Polyvalent interactions in unnatural recognition processes

James N. Lowe, David A. Fulton, Sheng Hsien Chiu, Arkadij M. Elizarov, Stuart J. Cantrill, Stuart J. Rowan, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The synthesis of two cluster compounds, one containing six secondary dialkylammonium ion centers and the other possessing six benzo-m-phenylene[25] crown-8 (BMP25C8) macrocycles, both appended to hexakis(thiophenyl)benzene cores, is described. The binding of these clusters with complementary mono- and divalent ligands is investigated with NMR spectroscopy to probe polyvalency in these unnatural recognition systems. The ability of the two different families of clusters to bind complementary monovalent ligands is compared with that of the monovalent receptor pair, namely the dibenzylammonium ion and BMP25C8. This comparison is made possible by determining an average association constant (KAVE) for the binding of each recognition site on the cluster with the corresponding monovalent ligand. We have found that the clustering of recognition sites together in one molecule is detrimental to their individual abilities to bind monovalent ligands. In the case of the polyvalent interaction between the hexakisBMP25C8 cluster and divalent dialkylammonium ions, an association constant, KPOLY, was calculated from the value of K AVE determined for the complexation of the individual component recognition sites. This polyvalent interaction is significantly stronger than that associated with the averaged monovalent interactions.

Original languageEnglish
Pages (from-to)4390-4402
Number of pages13
JournalJournal of Organic Chemistry
Volume69
Issue number13
DOIs
Publication statusPublished - 2004 Jun 25
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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