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Strauss, Michael J; Jia, Manping; Evans, Austin M; Castano, Ioannina; Li, Rebecca L; Aguilar-Enriquez, Xavier; Roesner, Emily K; Swartz, Jeremy L; Chavez, Anton D; Enciso, Alan E; Stoddart, J. Fraser; Rolandi, Marco; Dichtel, William R
Journal of the American Chemical Society, 06/2021, Volume: 143, Issue: 21Journal Article
Macrocycles that assemble into nanotubes exhibit emergent properties stemming from their low dimensionality, structural regularity, and distinct interior environments. We report a versatile strategy to synthesize diverse nanotube structures in a single, efficient reaction by using a conserved building block bearing a pyridine ring. Imine condensation of a 2,4,6-triphenylpyridine-based diamine with various aromatic dialdehydes yields chemically distinct pentagonal 5 + 5, hexagonal 3 + 3, and diamond-shaped 2 + 2 macrocycles depending on the substitution pattern of the aromatic dialdehyde monomer. Atomic force microscopy and in solvo X-ray diffraction demonstrate that protonation of the macrocycles under the mild conditions used for their synthesis drives assembly into high-aspect ratio nanotubes. Each of the pyridine-containing nanotube assemblies exhibited measurable proton conductivity by electrochemical impedance spectroscopy, with values as high as 10–3 S m–1 (90% R.H., 25 °C) that we attribute to differences in their internal pore sizes. This synthetic strategy represents a general method to access robust nanotube assemblies from a universal pyridine-containing monomer, which will enable systematic investigations of their emergent properties.
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