Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly

Anton D. Chavez, Austin M. Evans, Nathan C. Flanders, Ryan P. Bisbey, Edon Vitaku, Lin X. Chen, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Scopus citations


Macrocycles based on directional bonding and dynamic covalent bond exchange can be designed with specific pore shapes, sizes, and functionality. These systems retain many of the design criteria and desirable aspects of two-dimensional (2D) covalent organic frameworks (COFs) but are more easily processed. Here we access discrete hexagonal imine-linked macrocycles by condensing a truncated analogue of 1,3,5-tris(4-aminophenyl)benzene (TAPB) with terephthaldehyde (PDA). The monomers first condense into polymers but eventually convert into hexagonal macrocycles in high yield. The high selectivity for hexagonal macrocycles is enforced by their aggregation and crystallization into layered structures with more sluggish imine exchange. Their formation and exchange processes provide new insight into how imine-linked 2D COF simultaneously polymerize and crystallize. Solutions of these assembled macrocycles were cast into oriented, crystalline films, expanding the potential routes to 2D materials.

Original languageEnglish (US)
Pages (from-to)3989-3993
Number of pages5
JournalChemistry - A European Journal
Issue number16
StatePublished - Mar 15 2018


  • covalent organic frameworks
  • dynamic covalent chemistry
  • imines
  • self-assembly
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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