期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 12, 页码 3310-3319出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500976
关键词
cavitands; metal coordination; molecular recognition; self-assembly; supramolecular chemistry
The synthesis and spectroscopic characterization of a cavitandbased coordination capsule 1(.)4BF(4) of nanometer dimensions is described. Encapsulation studies of large aromatic guests as well as aliphatic guests were performed by using H-1 NMR spectroscopy in [D-1]chloroform. In addition to the computational analysis of the shape and geometry of the capsule, an experimental approach to estimate the interior size of the cavity is discussed. The cavity provides a highly rigid binding space in which molecules with lengths of approximately 14 angstrom can be selectively accommodated. The rigid cavity distinguished slight structural differences in the flexible alkyl-chain guests as well as the rigid aromatic guests. The detailed thermodynamic studies revealed that not only CH-pi interactions between the methyl groups on the guest termini and the aromatic cavity walls, but also desolvation of the inner cavity play a key role in the guest encapsulation. The cavity preferentially selected the hydrogen-bonded heterodimers of a mixture of two or three carboxylic acids 1.8-20. The chiral capsule encapsulated a chiral guest to show diastereoselection.
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