Stable heterotopic noncovalent resorcin[4]arene assemblies

Irene Higler, I. Higler, Lennart Grave, Esther Breuning, Willem Verboom, Feike de Jong, Thomas M. Fyles, David Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

34 Citations (Scopus)

Abstract

Resorcin[4]arene tetracarboxylic acids 5,6 (A) and resorcin[4]arene tetrapyridines 2,3 (P) self-assemble in chloroform solution to form stable heterotopic AP dimers. Data from NMR titration and dilution experiments, as well as from vapor-pressure osmometry (VPO), indicate that the AP dimer is formed with an association constant greater than 107 M-1. Solid-solution extraction experiments are indicative of the formation of a 2:1 trimer (A2P), while self-associated homotopic species (A2 and A3) can be detected by NMR and VPO. Analysis of the heterotopic noncovalent assembly process over a range of compositions shows that these other species are much less stable than the AP heterodimer, which is the exclusive species at an A/P concentration ratio of 1:1 (> 99.7% of the total at 10 mM).
Original languageUndefined
Pages (from-to)1727-1734
JournalEuropean journal of organic chemistry
Issue number9
DOIs
Publication statusPublished - 2000

Keywords

  • METIS-106274
  • IR-11660
  • Resorcin[4]arenes
  • Vapor-pressure osmometry
  • Self-Assembly

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