π-Stacking Stopper-Macrocycle Stabilized Dynamically Interlocked [2]Rotaxanes

Sing Ming Chan, Fung Kit Tang, Ching Yau Lam, Chak Shing Kwan, Sam C.K. Hau*, Ken Cham Fai Leung

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of mechanically interlocked molecules is valuable due to their unique topologies. With π-stacking intercomponent interaction, e.g., phenanthroline and anthracene, novel [2]rotaxanes have been synthesized by dynamic imine clipping reaction. Their X-ray crystal structures indicate the π-stackings between the anthracene moiety (stopper) on the thread and the (het-ero)aromatic rings at the macrocycle of the rotaxanes. Moreover, the length of glycol chains affects the extra π-stacking intercomponent interactions between the phenyl groups and the dimethoxy phenyl groups on the thread. Dynamic combinatorial library has shown at best 84% distribution of anthracene-threaded phenanthroline-based rotaxane, coinciding with the crystallography in that the additional π-stacking intercomponent interactions could increase the thermodynamic stability and selectivity of the rotaxanes.

Original languageEnglish
Article number4704
JournalMolecules
Volume26
Issue number15
DOIs
Publication statusPublished - 3 Aug 2021

Scopus Subject Areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

User-Defined Keywords

  • Dynamic combinatorial library
  • Imine macrocycle
  • Intercomponent interaction
  • Rotaxane synthesis
  • π-stacking

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