Stable heterotopic noncovalent resorcin[4]arene assemblies

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

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

25 Citations (Scopus)
2 Downloads (Pure)


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 languageEnglish
Pages (from-to)1727-1734
JournalEuropean journal of organic chemistry
Issue number9
Publication statusPublished - 2000


  • Resorcin[4]arenes
  • Vapor-pressure osmometry
  • Self-Assembly


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