Selective Self-Organization of Guest Molecules in Self-Assembled Molecular Boxes
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- 作者：Jessica M. C. A. Kerckhoffs ; Mattijs G. J. ten Cate ; Miguel A. Mateos-Timoneda ; Fijs W. B. van Leeuwen ; Bianca Snellink-Ruë ; l ; Anthony L. Spek ; Huub Kooijman ; Mercedes Crego-Calama ; and David N. R
- 刊名：Journal of the American Chemical Society
- 出版年：2005
- 出版时间：September 14, 2005
- 年：2005
- 卷：127
- 期：36
- 页码：12697 - 12708
- 全文大小：1073K
- 年卷期：v.127,no.36(September 14, 2005)
- ISSN：1520-5126
文摘
This article describes the synthesis and binding properties of highly selective noncovalentmolecular receptors 13·(DEB)6 and 33·(DEB)6 for different hydroxyl functionalized anthraquinones 2. Thesereceptors 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 ahighly 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 conformationfrom staggered to eclipsed upon complexation to afford a better fit for the 23 trimer. The receptor selectivitytoward different anthraquinone derivatives 2 has been studied using 1H NMR spectroscopy, X-raycrystallography, UV spectroscopy, and isothermal microcalorimetry (ITC). The 
- stacking between theelectron-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. Theselectivity of the hydrogen-bonded host for the anthraquinone derivatives is the result of steric interactionsbetween the guest molecules and the calix[4]arene aromatic rings of the host.
- stacking between theelectron-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. Theselectivity of the hydrogen-bonded host for the anthraquinone derivatives is the result of steric interactionsbetween the guest molecules and the calix[4]arene aromatic rings of the host.