Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage

Severin Merget, Lorenzo Catti, Shani Zev, Dan T. Major, Nils Trapp, Konrad Tiefenbacher

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The sizes of available self-assembled hydrogen-bond-based supramolecular capsules and cages are rather limited. The largest systems have volumes of approximately 1400–2300 Å3. Herein, we report a large, hexameric cage based on intermolecular amide–amide dimerization. The unusual structure with openings, reminiscent of covalently linked cages, is held together by 24 hydrogen bonds. With a diameter of 2.3 nm and a cavity volume of ∼2800 Å3, the assembly is larger than any previously known capsule/cage structure relying exclusively on hydrogen bonds. The self-assembly process in chlorinated, organic solvents was found to be strongly concentration dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host–guest complexes with fullerenes (C60 and C70) was observed.

Original languageEnglish
Pages (from-to)4447-4453
Number of pages7
JournalChemistry - A European Journal
Volume27
Issue number13
DOIs
StatePublished - 1 Mar 2021

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Keywords

  • amides
  • fullerenes
  • host–guest complexes
  • self-assembly
  • supramolecular chemistry

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