Selective self-organization of guest molecules in self-assembled molecular boxes


Kerckhoffs, Jessica M.C.A. and Cate, M.G.J. ten and Mateos Timoneda, Miguel A. and Leeuwen, Fijs W.B. van and Snellink-Ruël, Bianca H.M. and Spek, Anthony L. and Kooijman, Huub and Crego Calama, Mercedes and Reinhoudt, David N. (2005) Selective self-organization of guest molecules in self-assembled molecular boxes. Journal of the American Chemical Society, 127 (36). pp. 12697-12708. ISSN 0002-7863

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Abstract:This article describes the synthesis and binding properties of highly selective noncovalent molecular receptors 13·(DEB)6 and 33·(DEB)6 for different hydroxyl functionalized anthraquinones 2. These receptors are formed by the self-assembly of three calix[4]arene dimelamine derivative molecules (1 or 3) and six diethylbarbiturate (DEB) molecules to give 13·(DEB)6 or 33·(DEB)6. Encapsulation of 2 occurs in a highly organized manner; that is, a noncovalent hydrogen-bonded trimer of 2 is formed within the hydrogen-bonded receptors 13·(DEB)6 and 33·(DEB)6. Both receptors 13·(DEB)6 and 33·(DEB)6 change conformation from staggered to eclipsed upon complexation to afford a better fit for the 23 trimer. The receptor selectivity toward different anthraquinone derivatives 2 has been studied using 1H NMR spectroscopy, X-ray crystallography, UV spectroscopy, and isothermal microcalorimetry (ITC). The - stacking between the electron-deficient center ring of the anthraquinone derivatives 2a-c and 2e-g and the relatively electron-poor melamine units of the receptor is the driving force for the encapsulation of the guest molecules. The selectivity of the hydrogen-bonded host for the anthraquinone derivatives is the result of steric interactions between the guest molecules and the calix[4]arene aromatic rings of the host.
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Copyright:© 2005 American Chemical Society
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