Composition- and Size-Controlled Cyclic Self-Assembly by Solvent- and C60-Responsive Self-Sorting

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• 作者：Qixun Shi ; Karl-Erik Bergquist ; Ruiping Huo ; Jilai Li ; Mikael Lund ; Robert V谩cha ; Anders Sundin ; Eugenijus Butkus ; Edvinas Orentas ; Kenneth W盲rnmark
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：October 9, 2013
• 年：2013
• 卷：135
• 期：40
• 页码：15263-15268
• 全文大小：422K
• 年卷期：v.135,no.40(October 9, 2013)
• ISSN：1520-5126

文摘

Synthesis, solvent-, and guest-controlled self-assembly, and self-sorting of new hydrogen-bonded chiral cavity receptors are reported. The design of the cavity is based on the cyclic self-aggregation of monomers containing the 4H-bonding ureidopyrimidinone motif fused with the bicylo[3.3.1]nonane framework. Selective formation of kinetically inert cyclic tetramers is observed in chloroform, while in toluene an equilibrium between tetrameric and pentameric forms exists. The high affinity of the tetrameric aggregates toward C₆₀ and C₇₀ is observed in aromatic solvents. The host鈥揼uest interaction of unconventional 蟺-acidic supramolecular receptors for fullerenes is turned off and on by changing the solvent, whereas the selection of size and the very composition of the cavity aggregate is controlled by either the change of solvent or the addition of fullerene guest, making our systems a new type of self-sorting device.