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

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Authors	SHI Q. BERGQUIST K.-E. HUO R. LI J. LUND M. VÁCHA Robert SUNDIN A. BUTKUS E. ORENTAS E. WÄRNMARK K.
Year of publication	2013
Type	Article in Periodical
Magazine / Source	J AM CHEM SOC
MU Faculty or unit	Central European Institute of Technology
Citation
Web	http://pubs.acs.org/doi/pdf/10.1021/ja408582w
Doi	http://dx.doi.org/10.1021/ja408582w
Field	Biochemistry
Keywords	SUPRAMOLECULAR CHEMISTRY; NONCOVALENT SYNTHESIS; FULLERENES; ACID; CUCURBITURIL; RECOGNITION; SYSTEMS; HOSTS; CYCLODEXTRIN; COMPLEXATION
Description	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 C-60 and C-70 is observed in aromatic solvents. The host guest interaction of unconventional pi-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.