nicolas
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
Polymers
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Summary:A S 6-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).
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c00623