Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Michael J. Strauss, Manping Jia, Austin M. Evans, Ioannina Castano, Rebecca L. Li, Xavier Aguilar-Enriquez, Emily K. Roesner, Jeremy L. Swartz, Anton D. Chavez, Alan E. Enciso, J. Fraser Stoddart, Marco Rolandi, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)8145-8153
Number of pages9
JournalJournal of the American Chemical Society
Issue number21
StatePublished - Jun 2 2021

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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