Tribenzo[27]crown-9: A new ring for dibenzylammonium rods

Stuart J. Cantrill, Matthew C T Fyfe, Aaron M. Heiss, J. Fraser Stoddart*, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

(formula presented) Dibenzylammonium (DBA+) ions thread through the cavity of tribenzo[27]crown-9 (TB27C9) to generate [2]pseudorotaxanes that are stabilized principally by hydrogen-bonding interactions. The stabilities and complexation kinetics associated with these pseudorotaxanes depend markedly on the nature of the substituents situated on the phenyl rings of the DBA+ ions. For example, the complex formed between TB27C9 and the DBA+ ion bearing electron-withdrawing P-CO2Me substituents is stronger than that obtained from TB27C9 and the "parent", unsubstituted DBA+ ion itself. Furthermore, the "parent" complex equilibrates much more rapidly with its uncomplexed components than do the complexes generated from TB27C9 and substituted DBA ions.

Original languageEnglish (US)
Pages (from-to)61-64
Number of pages4
JournalOrganic Letters
Volume2
Issue number1
StatePublished - Jan 1 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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