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*

*この研究の対応する著者

研究成果: Article査読

28 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4390-4402
ページ数13
ジャーナルJournal of Organic Chemistry
69
13
DOI
出版ステータスPublished - 2004 6月 25
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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